Dater X: The Best Worst First Date Ever, Because Of Course

Talk about “Ask and you shall receive.”

After last week’s uncomfortably confessional post, I decided I better put my money where my mouth is and get out On the Hunt. To that end, I have not seen El Guapo (my FWB, for those who asked; Esquire bailed on this week’s softball game at the last minute, because of course he did). But I did set up a first date, via my newly back-in-action Tinder account. Apparently, deleting the app and reinstalling it exactly five times over the course of a month is the magical answer to all Tinder-related problems. Armed with this information, I’m currently applying for a job with their woefully ineffective tech department.

This week’s Tinder guy, one of several that Newly Aggressive Dater X got to chatting with, looked cute and we bantered easily, switching from app to text after less than 24 hours and arranging to meet for a weekend afternoon cocktail in my neighborhood. Given my online dating track record (The Israeli Guy; the eHarmony guy with Tourette’s who asked about butt sex on a first date; very little else of note), I maintained justifiably low expectations – but I admit that when this guy texted me every day with playful little thoughts or just to say hello, I couldn’t help but be charmed. He offered to pick the place, but also said he was happy to come to my neighborhood, which is nowhere near where he lives. A perfect balance of deference and take-charge. So far, so good.

Saturday afternoon rolled around, and Tinder Guy – we’ll call him The Big Easy, for reasons that will become clear later – texted me an hour in advance to say that the buses were running strangely, and he would be late. No big deal; the spot we’d chosen to meet was steps from my place, so I figured I’d just leave a little later than I’d planned, and offered to have a drink waiting for him. I don’t love people who are late, but traversing the city on a weekend can be fraught, and at least The Big Easy had the courtesy to let me know in plenty of time, so I wasn’t sitting at the bar by myself.

Only I did end up sitting at the bar by myself. Because The Big Easy was not 15 minutes late, but 45. True to my word, I had ordered a drink in advance for him. Let me tell you: by the time he got there, that was one watered-down Bloody Mary. I had also befriended the only other couple sitting at the bar, a boisterous pair who grew more vocal with each passing minute (and cocktail) about this guy proving his worth in exchange for leaving me waiting. When he finally did arrive, they were practically ready to chase him off with torches like some Disney peasant mob – but he was so roundly adorable, so apologetic, and so simply sweet that he changed their minds. And mine.

The Big Easy marched right up, gave me a hug, apologized for being late, thanked me for the drink, and complimented the girl beside me (who was glaring at him along with her boyfriend like my feral protectors) on her jaunty sunhat, which immediately diffused her venom, and with it, her boyfriend’s. We laughed at the absurdity that is the public transit system on weekends. We sipped our cocktails. We ordered a snack.  We talked effortlessly. When I mentioned that I had walked by chalk drawings advertising a street fair on my way to the bar, he immediately insisted that we go try our hand at the carnival games. We finished our drinks and snacks, said a fond farewell to our new friends at the bar, and wandered off into the afternoon sun.

He won a game that involved throwing leather balls at cats. I won a game that involved throwing darts at apples. We exchanged prizes. It was like some feminist version of a YA novel: wholesome fun, easy conversation, the sun setting behind the buildings, each of us winning the other a prize. We headed to another bar to play pool and darts. To another bar to sing karaoke. The sun set.

And somewhere between our Meet Cute and me wailing Janis Joplin, we forgot to eat. So our increasingly drunk, but no less excellent, first date found us sitting on a bench in the park, me feeling a little weepy about one thing or another, him puking the bar snack (and several beers) that were the only thing we’d had the sense to put into our stomachs all day.

What can I say? I know how to pick ‘em. Because of course your Un-Dateable Dater X ended up on a first date with a guy puking in the park.

I worry that I’m not doing him justice here, so I’m going to try and let what happened next speak for itself: I got him into a cab, got myself home to bed, and the next morning, we spent an hour on the phone laughing at the absurdity of getting so drunk at our age, of forgetting to eat in one of the world’s great restaurant neighborhoods, of being so giddy about meeting each other that we overestimated our ability to, as the kids say, “hang.” And then he came to my softball game and spent several hours sitting among my friends while I haplessly fielded grounders and slapped infield singles, feeling uncomfortably conscious that a guy who I really liked was watching. And cheering. For me.

And what now? Well, a couple of things. The first is me grappling with how damned easy all of this has been (hence his name). I’m usually one picky motherfucker, but this guy doesn’t set off any of my multitudinous alarms: he’s sweet, but not a pushover. He’s funny, but not crass. He’s handsome, but not intimidatingly so. He’s polite, but not a wimp. Being around him feels like the most natural thing in the world. I am unabashedly, unapologetically myself around him. And he seems, bless his heart, to like that.

Another troubling thing happened today, and I’m having a hard time dissecting it, so I’ll just present it, as I have all the rest of this newness, at face value: there’s another guy. A guy who has frequently behaved badly with me, but who nonetheless makes me literally weak in the knees. He’s not a bad guy, though he certainly does bad things – but when he’s good, he’s foie gras on brioche with grilled peaches and balsamic drizzle good. Steamed lobster on the docks in Maine with drawn butter and August corn on the cob good. Red velvet cheesecake good. You get the idea. He’s the guy that, if he asked, I’d drop anyone and everyone for. And I haven’t seen him in over a year. So of course he showed up to play softball with the team today.

He flirted. I flirted. There was an obnoxiously intimate amount of eye contact, his blue eyes locking mine, smiling without meaning to. And then halfway through the game, his Flavor of the Week showed up, some sweet but nondescript blonde of the variety he favors when he’s not making eyes (and thighs) at me. Why today? Why, right after meeting someone easy, did this challenge suddenly walk back into my life? It was impossible not to think about The Big Easy, about how distinctly different the warm, comfortable thrill of being with him feels compared to this fucking firework, exploding right in front of me with all the gaudy delight of the 4th of July.

So how am I handling all of this? I’m getting the hell out of town, of course! A week’s vacation with my family (and no cell phone service) is just the thing to turn this simmering stew into a rolling boil of What the Hell Do I Do Now. And to be sure I’m as much of a mess as possible: tonight, I’m having dinner with my out-of-town ex, the last person I lived with, who wants to collaborate on a business project and buy me fancy wine.

Because of course he does.  Stay tuned.