In other words, San Diego Magazine’s November 2005 cover is wild. And inside waits a huge feature on dating in SD. I had questions. So many questions. Is anything different about SD’s dating scene nearly 20 years later?

“If there are plenty of fish in the sea, why haven’t you hooked one?” the article’s subhead asks. “A look at the up-and-down dating life of San Diegans—and how to make the perfect catch. Maybe.” 

Writer Amber Cyphers goes on to wonder, “With one million people in the city, why is it still so hard to find love?”

This sounds familiar.

“We asked a group of very dateable San Diegans for their take on the world of singles, and did some research of our own,” Cyphers writes. “It was illuminating, to say the least, although there was no consensus on the best way to meet other singles in San Diego. Not surprisingly, few found much success developing lasting relationships with people they met in bars. Beyond that, it was a tossup.”

This could have been written today. I am Cyphers, and she is me. We’ve come so far since the dating-app-free world of yesteryear… while also seemingly going nowhere at all. Great news for singles.

Luckily, the piece offers some tips about where to meet local singles. Cyphers suggests checking out social events hosted by arts institutions like The Old Globe, returning to school to take extension courses (this seems a bit much), frequenting your neighborhood coffee shop to find “local delights” posted on its notice boards, and getting into sports. 

Did you know there was once an Athletic Singles Association? Or an org called the Single Sierrans, a subgroup of the local Sierra Club, an environmental protection organization, for people in their 20s and 30s? 

Back then, online dating was relegated to sites like Match.com or HurryDate.com—which may have been the prototype for Tinder, though I can’t be sure.

Instead of my typical article this week, we’re going back in time to hear the stories of other singles looking for love. Because look, it’s not you—it really is that hard and weird and confusing. Grab a glass of wine and some popcorn and get cozy with the tales of San Diego’s most eligible Y2K bachelors and bachelorettes.

Also, if you’re one of the singles profiled in this feature, please email us and let us know if you found love… especially if it was because you went back to college.

Meet Justin, a 28-year-old Oklahoman who discovered why San Diego is such a great place for burgeoning Peter Pans. 

On the next page, Lisa Feinstein, a 35-year-old healthcare professional, shares her dating horror stories. Offering to find your date a sugar daddy—totally wack or kinda chivalrous in this economy? You decide. 

Here we have 35-year-old Summer Morse, who offers some sound advice and an optimistic outlook for singles. “I’m looking for a relationship full of integrity and communication—having the understanding that falling in and out of love happens, and it’s okay,” she says.

Travis Bone, on the other hand, found that a little wine with a side of pretension is a good reminder that being single may not be so bad after all. 

Tom Chambers’ story might be my favorite of the bunch. A tale as old as time: You and your situationship decide to take separate trips for New Year’s Eve. You head to Lake Tahoe; she jets off to Miami. A week later, you turn on the Lakers game and see her courtside… with another dude. Ouch. 

A holistic healthcare practitioner and divorcée, 46-year-old Lilia Gudiño-Vazquez is perfectly fine with her relationship status. The single mom of two reminds us that dating in your 40s means you’re no longer comfortable wasting your time with things that don’t add value to your life.

At 48, executive assistant Lisa Schiff signed up for what she called “on-line personals.” She’s excited about the idea of a younger man, unless he wants children. How very Anne Hathaway in The Idea of You. 

Finally, 28-year-old Nam Chantepie offers a cute metaphor about the dating pool. “Sometimes I feel like there needs to be more chlorine in that pool, but I keep floating along in my water wings, waiting to bump into someone else who wants to play Marco Polo,” he says. I genuinely hope he found his mermaid.

So, if you’re single, is there comfort knowing that dating in SD has always been challenging? Or did you find love here decades ago—and think that you left the market when things were easier? Either way, we would love to hear from you. Email us at [email protected].

If you’re new to Unhinged, catch up on all the dating chats you’ve missed here and follow along at @monicles and @sandiegomag on Instagram to know when a new article drops each week.

Sign-up now for the Unhinged newsletter for exclusive content, Q&As with Nicolle, and subscriber-only meet-ups!

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The post Unhinged, A Dating Series: 20 Years Later, We’re Still Single appeared first on San Diego Magazine.

I met Underhill in my DMs. After reading one of my pieces, the 38-year-old whiskey brand ambassador wrote to me to share about a relationship that had started right before the pandemic and ended in a FaceTime breakup three years later (and two days before Christmas). Damn.

As she drove home from Palm Springs one afternoon, we hopped on a call to chat about her experiences dating in the city. I wanted to know if the feelings I had about dating were the same as others or if I really was on an island of my own making. We connected on something over the course of our conversation: Dating has felt different—and more difficult—for both of us since the advent of the pandemic. For Underhill, the realization occurred when she tried revisiting dating apps in 2022.

That digital space was suddenly a new world—just like the one outside of it, filled with people fatigued by years of uncertainty and isolation.

“I got on Bumble and Hinge and immediately felt 25 years older than I actually am. I felt so confused by the technology that I used to know so well,” says Underhill, a Seattle native who moved to San Diego eight years ago. “I was like, ‘What are all these premium features? What are all these new things?’”

Combing through profiles, swiping, chatting, flirting, cringing, getting left on read—it all felt strange. Underhill remembers thinking that Covid and social distancing affected how everyone communicated.  

“I was trying to register these changes. What’s different about me? What’s different about the world?” she says. “I kind of felt almost instinctively like [I wanted] to internalize it, like it was something different I was doing. Then I realized we just all went through this huge global change. I think the pandemic reframed our brains on a lot of things.”

Collectively, we’ve changed. It can’t be ignored that, four years later, we’re still somewhat socially rusty. Last year, a poll conducted for Newsweek showed that 42 percent of participants admitted to being less sociable than in 2019.

