Brief Lessons from Brief Men
Today, it’s warm out. I went for a long walk in the sunshine, took a gummy, and tucked in for a chill, solo night in. And because I live alone and I can, I decided to have a “naked night.”
“Naked night” is becoming a tradition in my apartment, and it’s inspired by a guy I matched with on Feeld last year. He was hot in a laid back way, lived at the beach, was age appropriate and kind of a slow burn on the messages. He mentioned that he liked to have a naked day every once and while, just lounging around his house naked, reading, writing, watching movies, and hanging out. I loved the idea - it tapped into my hippie summer camp skinny dipping days and how much I love a European nude beach. I find myself having a little ‘naked night’ every once in a while, and I always think of him.
We never met up. I unmatched him when I asked him out and he never responded. He was only a quick flutter in my dating history, but his impact is frequently felt. If anything, he’s improved my life more than most other men I’ve dated. Morale has been fantastic since introducing my own naked nights.
All this got me thinking about the things I learned or took away from men who were in my life most briefly. So here’s a list:
Jordan - we worked together on a Kickstarter campaign for his side hustle company (it was 2012, ok?). I think we had a crush on each other, but his cofounder asked me to keep it in my pants until the campaign was over. He was dating someone else by then. Before we lost touch, he recommended a little known, just opened pizzeria called Una Pizza Napolitana in SF. Lesson: restaurant recommendations are valid even if the connection died.
Don’t remember his name - met him on Bumble or Hinge, and we swapped phone numbers to coordinate meeting up. He texted me incessantly asking for my birthdate. When I said I wasn’t comfortable giving it to him because we hadn’t met yet, he flipped out and told me he could find me and where I live with just my phone number. Lesson: don’t swap phone numbers until you’ve met in person.
Don’t remember his name, either - way back in my 20s, I went on a date with an older guy (I was probably 26, he was 30 lol). When it came time for the bill, I reached for it to be nice and somehow ended up with a very transparent conversation about how men will always pay for the first date if they want to see you again. We didn’t vibe and never went on another date, but the check dance has stuck with me. Lesson: let him pay on the first date - if he likes you, he won’t hesitate. If he does, you can throw that one back.
Investee - A few years ago, I asked out a founder from one of the portfolio companies I invested in. I had known him for four years at that point and had always had a crush on him from afar. His vibe (and a part of his core appeal) was that integrity was important to him, so I never dreamed of asking him out until after I left the job. But a few months later, I emailed him to ask him out and he actually said yes. We planned a whole date and then he had to cancel the day before. Then we rescheduled and I got sick. We never coalesced again. I think about the courage it took to ask him out a lot and how proud I was of myself after. It gave me my big Dead Poet’s Society energy. Because, well, I did it. Lesson: the worst they can say is ‘no’ or ‘hell no’.
Tony - the Lebanese fashion designer who told me that my standard first date dress was well made and beautiful. Lesson: now I have a go-to first date dress.