Dateline: "Karaoke. All of my anxieties in one."
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11:49 p.m. - We're off to an early start. She's a night-hawk and I'm a coffee-addicted insomniac. We opt out of the dinner-and-a-movie type thing and decide to pick a spot in the middle of the city and see where the night takes us. She's from deep Brooklyn and I live on the Upper East, so Midtown is a good central location.
12:00 - She looks like she crawled out of the pages of Sin City — bright hazel eyes, a messy bob hair cut, and a tight black dress. I swallow down any amount of suaveness I have left and sputter out, "Hiya!" She smiles. "Hiya back. Were you waiting for a long time?"
12:01 - "Nah, I was just wandering around," I say. "I'm never in this area, so I wanted to check it out. It's like Gotham city, kinda." Mental note to ease up on the comic-book references. She laughs: "Ooh, nice. Can I be the Riddler?" I'm in love already.
12:25 - We've been wandering for a while, trying to find food. The plan is to mosey around until something catches our eye. I don't tell her that I've already eaten at McDonald's, because I demolish fast food when I'm nervous. I'm not the best at making conversation, but she's got it covered. I don't feel weird when I'm with her. That, itself, is kind of weird.
12:30 - A little twenty-four-hour diner pops out of nowhere. "Oh my God, this place looks like a dungeon. Let's go in!" she says. I laugh and ask, "You really want to go here?" She get behind me and pushes me through the door.
12:45 - Two enormous plates of pancakes, bacon, sausage, and toast appear in front of us. My appetite comes back with vengeance. We dive in. I've never seen a woman shovel that much food into her mouth with such ferocity. I feel like a total wimp, picking at my bacon. "So what do you like drawing?" she asks me. I tell her how it's mostly corporate stuff — pamphlets, brochures, occasionally a magazine. "Oh! But I did do this poster for a Guns N' Roses cover band!" She's silent.
12:49 - "I was thinking about what you said about Guns N' Roses," she finally spurts out. "I don't usually do this on the first date, but… we should do karaoke." My heart pounds in my chest. Karaoke. All of my anxieties in one. "Okay, let's do it."
1:12 - We find a little Japanese dive bar with a neon "karaoke" sign. The bouncer outside looks like he could be a Yakuza enforcer. She's unfazed; she's getting cooler by the minute.
1:14 - "Are you nervous?" she asks. "Yup!" She puts a song on the list and orders me a sake bomb to loosen me up.
1:28 - I'm loosened up. It's our turn. "What are we singing?" I ask. The all-too-familiar opening of Biggie Smalls' "Juicy" starts up.
1:29 - We try our best to wreck this classic. It doesn't matter. I've never felt so calm while being so terrified.
1:37 - I offer her a cigarette outside. She says yes. I light it for her. We lean in and kiss. I miss and get her nose, she giggles and re-directs me to her lips. Direct hit!
1:45 - I walk her to her train stop and she commands me to call her again "…under the threat of total annihilation." Man, I am so full.