We’re exhausted. This is potentially the most don’t-talk-to-me-I’d-rather-stay-home era we’ve had in a long time, which doesn’t make for the most ideal setting to find love. I recently read a headline declaring that “lockdowns turned us into antisocial goblins,” and, honestly, that’s not wrong. 

Research also points to people withdrawing rather than seeking connection when they experience loneliness—meaning that, throughout the pandemic, as many struggled with feelings of depression, it actually began to change how they interacted with others and affected their ability to seek out relationships. 

“Connection has become so accessible that people don’t treat it as special anymore,” Underhill says. I get it. She’s hitting on something that many of us feel but can’t exactly explain. Covid took a toll on us all, and we’re lucky to be approaching some sort of normalcy these days.

The thing is, though, the internet provides a pretty cozy place to retreat to with all your “friends.” Between the parasocial sense of “hanging out” with your favorite podcasters, curling up with virtual girlfriends during a 50-part TikTok series, or getting that quick dopamine hit of matching (but never actually talking) on dating apps, we assuage our loneliness with low-stakes activities. 

These new antisocial behaviors could be a big part of why dating seems so much more difficult. Those who may have once spent their weekends at bars, sports events, concerts, or dinner parties are now holed up at home, where meet-cutes don’t really happen. (Unless your UberEats driver happens to be hot and single.) 

And, even if people are swiping from their couches, not all of them are seeking love—or even a fling. They may just want momentary connection.

Both men and women on the subreddit r/OnlineDating have complained that their matches never seem interested in actually meeting. So, how do we weed out those who are swiping just for a self-esteem boost, and how do we meet people organically in an increasingly isolated world?

If writing this column has taught me anything, it’s that being vulnerable allows others to be the same. Like Underhill, many people have reached out to me—a complete stranger—to share their need for connection. And potential dates have shot their shot knowing that I’m looking for something real.

My situation is unique; I’m not unaware of that fact. But for some, getting “out there” again may just mean hitting an Instagram social meet-up with friends and committing to talking to at least two people you don’t know. Or, it’s forgoing the standard answers on your Hinge profile and clarifying exactly what you’re looking for.

So, if you’re searching for love and the apps aren’t cutting it, or the meet-ups aren’t happening, it’s time to get up off the couch and back into the world in a pre-pandemic kind of way. Hit the bar, organize a dinner party, take yourself on a solo date with a book, or buy tickets to the next Wave FC game. Your chances increase the more you leave your house. 

Digging deeper with people is riskier than the safety of scrolling or swiping (trust me, I know!). But because of that, the rewards are far bigger, too.

I’d love to hear your thoughts and what you’re doing to help yourself return to a more sociable you. As for Underhill, she remains hopeful. She’s still using the apps, making the first move with a gif of Forrest Gump waving hello, and switching her perspective on the Covid slump.

“I was just thinking that my biggest nightmare at the gym would be me using a machine and somebody coming over and correcting me because I just feel like it would be so embarrassing,” she says. “But then I was like, I’m describing a meet-cute.”

We’re all struggling, she reminds me, but maybe that’s part of what may bring us together at the end of the day. “I do feel like there’s some reassurance knowing that it’s not me. The scene is very hard,” she says. “I’m hoping that maybe we’re just kind of like the foot soldiers, like the infantry, connecting with singles for the sake of solidarity and friendship.”

If you’re new to Unhinged, catch up on all the dating chats you’ve missed here and follow along at @monicles and @sandiegomag on Instagram to know when a new article drops each week.

Sign-up now for the Unhinged newsletter for exclusive content, Q&As with Nicolle, and subscriber-only meet-ups!

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The post Unhinged, A Dating Series: Finding Connection in A Disconnected World appeared first on San Diego Magazine.

At the time, the young man had been doing a handstand on his skateboard past her privacy hedge. She could only see his red shoes as he passed by. “The rest is history,” she laughed. 

My date looked at me, and smirked, “This is a good sign.”

I met Caleb (not his real name) through this column. He slid into my DMs after the first post went live, thanking me for understanding what it’s like out there. I hadn’t thought much of it at the time. I had plenty of those types of messages, along with 500 new followers in one day. When I started reaching out to a handful of locals who had messaged me to do some research and interviews, I remembered to go back to his profile.

He was intriguing, listed a bunch of hobbies on his Instagram which was filled with photos of travels. Noticeably absent, however, were pictures of his face. After reaching out for a chat, we scheduled a call a week later to talk about his dating history and the challenges he was facing as a man in his late 30s. For me, this was purely research for my burgeoning column, or so I thought.

There was an ease to our conversation on the phone. Caleb was open and honest, it didn’t feel like he was putting on a show. Still, though, I could hear some inconsistencies in what he was saying and wrote him off as someone who wasn’t ready to date.

Weeks later, I got a text from him asking me out. “Hey would you wanna get a drink sometime?” he wrote. Short and to the point, there had been no messages leading up to this. But Khruangbin, a band whose name I still can’t pronounce, was playing at the Shell and he wanted to take me. I was in. 

A week later, we stood on the grass with VIP bracelets (he wanted me to be able to see, he said) discussing his red shoes. He was cuter than I expected. We talked like old friends, plenty of banter and no uncomfortable moments of silence. With a bottle of red and two wine glasses, we spent the evening chatting, laughing, and flirting.

He was child-like, overly excited to be spending time with me, giddy even. “Your eyes are like a garden,” he said at one point, calling out their hazel coloring. It wasn’t meant to be romantic, I don’t think, he was more blurting out the first thoughts that came to his mind as I took off my sunglasses. But I liked it.

