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Unhinged, A Dating Series: 7 Lessons Learned While Dating in SD

Looking back at the past eight months, columnist Natalie Cooper details her experience with searching for love in the city
San Diego Dating advice column Unhinged featuring Natalie Cooper's final column titled "7 Things I Learned While Dating in SD"

One year ago, I ended a relationship that I thought would be my forever. It’s strange to think in those terms, the idea of forever and all that might have happened between us, and all that will never happen now. But to see how much can change and be accomplished in only 365 days, I’m re-writing my concepts of time. I’m imbuing my future with a new kind of depth and richness I never thought possible, and I’m looking forward to what comes next. 

I am writing this over the sparkling pool at my new girlfriend’s apartment. It’s a cool 80 degrees in mid-October. I’m in my bathing suit, grateful to be soaking up the last few drops of San Diego’s wildly extended summer. The person I was last year at this time no longer exists. The ideas I had for my future back then are no longer relevant. In that girl’s place is a person that I am still learning, but who I respect and admire. She’s worked hard, learned how to pick herself up, faced difficult truths, she’s been brave. And so, it’s time to once again embrace change, and bring this column to an end.

San Diego couple on a date at Belmont Park

Unhinged has been the perfect sandbox to play in, in a time when I needed a safe space, a place to put my thoughts, to connect with people going through their own struggles with love in San Diego. I’m unbelievably grateful to Nicolle for passing the baton, and giving me the opportunity to share my journey, my mistakes, and my musings with you. Dating is messy, vulnerable and exhilarating. It asks you to navigate your own heart and to be deeply curious about other people.

Getting out into the scene again in my mid 30s was terrifying. I had never used dating apps, and I didn’t know how to present myself in this late-stage era of their adoption. Would I be marketable among all of these savvy users? Would I come off as some post-divorce, mid-millennial luddite? At the end of these past eight months, I’ve discovered some truths about dating and wanted to share them below.

Dating in Your 30s is Fun

I found people to be far more compassionate than I expected, and that dating in my 30s is actually a lot more satisfying than dating in my 20s. People are showing up with fascinating stories and lived experiences. They’ve made mistakes and learned from them, and have room for my story and my past mistakes, too. What matters is showing up clear-eyed about the future. I also feel more resilient about dates not working out, or needing constant communication with dates that do. My confidence in myself is bolstering my bravery to put myself out there and risk being bruised. 

Not All Things That Shine Are Bright

I learned how to recognize and call out some of my old patterns, moving past the “shiny” people that at first might have seemed exciting, and challenging myself to look instead for signs of maturity and intentionality from would-be matches. The old me would have been drawn to people who have some flashy story or passion, but as I’ve gotten clear on my patterns, I know that those people make me feel competitive, and are often masking deeper insecurities. Now I’m looking for people who satisfy my core needs and don’t put me on edge.

Red Flag Meters Sometimes Need Re-Tuning

I explored vetting my red flag meter against new circumstances, asking myself to understand the core of my discomfort versus just the person’s behavior on the surface. For instance, I find myself wrestling with my aversion to sports fans. Is it the sports that are the problem? Or am I just not attracted to reckless spending on merch, games and beer? Trusting your gut instincts, reflecting on your dating history, and communicating clearly with your partner about your boundaries can head off troubles before they begin.

Today’s Dater Can Benefit From Centuries-Old Traditions

First date tension? Swiping burnout? Perhaps seeking advice from a seasoned matchmaker could be the next step in finding lasting love. I talked to Sophy Singer of Sophy Love matchmaking about the benefits of seeing a matchmaker who looks at you and your relationship goals from a holistic standpoint, identifying patterns that are stopping you from finding a fulfilling, well-matched relationship. A matchmaker can help you focus on what it is you really want, show up authentically to first dates, and encourage you to move past surface level dealbreakers or checklists like height or education level.

Leaning on Friendships is Essential

I’ve found that sometimes getting out of my own head, and asking other people for advice can be the key to moving forward past my own stumbling blocks or an issue I’m having in my love life. I’ve allowed myself to become very vulnerable with friends that I trust and whose relationships I respect. I’ve been surprised with the ways they have shown up, thinking about my situation with honesty and focus as I’ve moved through heartbreak to rebuilding to new relationships. It’s helped center my friends in my life in a way I’ve never done before, and now I feel that I have an extended family who loves and supports me as I am.

Despite Its Stereotype, San Diego Can Be a Great Place to Date

The great news is that San Diego is an incredible place to date. The city is thriving with people from all over the world, with endless opportunities to find love. We’ve got a fascinating cultural scene, bars and restaurants galore, hiking trails, beaches, parks. Even dating on a budget is easy, so you never have to cross your own boundaries (even financially) to see if that new person could be your person. 

And if you’re sick of the apps, exploring the city alone could be your next opportunity to meet the love of your life.

There is Hope After Heartbreak

Although I have met someone new, I have no idea what the future holds. All I know is that I’m hopeful, and for perhaps the first time in my life, less afraid of the unknown. I now know what I’m capable of, and that if you lead with an open heart, the world can open to you. I also know that I’ve met someone who motivates me to be my best self. She leads by example. She inspires me every day, and I’m excited to see what we can build side by side.

We are all a perpetual work in progress. You or I will never be perfect, and we will never find the perfect match. But love is more interesting than perfection. I’m open to the journey; thanks for walking a small leg of it with me.


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

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