On Seeing People I Went To High School With On The Dating Apps

Before I officially changed my location on Hinge to the town I grew up in, I thought:

Maybe I’m just meant to be single?

The idea of selecting Rhinebeck, not Manhattan, not Brooklyn, went against all the ego-based barriers I’d built 20 years prior.

When I left high school, I was leaving. Capital L, leaving. The summer before my senior year, I’d done a summer program at Cornell University. You spent six weeks living in the dorms and taking two college classes. My face was red with tears when my mom pulled away, but I was an absolute ball of pride and excitement when she came to pick me up at the conclusion of the program. I’d entered into a space where no one knew who I was. I was surrounded by people just like me — hell bent on getting into the best university possible, so much so they elected to spend six weeks of one of their last summers at home at one of the top schools in the country.

When I entered senior year, it felt like nothing. I’d already taken college classes, I knew I could then handle my freshman year classes. I’d hang with friends and do my school work, but I was beyond all this.

I wore my hunger and eagerness to leave like a badge of honor. I suddenly had something that made me feel so much better than all of my peers. Whereas the year before, I felt filled with shame that I didn’t go to prom. This year, I could write it off more easily as something I was just…above. Something for folks not ready and able and willing to take their life in a legitimate direction.

(Are you cringing just yet?)

The armor just grew from there: I’d go to a university no one else was going to, I’d move to cities far away and pursue elite positions. I’d never come back. Moving back or staying around were for more small minded individuals. Folks who didn’t have as much on the horizon.

So, post-pandemic, when it really settled that I wanted, I freaking wanted to make my hometown home again, it butted up against all I’d built to bury the shy, never asked out girl I was running so desperately from.

Maybe I wasn’t popular but I’d built an academic record and career that would matter so much more. For years I relished in watching those I’d been so very jealous of growing up — the ones who always had a boyfriend or somehow knew exactly how to dress or who felt so comfortable in gym class — succumb to positions as local teachers or police officers. Something equally…regular.

That whole house of cards I’d built to prop up my own sense of self didn’t have a leg to stand on if I was coming back. It also, without a doubt, played a role in all the time I spent telling myself I wanted to be in New York City, I wanted to live in a city. Did I ever want that?

When I finally said to myself, “I can’t do this anymore,” it wasn’t just about the location. It was about the way I was dating in general. It felt less rooted in a desire to actually build a life with someone and more an attempt to squash something I was feeling. To run from what I couldn’t bear to be true about myself.

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Changing my location and beginning to swipe was a real rip the bandaid off moment. I was and wasn’t ready. I still recall the first photo I saw of someone I knew I went to school with. It felt weird to be in the same “space” with a person I never thought I’d share the same space with. I swiped left, and then another appeared. This one hit a little closer to home. We’d been in the same grade. I felt more shame when it came to him knowing I was there. To him knowing I wanted this thing — romance, love, a relationship. This thing I’d worked hard to make it appear like I didn’t want as a teenager. I swiped left again.

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After those two, that was it. The algorithm then somehow only brought me to individuals within a 30 mile distance, none of which I recognized from growing up.

There wasn’t some pinnacle moment within it all where I dissolved all that I’d felt before. All I’d built up. I still tend to change grocery aisles when I spot someone from my class I’d rather not talk to. My 20 year high school reunion this past summer, despite having the company of my husband, still brought me back to all those feelings. I could handle an hour of small talk and then we had to leave.

Every other day or so, I take my dogs to the fields behind my high school to run around. Recently, when we pulled into the parking lot, there was a big sign up affixed to the sports field fencing that read, “Spring Fling!” complete with a QR to get all the details.

I felt a lump form in the back of my throat. I let out an “Ugh,” only audible to the dogs, and turned the car around in a parking spot facing the opposite direction.

I found it curious I still felt that way. That such a sign would still conjure such a reaction. It’s fascinating to me what we struggle to leave behind, or fight to not know about ourselves. That 15/16 year old still needs my help. Theoretically I want to help her, but it requires intimately revisiting all that was felt and not felt. Apparently it doesn’t matter I have a hot husband (he really is so gorgeous) and a beautiful home with two dogs that I love. It still hurts that I didn’t go to prom.

And yet there’s a beauty to that. A simplicity. How very human of me. These days (for myself, and my clients), I’m more about being with and acknowledging, versus resolving. What would it look like to resolve this for me? What I thought would resolve it, didn’t.

So perhaps, it’s a matter of simply spending time with her. Bringing her sweet, shy face to mind. Letting her grieve that which she didn’t get and the career and accolades she chased to not be enough. We’ll see where we go from there.

If you like this piece you might also enjoy:

On not getting asked to the dance, and how it shows up in your love life.

The unique struggles overachievers face in dating and relationships.