I’m used to fighting for someone’s affection, so feeling wanted is new for me. And Caleb had done his homework, recalling past articles as he asked questions about me. He had clicked on each Unhinged article to learn everything he could.

“Neither,” he had chosen a couple weeks earlier when I had polled readers about which guy I should date between Ryan and Connor. He was paying attention.

Before the headliner, we got another bottle of wine. “The second one has to be more expensive, right? To show your date you’re interested?” he said. Noted. By the end of the evening, I wanted to kiss him. If you’ve been reading this column since the start, you’ll know this isn’t typical for me on first dates. 

A good sign.

As my Uber approached at the end of the night, he asked if he could kiss me. It was simple, sweet. “Send me a text when you get home,” he said as he closed the car door. He asked me out the next morning and we made actual plans. We’ve talked every day since—he gave me his phone’s passcode.

If I’m being honest, I didn’t want to write this post. This is a world of false starts and normally, those conversations exist only between friends and over text. If this goes nowhere, thousands of readers will know. It’ll be embarrassing. But I didn’t start this column to paint an unrealistic picture of dating. There will be lessons learned through Caleb, whether he remains in my life for a week, a season, or more.

Here’s the thing, at the end of the day it’s maybe not that complicated to show someone you’re interested in them. I think Caleb could teach a masterclass on catching a woman’s attention. He made a thoughtful first move. He took me on a cool first date, wasn’t afraid to flirt up a storm, yet remained respectful and didn’t push. He asks questions. He shows actual interest, and doesn’t (yet, at least) leave me guessing if I matter to him. Hell, he even reads my work. So for what it’s worth, hope you’re taking notes, gents.

Oh, and if you’re wondering, he no longer reads the column. “I want you to keep being completely honest with it, that’s what makes it so good…,” he texted. “If you know that I’ll eventually read it, you may alter it in some way that you wouldn’t have previously and I don’t want to do that to you and it.”

For those of you in relationships, I’m curious, what did you do to make your partner fall for you? How did you impress? Did you spring for the expensive bottle, write a love song, or do a handstand on your skateboard? Email us at @[email protected] with your story and a chance to be featured in the Unhinged newsletter.

If you’re new to Unhinged, catch up on all the dating chats you’ve missed here and follow along at @monicles and @sandiegomag on Instagram to know when a new article drops each week.

Sign-up now for the Unhinged newsletter for exclusive content, Q&As with Nicolle, and subscriber-only meet-ups!

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The post Unhinged, A Dating Series: It’s Not That Complicated appeared first on San Diego Magazine.

Getting real with you all each week has been fun, eye-opening, and anxiety-inducing (please send nice messages on Thursday nights). Recently, I took the time to think about what lessons have come from my adventures and my chats with readers and friends. I share those insights below.

While there are still more vulnerable pieces of me that I’m not ready to share yet publicly—like the lingering effects of my past relationship—having so many new friends rooting for me and sharing their own stories has been incredibly humbling in the best way. I’m the most hopeful I’ve ever been that maybe we can figure this out together.

So, here are five things I’ve learned since starting this column:

Men are struggling, too

As a woman, it can be easy to fall into the trap of thinking men have it easy when it comes to heterosexual dating (stay tuned for guest columnists speaking to other types of relationships). It’s not uncommon to hear women complaining about men’s reluctance to commit and about how hard it is to find someone genuine. 

I’ve been surprised, though, at the amount of men who have written to me to say thank you for this series. They’ve shared their stories, opened up to me personally about unrequited love, and took the time to reflect on some of the things I have written about. Many have also said that they don’t speak about this stuff to anyone. 

In a society where little boys are taught to hold their feelings in, hopefully more men will start to see the benefit in talking out their emotions with friends or seeking advice from experienced professionals such as therapists. After all, you can’t know what you don’t know, and sometimes the best advice will come from those with unbiased opinions. 

Dating is a numbers game

I’ve never dated so much in my life. With my matchmaker setting me up with potential suitors, DMs rolling in from readers of this column, and friends introducing me to their single pals, it’s been overwhelming (and a little exhausting). 

Most of the dates I’ve been on haven’t led to a second date, but they have taught me more about what I want, what I’m willing to potentially compromise on, and what I need to work on personally in romantic connections.

Expecting to find “the one” by only going on one or two dates every few months means that you’re significantly lowering your chances. Get outside, invest in hobbies that you love, head out to happy hours, sign up for classes, keep swiping (if you’re into that kind of thing), take chances on strangers at bars, say “yes” to everything—you never know who you may meet. 

What you ask is just as important as doing the actual asking

One of the biggest things I hear from women is that men don’t ask any questions on dates. It’s not completely a gendered issue, but research shows that men and women are taught to approach conversations differently. 

After I wrote about this, we got a flood of comments on our Instagram post and in my inbox from people who could relate. It seems obvious, but if you’re out there and dating, just ask a question—it may lead to your next relationship. 

But what you ask also matters. During a singles mixer this past February, matchmaker Sophy Love walked participants through some dating exercises with a focus on first-date questions. We learned that asking deeper, more emotionally driven questions tends to make people feel more connected to the asker. 

I genuinely became more interested in the people sitting across from me during the exercise. So skip the “what do you do for a living” questions and ask what childhood memory stands out as one of their favorite experiences. 

People will put in the effort when they’re interested

One of the first people I met during this column was a guy who I was very attracted to but who was only putting in the bare minimum when it came to dating me. He was cute and we had fun, but he only made plans with me last minute and made me feel like an afterthought. 

I remember telling him that I would like him to be intentional if he really was looking to get to know me. We ended things. 

There are people out there who will make it clear that they are wanting to get to know you and will make time to do so—and desiring that effort is not too much to ask. But we have to be willing to ask for what we want and be willing to walk away if they can’t provide it. I’ve also learned recently that the ones who are ready to be in a relationship won’t leave you guessing about future dates. You won’t be an afterthought. 

