Dating Diaries: The Not Ready for Prime Time Player

New Year texts with a marketing Mad Man

Is this the Substack title you’ve all been waiting for? I had no intention of sharing details of my dating project when I started, but I’ve learned so far that the dates come and go, but the story sharing and chatter with the girls lasts forever. I’m committing to toeing out openly and intentionally, and sharing the take aways here - with reader submissions too! Thanks for playing along.

I write you from free Whole Foods Market Wi-Fi, slunked into a corner booth between cheer practice drop off and pick up. I am licking the last of fresh love wounds - the first to appear in a few years. I’ve tried walking them off but fear there’s no balm like writing about it to the girls, so let’s start off.

I appreciate you *holding space* and taking part in this exercise with your understanding how deeply humiliating this is for me.

tldr:

You just never know what’s going to happen next, I guess, and the start of 2025 was when I got stomped by a crush.

If you need to catch up from here, we could say January 2023 was when I began to logistically end my thirteen years of marriage. Living abroad at the time, it was a bit sticky, as was the litigation of our divorce that took over a year. When it came to boys or thinking beyond the day-to-day of that darker, more private chapter of the last two years, I couldn’t have cared less. And as that’s all wrapped itself up, I still feel so shell shocked at times I have to ask myself if I want any kind of new variable in the picture when considering dating.

I was 21 years-old on my first date with my husband, and as I meet new people I’m remembering what I’m attracted to, while trying to be open to new things. I remind myself that just because I’m attracted to it, doesn’t mean it’s right for me. The hardest part of the idea of dating for me is guessing where to find the sign to start, so I am lucky to have good friends.

At a Holiday week mood board night with my girlfriends, I promised the group of girls a date in January, “because it wouldn’t kill me.”

To deliver, I tried an app they suggested. This experience is so energy draining for me. Lonely men and people who don’t know how to market themselves make me so sad. I swiped the wrong way until my finger was sore until I paused on one, a 42 year-old (same age as my former husband) marketing executive from the Midwest living in the Design District.

Something about his profile was just. my. type. Cute in pictures, tall-ish, bookish, basic information checks out and a quip about George being the best Beatle - I was already laughing. We must never let him know this, but he could serve serious Don Draper. I like good on paper. I am pretty, he is handsome, we are both employed and smart - this is easy. He had liked a picture on my profile of me setting the table. There was something about him that was just soo cute.

Honestly, having no idea what to do next, I asked him if he was free the next time I was, which, now that I was looking at my calendar was January 19, a little more than 21 days from now.

We had a date on the calendar now which is like a date, right? Me and a cute boy, face-to-face, the whole day ahead of us? I felt pretty victorious that I had something on the books with a person that appeared both sane and nice the first day I was online.

I never take a black marker to the calendar, but I circled all of January 19, a three-day weekend Sunday, just for good measure.

As for what was supposed to happen between now and the date three weeks later, I really had no idea. Kind of a long time, tbh!

What a week. These are those magical dead days of the year, when no one knows what day it is and I’m in my kitchen more than my office. Nancy Meyers is everywhere you look. The story line of an online spark turned to so much more is so especially plausible this time of year.

Each day, I was getting more into this boy from Illinois that texted in the morning, worked hard at his job, was nice to his Mom and visited National Parks. In the first days I found him to be intelligent, consistent, kind and complimentary - of surface things I like but also my dedication as a Mother. This was first cute boy I had met who liked to go camping, and I thought of all the great stories in this book of Ina and Jeffrey camping and eating all over Europe. Everything was exciting.