Dating at Forty-Something: a Tale of Fifty Bad Dates and One Good One
By: Adriana M
Tags: Dating, Love, Nonfiction, Relationships

The guy I thought had died

This one is a ghosting case so incredible I think it deserves to be investigated by the team from the TV show Ghost Hunters. A lawyer in his 40s, decent looking, we went on three dates. I have to say I was making an effort to give him a chance because there were no significant red flags about him, except perhaps he seemed somewhat bitter about his divorce.

In any case, I was not completely relaxed about him. His body language was that of an insecure person who has trained to cover it up; maybe he had learned the tricks of looking more confident than you feel during his time in Law school.

We were located about an hour away from each other, so for the fourth date, I asked if he could come my way. The plan was to go wine tasting close to my place. He agreed. We talked around noon on a Saturday, and he said he would make a couple of stops before getting to my home, so I calculated it would be 2 to 3 hours before he will arrive. Just in case, I got ready in one hour and went about my business until the time came. Then three hours went by. And four, and five.

Finally, around 8 pm I texted him to ask if he was ok. I mean, when a person says they are about to go on the highway and never show up the first thing to do is try to make sure they didn’t have an accident, right? I got no answer.

The next Monday I told the story to my friend, and she agreed it was terrifying to think that something serious may have had happened to the person that is supposed to meet you but in this era of dating apps you have no way to know what happened to a person you just met.

I am happy to report that he is alive — a few weeks after the incident, he changed his profile picture on the dating site. And if you haven’t guessed yet, he never contacted me again.

The guy who didn’t care what I was talking about

This one I have to say fills the stereotype of the man that feminist ranters hate: conservative, mansplainer, one hundred percent focused on my looks. To be fair, though, he was not a bad guy. He was the proud father of a beautiful adult daughter, a hard-working man with a stable job with benefits and very polite. And he did pay for dinner. But it was 2016, and political opinions were the kiss of death for many a relationship that year and the years after “The Election.” And he gave me an earful on his position and how excited he was with the prospect of the “genius man” about to take over the most important office in the country.

When I said that as the single mother of a queer child of Latino descent I was unable to agree with him, he looked at me with googly eyes and said, “Your accent is so sexy, and that hair, so black and beautiful.”

Now, let me be clear — I think the phrase, “Your accent is so sexy, and that hair, so black and beautiful” is a compliment if taken in a neutral context. I like knowing that my hair looks nice and that people find my accent cute. But come on, man, can’t you see that my dark hair and charming accent are the reasons why your political views horrify me? Well, long story short, he didn’t understand that even after I explained it in a series of emails we exchanged the next day.

He kept asking for a second date and I kept saying we were not a good match. In the end, I had to do what I was trying to avoid out of politeness: I said, “I will not go out with you because I do not like you, not even a little bit, not at all.” And I give him kudos for his polite response, which was, “well, that’s closure.”

The guy who needed some time to get over his divorce

Brilliant, charming, dorky-cute, I was fascinated by this Harvard graduate and Theology professor. He spoke fluent Italian, could read Latin, Coptic, and Aramaic, was an avid reader and writer, and we never ran out of conversation topics. But he had jumped on the dating pool while his divorce was not yet final, so he had lots of unresolved issues, both legal and emotional, although he was very much done with the marriage and living in a different state from the ex-wife.

We dated longish distance (a two-hour drive) for three weeks. During that time we had some wonderful dates and when we apart, did facetime almost every day. Then his divorce sentence came, and it was a messy, confusing mandate that included 50–50 shared custody while the parents lived in two different states. So he asked for some time to pick up the pieces of his life and figure out how to work this out.

I thought it was fair and said to myself maybe six months would be a reasonable amount of time to give him. I unfollowed his Facebook to avoid temptations. At six months on the dot, I re-followed him. He was married, and I do not mean remarried to the ex. He was married to a new one — end of the story.

The guy that moved far away for a long time

This title drips with sarcasm because the guy did move, to a place one hour away (so far!) for a month (such a long time!). And yet, apparently, that is enough to never talk again to the person with whom you had five quite lovely dates — talking about feeling unappreciated.

I am grateful this happened to me after I was already forty-plus because in my twenties I would have thought it was my fault. I would have probably thought something along the lines of, I am too fat, and he is surrounded by supermodels every day. But nowadays, I know better.

If a person spends some pleasant time with me and then chooses not to call again, it is their problem. There seems to be a mentality going around in this age of dating apps where “dating” means “go out with as many people as you want,” so I can imagine that people wired to switch gears constantly from one prospect to another may feel like they accomplish a lot. To each their own.

I kissed a girl, and I liked it

I talk in more detail about this adventure in my piece I kissed a girl, and I liked it: reflections of a heteroflexible woman. Suffice to say that I had a lot of fun in those dates, and at least the connection and chemistry of the first few dates were much more comfortable and relaxed than in heteronormative dates, but alas, they did not last very long.

The one good date

I have known JJ for a long time, and we had very flirty interactions years ago, but the timing was never right. One of us was always dating someone else or not in the right headspace to get serious with anyone. I had not heard from him in years, as our circle of friends had dissolved with a lot of people moving away. I had been thinking about him again for about six months, but I didn’t dare to make contact. Maybe he won’t be receptive, just as I had not been very receptive to his advances years ago, I thought.

But the Universe brings us what we wish for, so one fateful summer night he contacted me on Instagram, which is the modern equivalent of leaving a note on somebody’s school locker. We engaged in witty banter just like old times, and I’m happy to say that that first conversation ended in a lunch date. It’s been over a year, and we are still making each other laugh.

Oh, yeah, and in love.

© Adriana M 2019