You can have it all

I recently asked the question, “Can you really have it all when it comes to love?” Stability, support, and compatibility and butterflies, passion, and bedroom chemistry with someone? At a certain age, we can start to feel the pressure to settle to avoid being alone.

Recently, I met someone who is making me believe that it’s possible to find a person who meets all your needs and wants. We’ve only been talking for a short time, but he’s unknowingly helping me heal from the trauma of a past relationship by being incredibly kind, honest, and intentional. On the other hand, I get nervous and excited to see him, something I’ve been missing in the past few dates.

I don’t know if this connection will turn into anything more. But what it is giving me is hope that I don’t have to settle for anything less than amazing. Fairytale romances aren’t just a thing in storybooks.  

If you’re new to Unhinged, catch up on all the dating chats you’ve missed here and follow along at @monicles and @sandiegomag on Instagram to know when a new article drops each week.

Sign-up now for the Unhinged newsletter for exclusive content, Q&As with Nicolle, and subscriber-only meet-ups!

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The post Unhinged, A Dating Series:  What Looking for Love Taught Me appeared first on San Diego Magazine.

Looking back, though, money issues never affected us. We made what we made, had the debt we had, and lived comfortably according to those metrics. We went on vacations, ordered takeout often, splurged on fine-dining restaurants, and counted sailing as one of our regular hobbies (hint: it’s not cheap).

And still, money was constantly cited as a reason (among others) why things couldn’t progress.

It’s a common theme. Financial security has been a consistent thread in my relationships and in my conversations, mostly with men, about what someone needs before trading singledom for a committed relationship. 

Greg (not his real name), my friend of about six years, is one of these men.

“There’s a variety of reasons [why I’m not in a relationship], but it all relates back to money. I don’t want to be a burden to any partner,” Greg says. “I have student debt that I always wanted to pay off well before I get married.”

When I talked to him about dating recently, he cited finances as a major reason why, at 38, he’s still not ready to have a girlfriend. 

At the start of 2020, Greg and I briefly dated—we made it about two months before realizing we had no long-term potential. He’s still one of my favorite people, though. He’s thoughtful, funny, and caring, and I sometimes wondered why he’s remained single.

Greg’s been off dating apps for a few years now. “If it happens, it happens,” he says, while also making it clear that he won’t be truly ready until his debt is paid off.

Sounds all too familiar. 

“I want to have the stability, or I want to have this perceived notion of stability through some metrics that I come up with and say, like, ‘Yes, I have the job and the right money where I feel somewhat okay with taking my eyes off of this section of things,’” Greg says.

For as long as I’ve known him, he’s had a stable job and made good money. From the other side of the phone, this feels like an excuse, a faulty plan that may leave him missing out on some really great women. I ask him what “financial stability” means.

His markers, he replies, involve paying off his debt and feeling secure in his job. In my mind, though, things can change in an instant, whether you’re the highest paid person at your company or the lowest. Or, the world could be hit with a global pandemic, which throws everything out of whack.

Nothing is ever guaranteed. Nothing is ever going to be perfect. Isn’t partnership about weathering life’s storms together, finances included? I push him for more as he gets increasingly more uncomfortable with my line of questioning. 

“I think you can still work on [your finances] while with a partner,” I say, and ask where this way of thinking may have stemmed from. 

He shares that it mostly comes from watching his parents. “What I recall is my mom giving [my stepdad] a hard time for not being a decent enough provider,” Greg explains. “I could never be in a relationship with somebody that’s constantly disappointed with what [I] bring to the table financially.”

“Is there any possibility that their experience isn’t going to be yours?” I ask. “Is it a fear because of what you’ve seen, or because you’ve experienced it with a partner?”

“No, I haven’t experienced it… but I won’t allow myself to ever experience it,” Greg says. 

We go back and forth for a little over an hour. He holds steadfast to his view. I remain confident that this metric can’t be something that holds him, or anyone else, back from finding a partner (if that’s what their end goal is).

After a bit of research, I’m not sure if either of us is fully right or wrong. In 2019, a Pew Research study found both men and women earned more and were more financially sound in a committed relationship. Point in my corner.

On the other hand, money was found to be a leading cause of marital conflict in 2024, according to Forbes. And lower income couples have a greater risk of divorce due to money issues. Okay, point back to Greg. 

A 2022 piece from Business Insider says that millennials may delay marriage because of money more than older generations. But financial therapist Megan McCoy suggests that we may actually become wealthier if we get married sooner.

It seems to me that the right person would be open to adjusting their expectations for their partner’s financial situation. Or, for a time, they’d be happy to be the breadwinner until the person with debt can work through it for a more balanced partnership. 

“I am open to it. It’s just not a priority,” Greg says as he questions my argument. “I don’t spend a lot of time thinking about this. But thinking about it now, me not giving myself the opportunity to do this because of a reason that’s obtuse…”

He trails off, and we sit in silence for a few moments.  

“It’s fear, Nicolle, absolute fear,” Greg admits. “I mean, that’s fundamentally it, right? I don’t want to be a let-down.”

There it is.

To put it so plainly is to face the fact that dating from a place of fear simply doesn’t work, no matter what your worries are. Falling in love is one long trust exercise—there’s no guarantee that someone will, for instance, read your column when they say they will, much less treat all the vulnerable parts of you with the gentleness they deserve. 

I think this is worth exploring. Greg isn’t alone in his thinking, and I’m not 100 percent correct in my assessment that finances shouldn’t hold you back from dating. But like Greg mentions, actually taking the time to dissect your reasons for not pursuing relationships may help you figure out what are fear-based hangups and what are real, solid concerns.

