Dating Story - The Fine Young Man

Let me tell you: having the flu and being dumped is an unholy combination. Such was the case about a month ago - Blondie had shut me down while I was laid up on the couch, drowning myself in tissues, then tears.

When I finally recovered from illness, I had a terrible case of cabin fever. I needed to be OUT IN THESE STREETS, feral as a wildcat. Throughout my cold, one guy had been messaging me almost daily, checking in on me and promising some homemade chicken soup. I even sent him progress updates on the enormous jigsaw puzzle I did while under the weather (yes, that’s how bored I was. 1000 piece jigsaw puzzle). My one qualm with him was his age - 30, and officially 9 years my junior. But he was cute and kind. When I was ready to leave the house, we scheduled a casual drink at the dive bar nearby to check the vibes and get to know each other.

I may have overextended myself and scheduled a long-overdue happy hour with one of my besties earlier in the evening. But showing up to a date with a drink or two under my belt would not be unprecedented. (Very rare! But not a first). So I rolled up to meet this man on a rainy evening, a little tipsy and ready to break out of the flu prison. And I was happily greeted by a confidence short king with incredible energy.

We made quick conversation about our backgrounds (both native New Yorkers) and our respective jobs (he in food, me in whatever I do). The bar we intended to go to was packed so we walked a few blocks to my favorite cozy cocktail spot. We stopped to make out mid-block before even getting that first drink. A quick but fun stop for cocktails ended with making out at the bar (maybe this is my new 100% success bar?) and some leading questions about what we should do next.

We decided to go back to my place for a “nightcap”, stopping for some quick make outs in the short walk. He marveled at my apartment and told me that he was in escrow for his own place. Did this young man have his shit together? More so than most of the 40-yr-olds I’d been dating? I was lulled in by his commanding energy and I proceeded to waste a delicious bottle of craft cider by opening it and pouring us each a glass that went untouched.

We got intimate - it was fun and creative, but sadly nothing to write home about. Lots of enthusiasm but no big crescendos, if you catch my drift. We made easy conversation afterwards, got some quality snuggles in, and he scurried home for an early wake up.

All this was better than I’d imagined - he seemed ready, able and willing to play the part of Boy Toy. I was impressed with his follow through, as he texted me every day in the days that followed. He cared! He was nice! He asked more questions than other men (ok 2 is technically not a lot but it’s more than 0!).

He was pushing for a second date but I knew I wanted to spread my wings and see what else was out there. So I was honest with him - I enjoyed hanging out with him but I was in an exploration phase, not trying to get boo’ed up. He caught my drift and lowered his texting frequency (which, phew!).

We made a date for two weeks after the first, which was still a lot of lead time. My calendar had become packed as my “cabin fever freedom” campaign continued. Now that I was back at full strength, I felt the strong urge to go out clubbing on the Friday before our second date and dance out the icky feelings left over from being dumped. I found a great DJ who I really wanted to see and when my friend couldn’t make it, I invited the young man to be my date for evening.

Enthusiastic as ever, he jumped at it. I was ecstatic - could I have found a hookup buddy who would be fun to dance with?? That would be ultimate dream. I had already purchased my ticket for this show so I sent him the ticket link and said I would see him Friday night.

Thursday he texted me: could I buy his ticket for him?

Now I’m not one to squabble too much about who pays for what. He’d made a big show of paying cash for the fancy cocktails at our first date, but I wasn’t quite willing to front his ticket. I’d had a couple incidents recently of having friends bail on me or forget to pay me back for tickets, so I encouraged him to buy a ticket at the door - problem solved!

Friday night rolled around and I was so excited. Great music, good company, late night fun - the expectations were maybe too high. We made a plan to meet at my place and I’d pay for the Uber to the venue - that felt like the right thing to do given I’d invited him to the event. I wasn’t drinking but wanted to make sure he’d feel comfortable to drink or not as he wished.

He arrived and - vibes were off. It was awkward, I don’t think either of us was really “feeling the magic” but we are both normal and kind people, so we went ahead with our evening despite not feeling as in sync. I felt the ick coming on in the car ride there, but ignored it, knowing we’d have a fun night regardless.

At the club, the DJ was already going strong. I was excited to dance so we got Young Man a drink and set off for the dance floor. I set about swaying with the music and taking in the crowd. He couldn’t stop looking at his phone. I know not everyone is a dancer but he wasn’t really moving at all, just sort of standing there. When he was engaged and not vaping or on his phone, it felt forced.

I started to disintegrate into awkwardness. Was this a mistake? Second dates are kind of hard to nail, but this was just not coming together. At one point, a really cute girl winked at him and in that instant, I was so happy for him. That’s when I knew I only saw him as a friend, and I wasn’t attracted to him.

I sat with that (or rather, danced with that) for some time. Should I tell him I wasn’t feeling it? Should I be honest? I had just suffered at the hands of someone else who didn’t take my feelings into account - could I break things off and help preserve his dignity? Was he even still into me?

The last question did get answered - he leaned over to make out on the dance floor and all I could taste was his vape. 🤮 I pulled back and I think he knew I wasn’t feeling it. I even tried to hold hands, but that felt forced and awkward too.

He wanted to get another drink, so we walked back to the bar where it was a little bit quieter. I decided to rip the bandaid off - I told him that I wasn’t feeling our connection anymore and that we would be going home separately that night. He was kind about it and held his head high. Truly, this guy was a Fine Young Man and didn’t deserve to be dumped in the middle of a DJ set. But I did not want to lead him on.

Like a champ, he stuck around for another 30 min, but announced he was heading home a little early. Fair enough. I was truly impressed with his gentlmanly handling of the situation. I stuck around after he left, enjoying the dancing and feeling the crowd. As if always intended for this night, I left nothing on the dance floor.

The next night, my guy friends incredulously yelled at me for breaking things off mid-concert. I knew I deserved it. But I also felt confident in my decision. I knew it wasn’t going any further that night or any night. Why drag it out?

Dating is terrible. No one deserves most of the shit they receive at the hands of those foolhardy others in the dating pool. Fine Young Man is no longer on the roster, but he is a testament that there are good guys out there and that diamonds can be found, if you just keep mining.

So high ho, high ho, it’s off to the mines I go once again.