Dating in Philly After 30: Ugh.

What’s it like to reenter the dating pool in your early 30s … after a divorce … when the last time you were single, Facebook was a print product? A tale of iguanas, E-A-G-L-E-S chants, and one really big glass of panic pinot grigio.


Illustration by Tim Parker

I was a little nervous. Maybe more than a little nervous. It had, after all, been a solid 10 years since I’d been on a first date, and if my memory served me correctly, I wasn’t all that good at them.

But I relaxed a little when he finally walked through the door of Johnny Brenda’s. Tall, well-dressed, seriously great smile — this was going to be just fine. We had met a few days before while waiting for our tables at brunch, and he was so charming that I agreed to follow-up drinks before remembering that I wasn’t ready to date.

“I’m so sorry I’m late. I was waiting on a friend,” he explained as he pulled out a chair and put his book on the table.

“No worries. Everything okay?”

“Yeah, he’s just going to meet us here.”

“Oh? Um, okay, sure.” Even I knew this wasn’t the way first dates were supposed to progress.

“I can’t wait for you to meet him. He’s my best friend, actually. In fact, you might already know him.”

“Maybe … ” I cursed the city for being so small and peeked at my watch. If I left now, I’d make it home in time for Jeopardy. Mr. Trebek would never invite a third wheel to our standing 7 p.m. appointment.

“His name is Jesus Christ.”

It was then that I realized the book on the table was a Bible. And that my overly friendly brunch buddy was a missionary. And that this wasn’t so much a date as it was a recruitment session.

I excused myself for a minute, ordered a very large glass of wine from the back bar, and headed to the bathroom.

I’ve never been one to make plans, so I didn’t really know what Friday night was going to look like in my 30s. If I’m being honest, I guess I didn’t expect to be sitting down to dinner in Ardmore with my adoring husband and 2.5 children. No matter how generous the math, that scenario didn’t add up. But at the same time, I didn’t think I’d be drinking pinot grigio on the toilet, either.

Even for me, this felt like a setback.

WITH THE POSSIBLE exception of reality stars, I don’t think anyone who gets married expects to get divorced. I certainly didn’t. Because here’s the thing about divorce that Eat, Pray, Love conveniently forgot to mention while flying off the shelves: Divorce sucks.

Maybe it’s a journey of self-discovery and enlightenment when you have a sweet book deal, a massive expense account, and reservations at a luxury ashram in India. But when you’re working with a freelance magazine contract, a Target gift card and a one-bedroom in South Philly, divorce simply sucks. And it especially sucks when you’re 30.

Not that there’s ever a good time to drop the D-bomb on your life. I imagine it’s difficult at any age, and I don’t envy people who have to navigate the process with children. It was painful enough giving up custody of my cats, and those little bastards spent their few waking hours plotting to kill me.

But my timing did seem to be uniquely bad.

For one, a lot had changed about dating in the decade I spent on the sidelines. The last time I was single, I think Facebook was a print product, and my Nokia flip phone was top-of-the-line. I had reasonable AOL Instant Messenger game back in college, but nothing could have prepared me for the way people who want to undress each other communicate in 2015 — which is to say constantly, indiscriminately and, from what I can tell, in code. While “sure” felt like an unsatisfying answer to a question in 2004, at least it was a correctly spelled word in the English language and not, say, a thumbs-up emoji. There is only one finger I want to answer the vague, noncommittal thumbs-up emoji with, and Apple forgot to include it.

After about 48 hours on OkCupid, I decided I’d rather die alone than next to someone who claims that he’s “all about living in the moment.” It took me even less time to give up on Tinder, mostly because I couldn’t figure out how to download the app. And while I’m still not sure what Snapchat is, I do know that if you toss your phone in the Delaware, it magically stops both snapping and chatting.

But suppose you do know how to swipe right with some finesse. Let’s say you don’t consider getting texted five times in one day to be grounds for a restraining order. (Although for the record, it definitely is unless you’re Dave Matthews wondering what kind of ice cream to pick up on the way over.) Even so, dating is tough in your 30s — and it’s especially tough in Philadelphia.