If money was the only issue standing between my ex and me, I fully believe we could have made it work. But it wasn’t the real reason we didn’t last, and it won’t be the reason he doesn’t work out with someone else.

And, look, even if a long-term relationship was guaranteed to negatively impact your finances (it isn’t) and to take up more time and require more work than simply being alone (it is), how many people would still seek love? Many, I’d be willing to bet. After all, the rewards of love go far beyond the material. 

And that may be well worth facing your fears.

As for me, I’ve been continuing to go on dates and meet people through my matchmaker. Others have slid into my DMs through this column. Some haven’t worked out, some are upcoming, and one made me laugh the entire evening (but that’s for another time).

If you’re new to Unhinged, catch up on all the dating chats you’ve missed here and follow along at @monicles and @sandiegomag on Instagram to know when a new article drops each week.

Sign-up now for the Unhinged newsletter for exclusive content, Q&As with Nicolle, and subscriber-only meet-ups!

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The post Unhinged, A Dating Series: More Money, Fewer Problems? appeared first on San Diego Magazine.

I loved him and swore I’d marry him. After college, we moved from LA up to the Bay Area, where we began to pursue our respective careers. We talked about marriage, but I was, admittedly, not ready to settle down for the rest of my life. 

My memory is pretty spotty from that time, but I do know that we didn’t work out because of me. I was finally living on my own for the first time. A part of me wanted to explore this new freedom and figure out who I was before getting married. I pushed him away.

I think about him sometimes. I liked Chris pretty quickly, but he wasn’t someone that stood out in a room. He could be quiet, shy almost. He was cute in a nerdy kind of way. Safe. 

It wasn’t love at first sight, but I did feel something that I’ve only felt with a handful of men: intrigue, a need to know more about them long after they’ve left the room. Our conversation would flow from the start, we’d make each other laugh, and there’d be a hint of attraction. 

These types of interactions are rare for me, especially nowadays. But when they occur, I know that something special is happening. They almost always lead to that person becoming my boyfriend (though that’s not to say that every crush has turned into a relationship). 

I share this because I’ve been on four dates in the last two weeks, and I haven’t felt this same excitement with any of them. Save for a non-matchmaker-organized date that may have involved a white powdery substance (Unhinged subscribers can learn more in this week’s newsletter), they seem to have been decent guys, just not my decent dude.

It’s made me question myself, wonder if I’m being too picky. If that feeling I’ve had in the past isn’t as telling as it once was. I’m genuinely unsure if I’m not giving myself enough time to figure out who could be a potential match or if I really just haven’t found him yet. The only thing I can really bet on is that when I got that particular feeling before, I knew I could be completely myself. As a people-pleaser, this can be hard for me.

Here’s the thing, too. I know that butterflies aren’t real, that this type of hyperarousal is typically asking us to pay attention to something, often a red flag or at least a warning sign. I know that attraction can grow on you. I know that having the same values is more of a marker than both enjoying the same hobbies.

But what I don’t know is whether I can still have it all. Do I get to be so in love with and turned on by my partner while also feeling secure, confident, and supported in our relationship? 

What I’m learning, while dating at an older age, is that settling is a hard pill to swallow. And maybe that’s why some of us are having a hard time out there.

We’ve spent so much time reading books, listening to podcasts, building our careers, making and learning from mistakes, and healing our traumas that anything but AMAZING doesn’t seem worth it anymore. 

And that’s where I’m stuck. I don’t necessarily think this is a problem with finding someone who I could settle down with. I do think that there have been opportunities, but finding just anyone to be with has never been appealing to me. I don’t want companionship for companionship’s sake. I want someone who truly challenges me and complements my life. 

I’ve met men who made me feel safe… if a little bored. I’ve met some who made my heart rate speed up, despite being walking red flags. Some of my best guy friends are amazing, the kind of people that I’d happily set up with my girlfriends.

What I’m seeking, though, is a bit of all of it: safety and excitement, deep talks and belly laughs, heat and calm. And that’s a harder ask. Very kind, well-intentioned people sometimes ask how or why I’m single—can’t I find a man? 

What the question seems to miss is the distinction between a man and the man. Someone to love versus the love of my life.

Because if I’m not going to have the kind of romance that makes my heart jump when I see them in 30 years, then I don’t want it. Give me stability, trust, and kindness, of course. Sure. Obviously. But I’d like to also hold out for that all-encompassing, heart-pounding Notebook type of love.

What’s incredibly scary about this column, is that, for however long I do this, it may amount to nothing. No finale episode with a single rose. No hard launches on IG. But as my forever girl crush, Rihanna, once told Vanity Fair about finding a man: “I will wait forever if I have to … but that’s O.K.”

If you’re new to Unhinged, catch up on all the dating chats you’ve missed here and follow along at @monicles and @sandiegomag on Instagram to know when a new article drops each week.

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“I found your article kind of provoking, and I appreciated you writing it the way you did, because I was like, ‘Yeah, that’s exactly how it is,’” Lind says. “Like the thing about false starts and how it can be… It’s so exhausting.”

When I asked him if he’d be up to talking more with me about what dating has looked like for him, he readily agreed. 

Lind is both a professional photographer and a roadie for bands, which means he can be away from home for up to six or eight months at a time. Since the age of 20, he’d been chasing his dreams of becoming a video director (a title he now holds).  

“When I took my foot off the occupational gas pedal [at the age of 34], I had this whole big section of my life that I hadn’t even touched, this romantic side,” says Lind. “I was just so bad at speaking the female language.”

He tells me that, since then, he’s been working on himself through therapy and learning to understand what he wants in a relationship and with a partner. His answer for the latter is pretty simple: someone he can have a good time with, a spark that develops into a deeper connection.

