Looking at the two of us, you might’ve decided, “He’s a douche bag and she’s a dumb blonde.” You’d have been at least half right. We had nothing in common on the outside but everything on the inside.

The table cloth of our first date might as well have been a red flag. He suggested a little French bistro on the Upper West Side and I was intrigued. Who was this man and who did he think he was, suggesting dinner on a first date? It’s 2016, no one does that! He must be a romantic!

Nope. He’d just broken off an eight year relationship.

The last time he was really single, he was in college. Aw, how cute: Someone who doesn’t know how the kids date these days! And hates Tinder because his ex used it to cheat on him! Adorable: He doesn’t know things you SHOULD NEVER MENTION on first dates!

He poured over the wine list like I pour over Playbill while waiting for the curtain to rise at a Broadway show. “Do you want to share a bottle?” he asked. There’s only one answer to that question on a date. Duh. He asked my preferences and I was honest. I know fuck-all about wine, I’m not going to pretend otherwise. “Most whites, I guess? Except Chardonnay. Reds that don’t stick to my teeth and remind me of blood? Honestly, red wine scares me a little, I’m prone to spills. I get voted “Most Likely to Break A Glass” at bachelorette parties.” He didn’t laugh at my joke but started telling me about a book he’d read about wine.

I zoned out as he described how the book had fucking changed his life or whatever. Fuck. I’m on a date with a snob.

“I know so little about wine,” I said, “I happily drink 3 Buck Chuck from Trader Joe’s all the time. You should pick the bottle.”

After our server poured our glasses and we clinked them together awkwardly, I learned something. Snob selected wine is significantly better than shitty Trader Joe’s wine. Dammit, at almost 30, I can tell the difference.

We talked about the things you talk about on first dates…but not in a fun way. He hates his job as a consultant and feels like a prostitute working for a Fortune 500. He works insane hours, but makes a lot of money. He lives way uptown in “the hood”, but only because he’s saving for a house.

That’s when I should’ve said, “You know, I don’t give a shit how much money you make, as long as you support yourself.” But I didn’t say that.

Being with a negative person makes me go a little nuts. I do everything possible to counter act their energy and brighten the mood. It’s a defense mechanism, I must do everything in my power to resist their black cloud of Eeyore gloom. I jump into the role of cheerleader, entertainer, painting metaphoric rainbows and unicorns all the way, man! Ugh, it’s disgusting.

As I drank more wine, I only tried harder. I can make this date fun all by myself! Look at me! I’m witty and adorable! You can’t help but smile! I’m so delightful I can pull you up from your wallow of sarcasm and cynicism!

And you know what? I fucking succeeded. Me and my sidekick, that half bottle of snob-approved wine, prevailed. I left with a pleasant buzz thinking, “Hey! That actually was kind of fun! I was actually able to make him laugh a couple times! WINNER! TOTAL SUCCESS.”

And here’s where this story takes a turn.

I said yes to a second date, then a third. Here’s the truth: a part of me was incredibly attracted to his Eeyore gloom. Misery loves company and I’ve been struggling with depression recently. That was the only thing we had in common and it was enough. He wore his gloom on his sleeve and I hid mine behind layers and layers of ruffles and silk, pink leopard print and decorative zippers. I have a degree in Theatre Arts that I use primarily to hide my depression. We were horrible together and I knew it. But drinking expensive wine and letting his problems distract me from my own was too much to resist.

He texted me at 3AM last night.

I know exactly how you feel! I feel exactly the same!

“Oof, I’ve had nights like that and they’re rough. But I bet you didn’t start tearing up on the subway ride home like I have before.” That was my response. Hey girl, I can see you through that humor your hiding behind. 

A couple hours later he texted me that we shouldn’t see each other any more.

So it’s back to my 3 Buck Chuck and my own problems. Let’s hoist bad-ass pirate red flag, drink cheap wine, and figure get shit together.

 

Thanks for reading! Until we meet next post. Or check me out on Twitter, Instagram, and Snapchat @newyorkcliche. Leave a comment and let me know if you relate to this at all. I hope I’m not the only person who’s ever dated a guy for his depression…god, that sounds so awful.

If you need a laugh after this Debbie Downer ending, click Kristin Wiig at the top of this post and watch one of my favorite SNL shorts.