Dating is never easy—but when you came of age decades before the internet was a thing and you’re dipping into online dating, it can be terrifying. So suffice it to say when I found myself divorced and suddenly single at midlife in the modern age, I was a little weirded out.
When I first created an online dating profile, my now ex-husband and I had filed the divorce paperwork and were just waiting for it to be official. Because we live in New York City, we were still living in the same house, amicably hatching out arrangements for friends to buy the place.
So I sat at our kitchen table, the one we designed together and had custom-built, and there—with what felt like one foot in my past and one in my future—uploaded photos and filled out the little boxes on a dating website, answering questions about who I was and what I was looking for in a man.
At the time, I thought it couldn’t get any stranger than that.
Boy, was I wrong.
Then there was the guy who spent the first 30 minutes of our date crying over his ex-wife.
Once I actually started going out with people I met online, here’s what I encountered: The guy who spent the first 20 minutes of our date screaming into his cell phone at his ex-wife. The one who spent the first 30 minutes crying over his ex-wife. The one who thought he could and should hide his Tourette’s from me. (Spoiler alert: He couldn’t.) The man on Tinder who looked like an underwear model, claimed to be a doctor visiting for a conference, and offered to leave a room key for me at the front desk of his luxury hotel. (Um, no thanks … ?) And the one who explained in great detail why, every day of his adult life, he has only eaten plain spaghetti for dinner.
After a month of this I realized I was going to need some help.
Listening to My Dating Whisperers
So I met my friend Emily for drinks. Emily had been single the whole 15 years that I had been married and had only recently gotten engaged.
‘You need to wait six dates minimum before you have sex so that the guy takes you seriously,’ my friend said.
“You’re doing it all wrong,” she said. “First, you can only sleep with the ones you don’t want to keep. Otherwise, you need to wait six dates minimum before you have sex so that the guy takes you seriously.”
In that moment, it didn’t look like I would ever get to six dates with anyone. “At that rate, I may never have sex again,” I told her, gulping down my wine.
“Oh, no,” she smiled. “Dating isn’t really about sex. It’s about marriage. If you want sex, you should really get a buddy—but it has to be someone you would never end up with. Purely recreational.”
I was dumbfounded. Could this be right?
Then my friend Sally, a fellow writer who had 20-plus years of dating in the big city under her belt, decided it was her turn to set me on the right path.
‘Whatever you do: Don’t believe it when it seems like magic on the first date,’ another friend told me.
“Whatever you do: Don’t believe it when it seems like magic on the first date. If you feel fireworks, it’s because the guy wants it to seem like fireworks. Fireworks are a warning sign. Real connections that aren’t just about sex take time.”
“You should also give someone a couple dates,” she added, “before you write them off. Even if the first date is meh.”
Well, that didn’t seem terribly romantic—after all, some sparks really are sparks, right? I didn’t want to believe that my happily-ever-after could start with anything less than sparky.
Making My Love List
Next up for advice: My friend Sonya, a professional psychologist, marriage counselor, and sex therapist. We were just meeting for lunch, but I expected her advice would come with at least a little professional edge.
“People are going to offer you a lot of things,” she said, suggesting that I make a list of my “five must-haves” and “three deal-breakers” and using those to sort through the noise on Tinder and OK Cupid. She cited a study that said that the biggest problem people have in dating is too many options. If you stick to what you’re looking for, you’re much more likely to find it, she explained.
The biggest problem most people have dating online is too many options.
So, determined to be a very focused dating Goldilocks, I made my list … in the notes app on my phone, of course, so I could refer back to it when I was looking at profiles.
My wish list was longer than she suggested, and it covered everything from ethics (#7: Honest, loyal, decisive, and a good communicator) to personality (#11: Is turned on, rather than intimidated, by my intensity and directness; #16: Calls me on my shit and expects me to call him on his; and the critical #3 Makes me laugh).
The deal-breakers were more about intentions (#1: No players: Is ready for something serious when he meets the right woman) but also included some, well, conventional no-thank-you’s (#4: No repression: Knows what he likes and what he’s doing in bed. Is comfortable in his own skin.)
I didn’t care so much if people were divorced or widowed or had always been single, and I steered clear of putting limits on what sort of careers they held or lifestyles they engaged in. While my divorce had given me an almost manic energy that made working out feel, for the first time in my life, like a near daily requirement, washboard abs were not on my “Dear Santa” wish list.
Getting to Six Dates
My first post-marriage relationship, the one that got past six dates, was with Ernie, a hilariously funny former actor and comedian whose wicked smile made me melt every time. Our first date, in a dark lounge with a jazz band playing and prohibition-inspired cocktails, was tipsy and silly and full of magic … and seemed to last for hours and hours. At one point he leaned in and, flashing his mischievous grin, whispered, “Everyone in this place thinks we’re madly in love. They have no idea we just met tonight for the first time.”
‘Everyone in this place thinks we’re madly in love,’ he whispered.
But, six months in, I realized I had actually ignored the very clear signs of deal-breaker #1: He was never looking for something serious and lasting. And, as much as he was enjoying what we had, progress stalled out early on. For instance, he wasn’t really interested in taking it to the next level—meeting each other’s families, spending holidays together, introducing me to his daughter.
I called him on it, and we admitted that we were looking for different things and went our separate ways. (It was then that I learned an important truth about dating now, in the era of social media: You will never get over an ex until you stop following them on Facebook. I suspect every high-school kid knows that, but it was a hard lesson for me.)
As I went back to the dating apps, I went back to my list—taking it even more seriously this time and even working some of the details into my dating profiles to make my intentions clear. No, I didn’t write, “Only serious future boyfriends need respond!” Instead I wrote “If you’re only looking for FWB, ONS, hook-ups, or pen pals, move along folks … Nothing to see here!” (See sidebar to learn the online lingo.)
Eventually, I met John, a fellow “new to dating” divorced dad who channeled his energy into daily kickboxing.
He dropped me off near my apartment and leaned over to hug me good night, not even unbuckling his seat belt for a kiss.
We had polite drinks at a bar that’s actually a boat docked on the West Side of Manhattan. When they called “last call” early, I suggested another spot, but he looked at his watch and said it was late. He dropped me off near my apartment and leaned over to hug me good night, not even unbuckling his seat belt for a kiss. I shook my head as I walked home—clearly, no manufactured fireworks there! But I had to wonder: if there aren’t any fireworks at all, was there any attraction? The dating rules told me to maybe abandon all hope. Should I?
Let me cut to the chase: Months later, long after I discovered he really was attracted to me and that he actually fit all of the criteria on my lists—Makes me laugh, check! Calls me on my shit, check!—I asked him about that very buttoned-up first date. At the time, we were packing up his gym clothes and preparing to move in together. (See, it does happen!)
Turns out he had been getting a lot of advice, too.
“I knew right away that I liked you,” he said, “And I didn’t want to send the message that this was a hook-up or make it just about sex. I wanted to do this the right way.”
We looked at each other and laughed. The right way. As though there is such a thing in the online-dating trenches.
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A version of this article was originally published in March 2018.