But what struck me during our conversation were the slight contradictions in Lind’s words. He simultaneously declared that he was ready to date and emphasized that he didn’t want to be rushed into anything more serious.

“I don’t want to put any pressure on an early relationship by absolutely saying I want this or that,” Lind says. “Unwarranted pressures on first dates are hard enough. We’re both sweaty and nervous. Let’s chill. Can we have a conversation and see if we vibe and then go from there?” 

By “unwarranted pressures,” he means the big, life-stuff conversations: learning whether your date wants to get married or have a family, talking about how they view a future with their partner. As we chat, he says he feels pretty agnostic about the potential of having children. 

“I need to see the evidence. I need to feel true love before I can feel the idea of bringing a life into this world,” Lind says. “That’s a big responsibility to me, and I don’t take that lightly. I’m not just going to have a kid to have a kid. I would have to have somebody I love and trust in order to bring them into this world.”

He’s weary of these convos when they come up early on. To him, an overeagerness to talk about kids indicates that the other person might be willing to settle just so that they can have a child. I ask him whether that might be a false assumption.

Personally, I know I want children, but that doesn’t mean I’m ready to have a baby with the next willing Y chromosome just because we’re dating. 

“Right. Yeah, certainly. I think that’s very fair,” he replies. 

I’m sure Lind is not alone in his reluctance to discuss serious things early on. But what he sees as relationship-killing expectations might be valid questions that his dates are asking to determine if their hopes for the future align.

Lind, for his part, seems like a sincere guy who has taken steps to know himself better so that he can be a better man for his partner. I do think he’s looking for commitment and will work on being a good communicator once he’s in a relationship. But I can’t help but wonder if the “false starts” he’s experienced are, in part, a result of this subconscious mindset. 

And maybe understanding the way some may approach dates can help him and others put an end to that cycle. 

Being 40 factors into how I show up on dates. I’m much closer to understanding who I am and what I want my life to look like than when I was in my 20s. I’m not as willing to wait around to discuss the things that matter to me anymore, and I imagine that others like me feel the same. After all, the sooner we find our person—the right person, not just anyone—the quicker we are going to be able to achieve those dreams. 

It’s fine that Lind may not want to have those conversations on the first date. But that might mean that someone who is might not be a good fit for him—and who can blame them for wanting answers right away?

What do you think? Does Lind have a point? Does discussing your future desires early on add unnecessary pressure to the first few dates? Or could this way of thinking be hindering singles from moving past the dating stage into long-term relationships?

See you next week!

If you’re new to Unhinged, catch up on all the dating chats you’ve missed here and follow along at @monicles and @sandiegomag on Instagram to know when a new article drops each week.

Sign-up now for the Unhinged newsletter launching this April. Get exclusive content, Q&As with Nicolle, and subscriber-only meet-ups!

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The post Unhinged, A Dating Series: Under Pressure appeared first on San Diego Magazine.

But, after walking her to her car, he turned, grabbed her face, and kissed her. He was cute, so when he asked her out again, she decided to give him the benefit of the doubt. They met up at Fiesta Island with their dogs and chatted during a walk.

“I was asking him questions and he was giving me one-word answers,” says Mackenzie, 37. “So I decided that I was going to not ask him any more questions and just see how much effort he would put in. But he just basically interacted with his own dog.”

After lots of silence, Alex decided to leave. The date lasted 30 minutes.

“I was like, ‘Okay, he obviously feels like this is a bad date. He’s obviously not interested,’” Mackenzie says. “And then he texted me [two hours later] as if that was a normal date. [I’d thought] I was never going to hear from him again.” 

She was confused and understandably over his hot-and-cold approach. Two days later, she said goodbye to all dating apps. I don’t blame her. She’s not alone in feeling that sometimes men lack either the desire or the skills to meaningfully engage, especially when chatting on the apps.

In her column It’s a Pleasure, which focuses on sex, dating, and relationships, author Sophia Benoit offers advice to a reader who hopes to stop having dates with one-sided conversations.

“Not asking questions is, to me, a deal-breaker. Not because it’s impossible for someone to change their behavior, but because you shouldn’t have to walk a fellow adult through basic conversation tips,” she writes.

Finally, someone said it. I’ve struggled with this for years on dating apps, and I never understood it. I thought things might change when I started seeing men in their 40s, but  they have not. And the issue isn’t just anecdotal.

“Research shows that this lack-of-men-asking-questions problem is real, and it’s common, and frankly, it’s embarrassing for them!” Benoit says. “(To all of the 13 men who date women and who do ask questions on dates: This isn’t about you, but please send this article to any man friends you have.)”

So what’s going on here? Turns out there are tons of articles and forums dedicated to this very topic. Women on subreddits like r/Bumble, r/dating_advice, and r/OnlineDating have launched threads asking for an explanation. 

Quartz contributor Elizabeth Weingarten might have one: Social scripts for communication differ by gender, which can lead to confusion and conflict in heterosexual pairings. “In my experience, men who ask questions—the kind that show they’re actually interested in the answers—are rare and wonderful unicorns,” Weingarten writes.

Her sources, including dating experts, psychologists, couples, consultants, and entrepreneurs, confirmed that men have been taught to dominate the conversation as a way to “negotiate for status in the social hierarchy or to preserve independence,” she explains. Women, on the other hand, have learned to use conversations to determine if there’s a connection: “Do we have similar tastes, interests, values?” 

So, sure, sometimes a guy is just not that into you, or he’s distracted by other in-app convos. But it’s just as likely that he’s trying to impress. A man might reason that his date will want to get to know him only after he’s proved that he has the resources or experience to be a great boyfriend. Meanwhile, she’s dying for him to be inquisitive so she can tell if their personalities are even compatible.

