How to Date in Forty-Two Easy Steps

A few weeks ago, I met with Mo (made-up names and some changed facts here, folks) for coffee. We had been communicating via the dating app Bumble for a while, and he seemed nice enough. The minute I saw him in person I thought nope.

Mo was a perfectly nice fellow. MIT educated (not always a plus, to be honest), currently entering his second year of “taking a break” from his career in computer science, and focusing on mastering the perfect handstand (no, I’m not kidding), but the conversation’s flow mostly depended on my keeping it going.

Our uninspiring conversation ended after about an hour and I bid quiet, poor-conversationalist Mo farwell. From there, I drove to meet Curly at a brewery (yes two dates in one afternoon. I’m trying to be proactive). This brewery had a fun atmosphere; a fireplace, some pinball machines. I had been chatting with Curly via the new Facebook dating app.

For the most part, the Facebook dating app has offered mostly men with neck tattoos, or who pose in their photos with scantily-clad women. Sometimes both if you’re lucky.

But Curly had smart things to say, was capable of an actual conversation online, showed signs of a sense-of-humor, and had a great smile (a lot of men frown in their profiles because they think it makes them seem sexy. It doesn’t. It makes them unapproachable).

I entered the brewery and he beamed at me from his perch at the bar and stood to greet me and offer a friendly hug.

Gay. Definitely gay.

So, I enjoyed my date with new gay friend Curly with less pressure since I was pretty sure I’m not his type. He was in fact, intelligent, with an interesting origin story which he openly shared. He’d worked his tail off trying to make the lives of local kids better, and after banging his head against the wall with all the one step forward two steps back experiences, he shifted his job. Now he is still working to make the lives of local disadvantaged kids better, just in a different way.

We talked about movies and books, social justice and history, family genealogy (he told me I need to write a book), and when he walked with me to the parking lot, I was surprised when he planted one on me before giving me a hug, playfully tossing me back and forth while hugging me (that was a first), and then telling me that “next time we should go play some skee-ball!”

He never called. I’m cool with that. What I’m not cool with is someone who may be gay pretending to be straight. It makes me sad for them.

The following week, I decided to try something new and went to a Singles Mixer that I found off the website called MeetUp. The host claimed that he would keep the male-to-female ratio pretty even, which is important since that’s most often not the case (Years ago I went to a similar event which got cancelled when eight women and no men showed). After parking my car, I started chatting with two other women as we trudged our way up the four flights of stairs to the photo studio where it was being hosted. It was a cool space, and I knew that I, at the very least, wanted to be friends with one of the women. So that was good at least. I made a friend!

I spotted Ray, about my height, salt and pepper hair, after chatting with a few other people. I made my way over to him, and we enjoyed a solid 25 minutes of banter before I noticed something. He had no wrinkles. Like, NONE.

“How old are you?” I asked him, somewhat incredulously. This event was for singles between 35 and 55, afterall.

He smiled sheepishly, “Well,” he answered in a slight middle eastern accent, “I contacted the host and asked if it would be OK if I were a few years outside the suggested age range and he said that was fine”

Ray wouldn’t tell me exactly how old he was, so I blurted out “I’m 43!”

Once he put his shocked eyeballs back in his head (he later told me he thought I was in my thirties), he claimed it didn’t matter, and that we should hang out.

So a few nights later, we met for a meal and some rounds of pool. He made a few cougar jokes (not realizing until I told him later that it was actually an insult to keep making these jokes. I cut him some slack as English isn’t his first language and I was the one to first teach him the term), and I learned that he was, in fact…wait for it…only 27.

It was actually a real shame, because he has a great sense of humor, is intelligent, and most appealing, very open, unguarded, and un-jaded. I hope that doesn’t change in the next ten years.

But he was also born when I was in high school. So that’s a no.

Ray and I are connected via Instagram now and he recently sent me a screen grab announcing another Singles event for 35-55-year olds. I responded “YOU ARE NOT ALLOWED TO GO TO THAT, RAY!” He claimed he was sending it for my sake.

Last week I had a few dates. On Tuesday I met with John. He was a microchip designer who also painted for fun (nice stuff!), and volunteered at an animal shelter. He had no sense of humor, and when I told him I had put Harlow on Prozac, and he began to talk about how important exercise was to dogs, I felt judged and even less interested than I had been when I realized he didn’t get my humor.

That said, very nice man. Moving on.

On Wednesday I met with Jacob. Jacob had been messaging with me via OK Cupid for a while. He had a business trip, then came down with the flu. He was a self-described hypochondriac, who would ask questions like “How much time do you like to spend with your partner?”

I would answer something like “I’m an independent person, so I don’t like to be crowded, but in time I like to see the person I’m in a relationship often”

And he would repeat back what I’d just said, seemingly telling me what he thought I wanted to hear “Oh yes, I like to give my partner space!”

He was a bit strange from the start.

For our date we were going to meet at an outdoor art installation in Boston. He texted in the afternoon that maybe it was a bit cold out. Sensing that he was just a giant wimp, I told him we could just meet at the restaurant where we’d planned to get a drink, and I would check out the art beforehand. We went back and forth about this for a while before he finally said “OK I’ll meet you at the restaurant”


Fifteen minutes later, I got the following text “I am still not 100% fit, so I don’t know if it’s a good idea to me. I have a tired face. And, due to the dryness that you get in your throat, it is making me cough a bit. So, not sure how much will be able to talk. Lol. I might be coughing a bit all the time. Though my flu is gone. But you know right how you feel after a bad flu. So you might not like me as I don’t look my charming best😬”

And at this point I am annoyed and basically have no interest in meeting him in person at all. My couch and Harlow are lookin real good compared to Whiny McBaby over here.

I tell him that we can just do it another time since he’s not feeling up to it.

Then there’s an extensive back and forth about how that’s not what he meant and that he is interested to get together, ending with a heartfelt and encouraging “Yeah, we have had this plan for a while. I don’t like to bail out. So it’s fine by me honestly.”

Fine by you. Cool.

Meanwhile, I literally do not want to meet this complainer anymore.

I am a woman of my word though, so I make my way into the city, check out the installation which was boring as heck, and head to the bar. We sit together at the bar and the bartender puts ice water in front of each of us.

Jacob squirms “Oh, um, can I have some warm water?”

“You want some hot water, like, for tea?” the bartender asks.

“No, just some warm water. I mean not water with ice. But not cold water. Or really hot. Just some warm water”

The bartender wanders off and Jacob turns to me, “The last time I had ice water I got the flu”

Yeah, that’s not how getting the flu works.

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