1. The "Is It Still a Date If He Gets Arrested Partway Through?" Date
Somewhere in the camp of our second to fifth time hanging out, we were walking around the Upper East Side, got some beers, and decided to drink them on a bench in the park along the East River. The cops drove by several times and totally didn't care about what we were doing, but we didn't realize that it had gotten late and the park closed at 1 a.m.
At approximately 1:05 a.m., a cop car pulled up behind our bench.
TURNS OUT my date had been arrested the past New Year's Eve for public urination (I like 'em classy). That cop had chucked him on the ground, and when he tried to shield his face, they said he was obstructing an officer. After a night in jail, he got community service, which he did, but he hadn't filed the paperwork yet, which meant there was an active warrant out for his arrest.
The giddiness of what had honestly been a really fun date was fading pretty quickly! Two other cop cars showed up too, so it was six cops versus the two of us, so we couldn't even fight 'em off. To get a rise out of him they finally, classily, insinuated that I was a hooker, but he stayed calm (or unchivalrous, depending on how you look at it). Then, when he was in the back of the cop car, the cop turned to me and was like, "Ma'am, you should really leave, the park isn't safe at this time of night." And I was like, there are six police officers here ... but I guess I'll WALK OUT ALONE!
I walked home but I had to pee soooooo badly from the beer, and the hour it took them to arrest my date, so on my way home I hopped a fence and peed in a really pretty Park Avenue church garden and I'm NOT SORRY.
2. The Not-Date, To Date, To Not-Date Again
I moved to New York for a new job just over a year and a half ago. When I announced my relocation on Twitter, I received an email from a name I vaguely recognized. "I hope you're settling into the city and your new job with ease. I've been meaning to get in touch and invite you for a drink," she wrote. "It's been so long, we have so much to catch up on."
After some momentary confusion, I realized we went to college together. But despite attending a small, liberal arts college, I didn't really know this person at all.
I met her at a local bourbon joint and we chatted and I made things incredibly awkward by point-blank asking if this was a date or a booty call or whatnot. It wasn't, but the next week she invited me out on what was very explicitly a date. We went on excursions a few more times, but there was eventually a mutual, if unspoken, agreement that we were not destined for a romantic relationship based on some updated When Harry Met Sally meet-cute. On the upside: She has become a good friend and confidant.
3. The "Who Orders THAT" Maybe-Date
So... I was in college and this girl and I met through some friends. A group of us were supposed to go get food together, but everyone else bailed except the two of us. (I believe they all secretly planned to bail.)
The "Is This a Date?" moment happened when the both of us went to Chipotle together (romantic, I know.) It was super awkward, and I didn't know whether I should pay for her, or not ... I mean, will I come off too strong? Is this a date, or isn't it?
My decision was made when she placed her order. She ordered a plain cheese quesadilla... I mean, come on! You have all the options in the world at a Chipotle and you choose that?! From there, I decided that it wasn't meant to be.
4. The "I AM Married and Have a Child, But..." Maybe-Date
My last day at an enormous retail store, I buzzed around swapping numbers with co-workers. One I had stalked previously responded very enthusiastically to hang, and soon. Another friend warned me, "That's weird he wants to go to The Park with you. He, like, lives with his girlfriend and their child."
Two days later, he picked me up in his sedan...with a toddler car seat in the back. "Cool car seat," I said. He spoke freely and lovingly about his daughter, his partner, and their life together. We parked and unpacked a killer picnic, continuing conversation about our lives. He told me more about how he met his girlfriend, his career aspirations, showed me his marine animal tramp stamp, normal stuff. It was a friend thing, but with date-like undertones, especially with the way he scooted closer to me.
After an hour or so he touched it: "So you're probably wondering why I invited you here if I have a girlfriend, a kid and so on." Sure, yes. I was. He explained his partner granted him essentially what was a hall pass while she and their child spent the summer out of the country. The two were due back in New York in a week and a half and I was apparently his panic pick for guilt-free sex-making. We kissed a little while circling a lake, and made dinner plans, but I bailed. I couldn't imagine even watching a movie among family photos and toddler paraphernalia, even if everyone was OK with it. But yeah, surprise! Date, I'd say.
5. The "High School Mean Girls Ruin Everything" Maybe-Date
In my sophomore year of high school, a guy I had a crush on since elementary school asked me to hang out. I was really excited to hang out and definitely liked him but didn't think it could possibly be a date. We went to the movies, and he paid, but again, I didn't think it was a date. I thought it was just convenient (queue Doug Funny–Patty Mayonnaise date scene, on repeat). But THEN we got into the theater and the most magical thing happened: He put his head on my shoulder and held my hand. I repeat: HE HELD MY HAND. I was so nervous, like, wondering-if-the-other-person-can-hear-your-heart-thumping nervous. He continued to hold my hand, even when we ran into his friends. Let me tell you, 15-year-old me found this EXHILARATING.
Anyway, we ended up seeing the mean girls of my high school between the movie and the car. I didn't think much of it at the time until they IMed me the next day to ask if we'd been on a date. I shouldn't have written back but I think I wrote "We were hanging out" or something vague. All I know is that he stopped talking to me a few days after that girl IMEd me, AND THEN SHE STARTED DATING HIM. I don't know what she said to him but I think it must've been something cruel. Or it was never a date. This is giving me anxiety to think about. WAS IT A DATE? I'll never know.