In other words: Dudes, skip the peacocking. Relationships will progress faster and farther with genuine conversation. 

“Being curious about your partner helps you know more about them, which leads to the desire to know even more, which creates conversational interactions that lead to enduring intimacy,” writes Dr. Erin Leyba for Psychology Today, drawing from a study published in the Journal of Social and Clinical Psychology.

And that’s intimacy in all forms. Asking questions doesn’t just lead to deep, serious talks. It can also help dates relax and laugh together. You’ll have more fun and, well, better sex.

For what it’s worth, several men replied to the aforementioned Reddit threads pointing out that they’ve faced the same lack of questions from women on apps. Perhaps we’re all fatigued from the difficulties of the modern dating scene (and still getting our social sea legs after Covid). Maybe we could all use a little conversational practice.

Luckily, there are plenty of resources to help us talk to each other. Weingarten finishes her article with five tips for communicating more effectively. You can read them here. 

After all, it seems that the more questions you ask, the more likely you may find yourself enjoying a cold one in front of your potential soulmate.

If you came to the column this week to find out how it’s going with Ryan and Connor, updates are coming! I also worked with my matchmaker to refine my preferences for the kind of man I’d like to meet, so perhaps some more first dates are in my future. As always, happy dating and see you next week!

If you’re new to Unhinged, catch up on all the dating chats you’ve missed here and follow along at @monicles and @sandiegomag on Instagram to know when a new article drops each week.

Sign-up now for the Unhinged newsletter launching this April. Get exclusive content, Q&As with Nicolle, and subscriber-only meet-ups!

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The post Unhinged, A Dating Series: Ask Me Anything appeared first on San Diego Magazine.

And then, I looked up. Six-foot-three, wearing a flat-brimmed hat and large grin—my five-one self was suddenly glad that I became a rock climber during the pandemic. Within minutes we were chatting and flirting. His hand began to graze my lower back as he spoke. 

And then we kissed. 

Smooching in bars at 40 isn’t my idea of romance, but if you make it to the top of the Empire State Building, you don’t miss out on the view.

At the other end of the bar, in a fun twist, my ex John was shooting his own shot with multiple women. There are some days that seem more scripted than others. Maybe I really am living in a rom com—or at least a comedy. Most days the rom feels elusive.

Ryan got my number and texted me the next day, but I didn’t hear from him again until three days later, when I reached out. The Lion’s Share in downtown was throwing an anniversary party, so I asked him to be my plus-one.

He was wishy-washy about his answer up until the event started. He agreed to show up a little late. This was the first time something inside me wondered if he was the commitment type, but it was still early.

I got butterflies when he arrived. He was immediately affectionate, stroking my back and complimenting my outfit. We kissed on barstools in a dark corner later that night as we sipped on tequila sodas and beer.

As we chatted over the next couple of days, I let him know that I didn’t want to be the only one asking the other person to hang, but still, I invited him to watch the Super Bowl with my friends and me. He said he’d let me know. 

When he didn’t show and instead asked if I wanted to come by afterwards, I declined, feeling that sense women get when a guy only asks to hang late at night.

A few weeks after meeting Ryan, my matchmaker set up my first date with a pre-vetted person: Connor. He’s 44. A lawyer. He goes to therapy. He’s active and an avid traveler. He wants a family and loves pupusas (the food of my Salvadorian roots).

 On paper he seemed like a catch.

My matchmaker let me know we’d be meeting at Stone Brewing in Liberty Station and gave me his number the day-of. First dates are always a little nerve-wracking, but meeting a complete stranger (save for three mediocre photos and a quick bio) was a bit less intimidating.

When he walked up, my initial reaction was that he was attractive, though not exactly my type. But Connor surprised me. I didn’t feel the same butterflies as I did with Ryan and we didn’t have the same flirtatious banter, but we had more meaningful conversations.

Connor showed up as a man—meaning, he didn’t seem like many of the young guys I had dated before. He spoke with self-awareness, shared his points of view while listening to mine, and asked me enough questions that I felt like it was a conversation and not a one-sided interview. 

We also shared personal family stories. I opened up about private things that I would never share on a first date—stuff I’d usually withhold until we’re closer to relationship status. He told me about his family dynamics. Conversations like this could be uncomfortable for some this early on, but I appreciated that he laid it out for me and allowed me to decide what to do with it. There was no hiding for either of us.

After the date ended, he walked me to my car, we hugged, and I went home. I don’t think my insides were doing somersaults, but I do think meeting someone who has worked on themselves, knows their value, and possesses emotional intelligence is becoming harder to find these days—at least in my own dating life. It was refreshing.

He texted me before we went to bed, thanking me for hanging out. He also brought up an awkward moment that had occurred during the date and addressed it so that it didn’t linger longer than that evening. 

Connor asked me to hang out again. Our next date is planned for tonight. He picked two places ahead of time—neither is in our neighborhoods (he had to do his research). It’s this little bit of effort that, in my convos with others, really makes a difference nowadays.

If I’m being honest, though, my gut is sending up a few warning signs with Ryan while my emotions need to catch up to my brain with Connor. I’m used to the Ryans of the world and see glimpses of my ex in him already. It’s easy to dive in head-first when the attraction is front and center, but I know that I don’t want to do the heavy-lifting while I date anymore.

With Connor, I’d normally be quick to assume it’s not a match. Not because we didn’t have a lot in common, but because the immediate attraction was missing. It’s not a novel concept to me that you can fall for someone’s character before falling for their looks. Some of my exes started as friends. But it’s sincerely hard to always put it into practice—especially when you feel like time isn’t on your side anymore (hello, 40).

Part of writing this column is to take accountability for how I date, but to also be willing to make the kinds of decisions that can finally change the course of my previous love stories. So with that, will I be able to cut things off with Ryan if he can’t match my dating efforts? Can I give Connor the time needed for something more to develop?

