I decided to expand my horizons from my usual type- hot, cocky douche in their late 20s/early 30’s…and try my hand at the older Gents club.
So I went for it. I widened my age range on my trusty dating app and swiped away, in the hopes of finding my own personal George Clooney. I matched up with Lenny, a handsome 50 year old recent divorcee. We chatted for a few days. He seemed really down to earth and cultured. He picked a super fancy restaurant for our date which was a nice change up from the typical “Let’s meet at ‘insert crappy dive bar here’” that I’d been getting up until that point.
In person, Lenny was a decent looking dude who looked youthful for his age. But tragically, all the signs of a mid-life crisis were there. I couldn’t help but stare at the guitar pick choker, the spray tan, and the tight V-neck shirt showing off his ample man cleave. In the right light, you could see a slight shimmer of grey peeking out through his Just for Men dye job. Taking all of this in, I had a premonition this date was going be a complete shit show…and my intuition was spot on.
When our food came out, Lenny said “Enjoy!!!” and gleefully waved his hand across the table. It felt like when I’d go sleep over at my friend’s house in middle school, and her dad would come in (wearing a sweet fanny pack), set a Papa John’s pizza down on the kitchen table and do the same little hand wave Lenny did. “Here you go guys!!” he’d say. Then he’d shake his finger “Don’t stay up too late now painting your toe nails doing girly stuff!”
So yeah, the Dad vibes were hella strong on this date… and it was killing any attraction I had. But as we often do as women, I calmly whispered to my vagina, which was already screaming in agony: “Ew he’s so old!” — “Come on!” My brain shouted down…”Just try this out.” Maybe his “dadness” will go away and the attraction will come soon?”
Well, I thought, it will actually be nice to feel like I have an upper hand for once with my “youth & beauty”…seeing that I am 16 years younger than my date.
So here I am feeling like hot shit, and as we start chatting, he drops the bomb and shoots a “dad dart” right into my nicely puffed up little ego.
Lenny proceeds to tell me the last girl he dated before me was 21 years old! So I went from feeling young and hot to an old hag in about 1.5 seconds. So I am 13 years older than his last dating relationship. Who would have thought Lenny was such a stud? Once that choker goes on… beware all you barely legal ladies! Dad-Bod is on the loose!
Then he went in on the details of his messy divorce: “My wife just went crazy…she lost her mind” he rambled.
Ahhh…the good old “my ex was crazy” defense.
So she was fully sane the first 14 years of your marriage but year 15…that’s when shit went down? Her “mental illness” forced you to end the marriage, forced your fingers to type out your douche-y new Tinder profile and forced your not- so-fit body into skinny jeans 2 sizes too small?
So long story short. I wasn’t buying his whole “my wife just went nuts” argument to justify his divorce and painfully obvious mid-life. And I could tell from the way he bragged about things that he was extremely insecure and looking for conquests rather than a genuine mature connection to a woman. I mean a 21 year old? Really dude?
At the end of the date, he leaned into to kiss me. I wasn’t expecting it and I literally flinched. His personality didn’t draw me in and the attraction just wasn’t there. So my vagina won out on this one (I think I actually heard clapping down there when I rejected the kiss).
He seemed really butt hurt about it and texted me the next day saying: “I don’t think you’re attracted to me. I think we should go our separate ways”
No problem Lenny. Thank you for welcoming me into the Dating Older Men Club with your little hand wave and then promptly showing me the door, all within a 24 hour period. Do I need to return my “I love Old Balls” membership card and hat? Or can I keep them as souvenirs?
Comical Cupid Dating Lesson: You can’t deviate too much from what you are normally attracted to and force something that just isn’t there. Telling myself “I should date older to get better results” wasn’t a genuine approach and set me up for failure. And it’s perfectly okay to listen to your vah-jay sometimes. Mine is cheering right now.