6. The "Reluctant Wedding Plus-One" Maybe-Date
I've never really been one for "dating," but I have been one for "remaining hung up on my ex-boyfriend for many years." At various times since we first met 13 years ago, this particular ex — let's call him Will — has also been my boss, my best friend, my roommate, my dog co-parent, my pen pal, my collaborator, my friend's boyfriend (ugh), and the one that got away. At some point after our second breakup and before we entered the relatively smooth period of friendship while we were both safely dating other people, I used to end up at his house more nights than not.
It was during this spectacularly low point in my romantic life when Will's best male friend "John" sent out wedding invitations and didn't invite me — naturally, I guess, since I was an ex-girlfriend. I saw the envelope sitting on Will's countertop and unsubtly asked if he was using his plus-one. I said, "I always loved John." Backed into a corner by my incredible awkwardness, he said no, he didn't have a date in mind, and "Would you like to come?" I somehow managed to take this as a real, natural invitation to join him at the wedding — ridiculous considering I had basically just invited myself.
So we went to the wedding! We had our portrait made together, we danced together, we toasted a thousand times, and we answered several questions from various people who'd known us when we were dating about whether we were back together ("No," he'd say. "It's complicated," I'd tell the ladies in the bathroom.). I had a great time, but at some point late in the night, a feeling crept up on me that I had forced my way into this wedding in a farcical manner and that this was all hollow theater.
...Then we went home together and made out all night.
7. The "Is this a Date or Is this PR" Maybe-Date
I was working on a story and needed a quote from a woman at a well-known financial institution. When I looked to see who the company's PR contact was, I discovered it was a guy I knew from high school. He was your standard beer-drinking, football-playing bro, so when I emailed him, I did it with a "You probably don't remember me, but …" opener.
We ended up getting a drink to "catch up" and DAMN, that boy had grown up nicely. His company bought all the drinks (and there were a lot of them) but I couldn't gauge his interest level. Were we flirting? Networking? I didn't know. He definitely seemed interested, but he never made a move. Over the next few months I'd get texts from him here and there, sometimes with PR updates (though I quickly learned he was terrible at his job), and sometimes late at night about nothing in particular.
A few months later we had plans on the books to talk about work stuff. This time, though, he texted in advance to let me know he had "just broken up" with his girlfriend and so really needed to have a good time. OK. Well that seemed to have solved it. We made out. I brought him home. We did this a few more times.
And then, as beer-drinking, football-playing bros often do, he disappeared. Until he heard about my new media job and started texting me again — about PR.
8. The "Even Meeting on OkCupid Isn't a Sure Bet" Maybe-Date
When you meet someone on OkCupid, it's normal to assume you're going on a date. But of course, this is the internet we're dealing with, and things are never that cut and dry. I met B at a coffee shop, which felt like neutral territory, but we followed that up with a movie and drinks: definite date activities — at least, theoretically. Throughout the night, I tried to gauge his interest subtly by asking what he was looking for in a romantic partner and staring at his crotch. By the time we got to our last destination, a piano bar, I felt pretty certain we were embarking on an actual romance.
It was after buying B his fourth overpriced martini that I noticed he was texting someone. I not-so-casually leaned in for a closer look and soon realized his texts — while not explicit enough to earn the "sext" designation — were clearly headed in that direction. I was too drunk to fully process the fucked-up-ness of the situation, but I did at least grasp the fact that I was not on a date, and that B was about to go home with someone who wasn't me.
Which he did. I know this not because I witnessed it — I fled in drunken near tears as soon as I got a clear read on the situation — but because I asked him for details the next day like the true masochist I am. I ended up telling him I didn't mind at all that he'd led me on and let me buy him four overpriced martinis, and he told me that I'm, like, a really cool person and he was excited to be friends. "Maybe we'll even make out one day," he offered. Cool, yeah, looking forward to that. I wasn't holding my breath.
9. The "Is It a Date If It's Haunted" Maybe-Date
Once when I was working at my college radio station I had a crush on the programming director, aka college radio ROYALTY. One night he randomly calls me (I think he got my number through my roommate) and asks, "Do you want to see a haunted bridge?" The answer was, "Hell yeah I want to see a fuckin' haunted bridge." That's not your typical date spot, so I wasn't sure if this outing was a date. When we got there he told me a bunch of scary stories, and then said the rules of the haunted bridge were that you had to walk to one side, walk back to the middle, sit down, and tell a ghost story. We freaked ourselves out so much that of course immediate hand-holding commenced. I still count it as the best date I've ever been on.
10. The "I Inadvertently Invited a Third-Wheel" Maybe-Date
My current girlfriend and I had been nursing respective crushes on each other across our friend group in San Francisco, without realizing we liked each other back. When we'd hung out in the context of parties or a barhopping night, it'd just be friendly, as opposed to obviously flirtatious.
You couldn't blame me for thinking, Oh, she's just a cool, friendly, confident, pretty girl, so she's probably not into me. I mean, she had a lot of friends that were dudes, so the fact that she wanted to be friends with me didn't imply that she was into me. And to her, it just seemed like I was playing it cool as hell. (Side note: I've never before or since been accused of playing it cool as hell).
One late-morning Saturday, she called me out of the blue to see if I wanted to see a movie: the almost-immediately-forgotten Will Ferrell vehicle, Semi-Pro. In her mind, this was a bold crossing of the friend divide to suggest a definitive date. And I just assumed, "Cool. We're becoming better friends. Maybe once we know each other better, I can get her to actually be into me."
So what did I do? I invited our mutual pal and Will Ferrell enthusiast to come the movie with us. Date dumbly turned into group outing. She thought I wasn't into her. I wondered why is she being weirdly aloof as we waited for this movie to start. And it wasn't until, like, a month later before we finally made out for the first time in front of Zeitgeist with our bike helmets on.