Time will tell how each plays out, so I guess you’ll have to come back next week to see how things are going. I’m curious to find out myself.

If you’re new to Unhinged, catch up on all the dating chats you’ve missed here and follow along at @monicles and @sandiegomag on Instagram to know when a new article drops each week.

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The post Unhinged, A Dating Series: A Tale of Two Men appeared first on San Diego Magazine.

We’re four weeks into this series, and I have read every single comment and every single DM. It’s been so cool to see that I’m not alone in not knowing what the hell I’m doing when it comes to romance—and I also want you to know that you are being seen, too; that we are all in this together.

Occasionally, I’ll get some feedback that’s not exactly constructive—or kind—and, for a moment, I wonder why I’m doing this. And then a message like this comes in and reminds me of the reason:

“As a longtime single woman nearing 40, it’s incredibly validating to hear a perspective on dating that is not from the vantage point of: ‘I was single like you once but I found love, and now I hold the SECRET to finding it.’ I think there’s a lot of content out there aimed at single women telling us what we’re doing wrong, so I’m always looking for content that empowers us in our dating process. I’m looking forward to reading the rest of your series!” –Jeannine B., 39

I don’t have all the answers, but that’s the whole point of this series. I’m right there with you, questioning everything and wondering if it’s me, the system, or a little of both. I’m hoping that by being forced to self-reflect each week, I (we?) can begin to understand how to date in a way that feels intentional, fun, and rewarding.

Besides, there are plenty of other incredible voices, experts, and content creators in this space with in-depth knowledge and years of research that are giving great advice—people like matchmaker and SD local Sophy Singer, who has spent 14 years finding matches for singles.

For this week’s installment of Unhinged, I tapped Singer to answer some looming questions I had regarding today’s dating culture. Here’s what she had to say: 

Are there any questions that can help people get a deeper sense of someone other than the typical first date lists? 

“What are your top values? What’s most important to you in life?”

I think a really cool question to ask—because I ask this when I screen people for matches—is, I ask them about their past relationship. “What was your takeaway from that relationship? What did you learn?” You want to know how self-aware they are. Are they pointing the finger toward the other person only?

Is there anything you’d steer clear of as topics for a first date? Like if someone’s a single parent, or if religion is very important to them, when should you talk about these things? 

If you asked me [two-and-a-half] years ago, I would have said don’t talk about politics. Don’t talk about religion. Don’t talk about sensitive topics.

Not anymore. Talking about sensitive family topics—I didn’t welcome that because I used to be very ashamed of my own family history. My parents divorced and my father went to jail. And I was like, “I don’t want somebody to ask me that, and I don’t want to ask them. I don’t want to get uncomfortable. I want things to be light and fun.” And of course they can be light and fun. That doesn’t mean you can’t have fun on a first date. 

Let’s say, for example, you’re on a date and religion is important, right? You bring it out and talk about it and you can say, “Hey, the reason why I have this curiosity is because I have this value around this.” [Or] you can just say, “Actually, I want to talk about this stuff because I have such a curiosity on where you fall here and what value this is for you.”

But, also, be aware that trauma bonding is not a great idea off the bat. I would say it’d be good to have self-awareness. [You can say], “You know, I feel like this is a little edgy and maybe going a little too deep, so please let me know if you are open to me asking and please know that you definitely don’t have to answer.” You can always just create a little bit of softness around that.

After a first date, how can you tell when your gut is saying “This person isn’t the right match for you,” or whether past fears, traumas, attachment styles, or experiences are affecting your mindset?

Well, first thing is, how aware are you of yourself and the parts of you that pop up? The fears and blocks. 

If you’re more self-aware, you have a better idea [of how to say,] “Oh, I’m having this reaction. Oh, this must be based on my past. I’m reacting because of this.” Or, “Oh, this is something I don’t like about myself. And that’s why I’m annoyed by this other person. Maybe I need to work on that.”

[Going on a] second date should always be the default, unless it’s obvious—like if they show up and they’re just super off-putting. But maybe they weren’t opening up. Maybe they’re nervous […] because sometimes people really are nervous on a first date. So I think a second date should be the default [to determine if you’re a match]. 

What do you do when the other person isn’t being intentional about dating you? For example, some have said things like, “Oh, I just don’t plan dates,” and only ask to hang out last-minute when they have nothing else going on.

I think it’s frustrating because it makes us feel like seeing you and spending time with you and the relationship is not really enough of a priority to plan ahead. Sometimes it indicates, for me personally, less of a respect of my time and my energy. That’s not necessarily their intention or where they’re coming from, but that’s how it makes us feel. 

If you want to depend on other people to determine your experience, great. You could sit around and just decide that that’s what dating is these days. Some people think that’s easier. I think it’s harder. 

So [have a] conversation: “I [appreciate] making plans ahead of time […] with somebody that I’m getting to know and making sure that that happens in a little bit more of an intentional way. I don’t have to have every single date planned ahead of time, but I do value having that be a part of dating somebody.” 

Are we going to just dismiss [someone] and let this potential connection die immediately, or are we going to reveal our needs and give the other person an opportunity to step up to meet you there? Because if we don’t let them know where you need to be met, how can someone have the chance to do that? They can’t read your mind, and everybody comes to dating from different places.

If you’re new here, catch up on all the dating chats you’ve missed here and follow along at @monicles and @sandiegomag on Instagram to know when a new article drops each Friday. Have questions you want answered in the column? Email Nicolle at [email protected] with topics you’d like to see covered.

Sign-up now for the Unhinged newsletter launching this April. Get exclusive content, Q&As with Nicolle, and subscriber-only meet-ups!

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