We're collecting stories about your most entertaining dates. Send your time-stamped dating stories to email@example.com; don't forget to include gender and age for you and your date.
9:05 p.m.- I’m late. Ruffling through my underwear drawer, I try to decide between a pair of lacy boyshorts and a silk thong. The thong is sexier, but the lacy boyshorts are more historically appropriate for my flappers outfit. I decide on the boyshorts. Halfway to the subway station, I realize I never bought a pair of boyshorts. I'm heading out of the house in what I soon realize is my roommate's underwear. It’s too late to turn back.
9:20 pm. - On the N train, wearing thigh high stocking, a suede dress, black gloves, a string of pearls, and a fascinator. No one even looks my way. As the train rolls over the Brooklyn Bridge, I check my phone for a text anxiously asking where I am. Suddenly, it emits a jubilant ding ding! and the text reads, “Hey, I’m on the second floor. Where are you?”
10:10 p.m.- Arriving at the speakeasy, I say the password into the keyhole, “My grandmother is the one on the right.” The door opens, revealing a windowless parlor lined with plush chairs, a chandelier, and a fireplace. There are four women wearing stockings and a suspender belt crooning out 1920 love songs in one corner of the room. My date appears and looks down at me from the winding staircase. I am a little disappointed that he’s wearing a thoroughly contemporary outfit: shoes, slacks, a burgundy shirt. But the strong cologne that wafts from him as he plants a hesitant kiss on my cheek indicates he has put some effort into the evening.
10:30 p.m. – We sit on separate plush stools and go through the usual topics covered by New Yorkers on a first date. People on the subway are so crazy. Rent is so expensive nowadays. He grew up in Park Slope. I grew up in Bay Ridge. Remember when there used to be sneakers hanging from power lines and it was genuinely dangerous to go out after 9 pm? I miss those days. He agrees, nostalgically reminiscing about the time he got mugged after school by Manhattan Beach. “Oh my god! I got mugged there once too!” I yell excitedly. “No way!” he smiles. This is going well. Getting mugged in the same place in NYC is surely a sign that you’re meant to be.
10:37 p.m. – A couple on the couch across from us asks us to take a picture of them. We do. He asks them to take a picture of us. They do. He puts his arm around me as they take the shot, and when they hand the iPhone back to him, he lets his arm linger on the back of my stool. It has begun.
10:52 p.m. – I finished my first Manhattan ten minutes ago and have been throwing pointed glances at the melting ice cubes in my teacup ever since. He finishes his cup and asks me if I want another one. I smile and nod.
11:05 p.m. – When he returns from the bar with two cups, I have already moved onto the plush couch. It is still warm from the heat of the couple that has just left. As he positions himself next to me and puts his arm around me, I feel like we are carrying on the expectations of the couch, this haven that bears one couple then another in unceasing succession.
11:40 p.m. – We start talking about our favorite movies and TV shows. This is a pivotal conversation. My heart sinking, I listen him recount each of his regulars. He watches Game of Thrones, The Wire, and The West Wing. I watch How I Met Your Mother, The Office, and reruns of 30 Rock. No bingo. I bring out my ace card, asking him what his favorite Woody Allen movie is. He tells me he doesn’t really “get” Woody Allen. I make a mental note that this relationship is not going to go anywhere.
12:15 a.m. – I’m drunk enough now that I might be able to forgive the Woody Allen thing. Everything we have in common now seems to be of cosmic significance. I LOVE macaroni and cheese. Me too! I LOVE Martin Scorcese movies. Me too! I’ve always wanted to go to Yemen! Me too! Omg, let’s go to Yemen together! Let’s!
1:12 a.m. - I’ve had three Manhattans now and, lacking the enzyme to properly break up alcohol, feel inordinately happy. I keep my head turned down as we laugh, because I can feel the possibility of the first kiss buzzing around my head, and I always become oddly shy and adolescent in these moments. After one joke, we giggle longer than we need to, as neither of us knows what to say next. Fearing an awkward silence, I look up. The kiss seizes its opportunity. It tastes like three Manhattans and two cigarettes.
1:38 a.m. – Our kissing is broken up by the security guard’s rough cry of “Last call! Last call everybody!” I’m sort of proud that we’ve stayed in the bar until it closes. We both instinctively realize it’s time to go. Outside in the tunneled alleyway, he offers me a cigarette. I hate smoking but love the way it feels, especially now, wearing my heels and my white pearls and my red lipstick and black fascinator. We stand and smoke and chat, and I feel giddy as I feel like we’re in the bunker of some tunnel in the London underground during World War II. I wish he’d kiss me at this moment, but he doesn’t. We both finish our cigarettes. I take particular pleasure in crushing it with the front of my heel, and we move on.
1:57 a.m. - We enter the subway, arms wrapped around each other, supposedly for support. I pause at the staircase, supposedly to fix my heel, and we make out as I lean against the handrail. “I’ve never enjoyed waiting for the train so much” he murmurs. I agree. I bend my leg so that the heel slips off ever so slightly. He runs his hand along my legs, pausing at the small bit of bare skin between the lace of my stockings and the lace of my underwear. The boyshorts were definitely a good idea.