In New York, seemingly everyone is single. Whether you’re 20 or 50, there’s no shortage of people who are out and about, casually dating their way through life. And this is great, until you realize why: They exist in a perpetual state of looking for the next best thing, and the next best thing is 10 minutes behind you. The same goes for L.A., except in L.A. she’s only five minutes away, and that bitch can surf.

Philadelphians, however, are a realistic bunch. It’s not that we settle, but we know what we like and we know where we stand. By 30 or so, most of us have either found The One or taken a good look around and decided that all things considered, This One was a pretty good deal.

True, there are some perfectly dateable 30-somethings in this city, including one lovely man whose only real mistake was marrying a writer who would sooner drink wine in the bathroom than make eye contact with a Bible. But for the most part, it looks like your sock drawer on laundry day — lost souls and career loners who never quite mastered the art of pairing up and holding on through the spin cycle.

A couple months after my Johnny Brenda’s non-date, I found myself out to dinner with an interesting gentleman who couldn’t keep his 9/11 conspiracy theories — and, worse, his dessert fork — to himself. Then there was the accountant, who seemed promising enough before he whipped out an E-A-G-L-E-S chant during the Nutcracker intermission. How many iguanas are too many iguanas to own and still be considered dateable? Thanks to a traumatizing morning-after in West Philly, I now have an answer to that: three.

Not that I really had room to talk. Since my divorce, I had been bringing home even more shih tzus than usual. And as it turns out, there’s very little difference between a newly rescued shelter dog and a newly rescued boyfriend: They both look at you adoringly for the first couple weeks as they hang on your every word. Soon they get comfortable and start putting their dirty feet on your couch. A few months in, they’re stealing your french fries, snapping at your sister and trying to hump your friends.

Same progression, slightly different game, far cheaper Christmas credit-card bills.

AT SOME POINT, I realized that the problem could quite possibly — maybe even probably — be me. And so shortly after attempting to date, I listened to my therapist (a.k.a. a poster of Joan Rivers) and decided to take a break to work on my own life. I got back on my yoga mat, I called up old friends, I bought a juicer, like a good divorcée. I even reread Eat, Pray, Love, just in case I missed some hidden nugget of wisdom the first time around.

What I found may or may not be surprising, depending on how many times you’ve flirted with your own version of rock bottom. Personally, I almost got Lisa Loeb lyrics tattooed on my lower back last year. So please, forgive me if I come off as preachy, but I believe I’ve earned this particular soapbox.

First, I missed absolutely nothing in Eat, Pray, Love. The moral of the story stands: Divorce rich, marry a Brazilian, get richer, and you, too, will be happy. If you didn’t already know that, you never stood a chance in Philadelphia anyway.

Secondly, the problem wasn’t me. But I, well, I was me. Very, very much me, for the first time in my dating career.

I’m no prize. I’m messy, I’m insecure, I’m still upset about the Gilmore Girls finale. I have criminally bad taste in music and an unfortunate appetite for greener grass. Having my cake has never been enough. I want to eat it, too, and then I want to smear it on the walls and stay up all night reading UFO message boards while regretting the cake.

Would you rush to introduce me to your parents? No. Was I an easier sell in my 20s? Definitely. But I wasn’t exactly a finished product, either. I’m still not today, but I’m a hell of a lot closer to what I’m advertising, and I’ve got a pretty good idea of what I’m looking for.

The unfortunate truth is that, yes, the Philadelphia dating pool thins out in your 30s. And yes, you will go on a lot of disastrous first dates with people even stranger than yourself.

But the good news is that you won’t go on many disastrous second dates, and you’ll almost never be blindsided during the third. That’s the upside of being a little older, of knowing how many iguanas you need to get through this life and how many iguanas you absolutely can’t wake up next to.

I’ll leave the last word to Buddy Christ, who actually turned out to be a rather lovely dinner companion. “You know, you shouldn’t be so worried,” he told me. “You can always just DVR Jeopardy.”

Published as “Feeling Dated in Philly” in the October 2015 issue of Philadelphia magazine.