I Had My First Date at 28

As featured on: The Cut

At the beginning of 2014, the relationship I thought would lead to marriage came to an end. For the first time in almost seven years, I was alone. I knew breaking up was the right thing to do, but it was still terrifying. How would I ever find love again, another partner, another best friend? How would I start all over again? These are questions most newly single people ask themselves, but my case was a little different: At that point, I was 28 and had never been on a true date.

Not one. While my relationship had included many “date nights” we met like most college students, drunk at a bar. After that we “met up” or “hung out,” often with other people, but never on a date date. The same had been true of other guys I liked in college. I’d attempt to “casually” run into them at a party or bar, down enough liquid courage to talk to them, and then hope things would work out. Back in high school, I was too shy to even consider the concept of dating, let alone engaging with the opposite sex. Time passed, and suddenly I was two years away from 30, the age by which I had planned to be married going on kids. Those were things I still wanted, eventually, but I had no idea how to begin.

I suspected, though, that it had something to do with apps. I downloaded the ones I’d heard of — Tinder and Hinge — set up quick profiles, and got to swiping. It didn’t take long: A week later, I was on my way to my first first date.

He suggested an after-work drink at a cheesy bar in midtown, a spot I would never have suggested for a post-work drink, let alone a date. But I wanted to stay open, so I went along with it. When the day came, a throw-away Wednesday, I wasn’t all that nervous, but I wasn’t all that excited, either; his profile was as vanilla as his choice of bars. But I went because I felt had to be doing something. I wasn’t going to meet my next someone hanging out on my couch with Friday Night Lights.

He was waiting outside when I got there, and I spotted him before he saw me. I knew instantly; I could see it in his hunched figure and timid body language. Not a match. We grabbed a spot at the bar and ordered a drink. After the typical where-do-you-live-and-what-do-you-do conversation, he asked about my astrological sign. Finally something interesting.

“I’m a Scorpio,” I said.

He immediately got to Googling. I was a little dismayed that we were already using Google to make conversation, but I went with it. He found a site that listed the pros and cons of each sign and zeroed in on lowlights: jealous, controlling, vindictive.

He seemed horrified. “Are you really like this?!” he asked.

Tinder had set me up with the world’s blandest man. And yet somehow I found myself trying to make a case for my character. Yes, I said, I did exhibit some of the negative Scorpio traits, but I also reflected many of the positive. Shortly thereafter we said our good-byes, went our separate ways, and, thankfully, never spoke again.

Despite the inauspicious start, I wasn’t too upset. The whole thing felt like an experiment in my new life. I never expected it to be easy. I moved on and scheduled a few more dates.

Some were coffees. Some were drinks. Some were walks on the High Line. None of them were great. No one ghosted or said anything horrible; the chemistry was just off. Nice people, but not for me. It was jarring to connect with someone online and then having nothing to say to them in person. Some of them were hilarious via text but confusingly shy when we met; others seemed sweet and kind online but self-involved in real life. It was tiring, sometimes even maddening. No matter what the algorithms said, or how people looked online, there was no predicting chemistry. Eventually, I grew so frustrated that I just gave up, and deleted the apps from my phone.

On the day I turned 30, I moved back to Brooklyn, something I’d wanted to do since my breakup almost two years earlier. My new apartment was not far away from where I grew up, and it felt like coming home. I set up my kitchen, I chose paint colors for the first time, I filled the fireplace with candles, I went to the farmers’ market, I found the neighborhood’s best weekend brunch spot, I started a regular yoga practice, I threw dinner parties. I started to live the way I wanted to live, more so than ever before. In all areas but one.

I had started to explore meeting people in person. I reached out to guys I’d had crushes on in the past to see if they wanted to meet up (they did). I met people at holiday parties, in coffee shops, on the subway. This was better than the apps, because the chemistry was clearer, but it still wasn’t good, and most of the fault was mine. The difficulty of starting over, and the ever-present fear of ending up alone, led me to overlook all sorts of red flags. So he lived on the other side of the country; perhaps I could move. So he had a gambling problem; he’s free to do what he wants with his money, isn’t he?

Their values went completely against mine and yet I ignored them all, for fear of never meeting anyone else. In doing so, I tolerated a hell of a lot of bad behavior. Ghosting. Cheating. Not confirming plans until the very last second. Excessive drinking. This went on for two years, and then I hit my breaking point.

Last fall, I was seeing a guy I liked a lot, but who told me from the start that he didn’t want to be exclusive. We dated for a few months, but I wanted something more. I told him so, hoping there was a slight chance he’d changed his mind. He hadn’t. He still wanted to be dating multiple people. That wasn’t right for me, so I ended it. But I couldn’t help but admire that, at least, he was clear about his priorities. And I couldn’t help but wonder what mine were.

Over Thanksgiving, I hunkered down with a pen and paper to attempt to honestly answer that question for myself. Why was I pursuing people that weren’t interested in the partnership I wanted? What exactly was the partnership I wanted? In every other area of my life, if I wanted something, I pursued it with intention, clarity, and determination. In my career, my friendships, dinner reservations, the impossible-to-find Brooklyn apartment filled with natural light for God’s sake. So why not in my love life?

I began to see that I had focused so much on making myself attractive to men, in the hope that someone would choose me, that I lost all sense of who and what I wanted. I had been afraid to want the kind of man who was deserving of my love, affection, and commitment. To want the man who had as much to give as I did. The scariness of starting over, the fear of never finding my partner, had made me settle over and over again.

A week later, finally clear about my own priorities, I had my first good date. Drinks and dinner with a lovely man in the West Village. He was kind and sweet, and the conversation was better than I’d had on a date in years. I felt myself opening up, sharing my wants, desires, and struggles like never before. I felt free. I was starting over yet again, but this time was different. I knew exactly what I was after.

This article was originally published on The Cut.