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Unhinged, A Dating Series: Better First Dates

Matchmaker Sophy Singer shares her advice for asking the right questions and being honest about your needs
Sophy Singer of Sophy Love San Diego

In Unhinged, San Diego local and SDM editor Nicolle Monico shares her experiences dating in the city while hopefully finding love in the process

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.

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By Nicolle Monico

Nicolle Monico is an award-winning writer and the managing digital editor for San Diego Magazine with more than 15 years of experience in media including Outside Run, JustLuxe and The San Francisco Chronicle.

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