I Went on a Date With a Guy I Met on the Subway

Jason Hoffman/Thrillist
Jason Hoffman/Thrillist

One December evening a few years ago, I rode a crowded 5 train home after a long day at the office, sardined between a blue-haired girl playing music without headphones and a middle-aged man with halitosis.

Finally arriving at my stop, I exited the crowded car quickly -- prematurely jubilant over the bottle of wine and leftover stir-fry that awaited me at home. It was then I felt a tap on my shoulder as a man's voice barked: "Excuse me!"

I'm a New Yorker, so I naturally assumed I was about to be mugged -- or, more likely, asked for spare change. I put a vice grip on my purse and turned around... only to be faced with a stunning man who appeared to be around my age.

"I spotted you from across the car," he started. "I had to tell you that you have the most beautiful hair." I was shocked; and though it was an obvious line, it worked. Not wanting to kill the moment (I was wearing hair extensions in excess), I quickly thanked him as the subway pulled away from us. I offered the man a flirty smile.

Blonde-Zac-Efron-in-a-suit introduced himself as Paul, and we began walking up from the depths of the 59th St subway station together while making small talk. Emerging onto the noisy, trash-riddled street (ah, New York romance!), Paul propositioned me: "At the risk of making a fool of myself, if you don't have plans, would you be interested in grabbing a bite?"

"You mean, like, right now?"

"Yeah. Why not?"

Why not? Paul had a point. Paul was also 6'4" and attractive. And I hadn't been on a date in forever -- the talent on OkCupid left a lot to be desired. We settled on sushi and wine, and so began my date with a guy I'd just met on the subway.

Not all spontaneous dates equal rom-com moments

It was pretty soon after the first course of seaweed salad and sauvignon blanc that I realized Paul was THE WORST. In the 40 or so minutes we spent together, he managed to brag about his almost-Ivy League education, dismiss my taste in music, give lip to the waitress, and showcase horrific table manners (who over the age of 7 rocks his chair back and forth into the wall?) I ate as quickly as I could and did my best to discuss something, anything, that wouldn't be divisive.

The bill came. "I guess I’ve got it," he sighed, "since I’m the one who suggested this." After an awkward ass-out hug, I bid farewell to Paul-5-Train forever.

Spontaneous beginnings afford spontaneous combustion

OK, so my impromptu subway date didn't end with some sexy after-hours time or romance-novel ending. But I still think of it as a positive experience.

In case you've been under a boulder, we're currently living in an era in which most romantic interactions are sparked via the Internet. I have friends swiping (mostly left) on dating apps that I'd previously never heard of: Pure, Twine, one about coffee meeting a bagel? I'm convinced people don't even make an effort to strike up a bar-side conversation anymore, simply because they don't have to. They’d rather spend that time out with their friends, and then later hunt for tail on their iPhones wearing sweats with The Big Bang Theory on in the background.

I'm certainly not against online dating (disclosure: I met my boyfriend on Match). But before finding a keeper (hi, Jeremy!), I certainly endured my fair share of trial-and-error with prior male suitors from the site. You know how it goes. You find someone's profile and photo decidedly un-revolting. You correspond over on-site messages. You eventually exchange numbers. You set up a first date, then continue to text a bit over the course of the week. Maybe you even talk on the phone. You like him! You're positive you’ll hit it off in person because you're both from Westchester and love the movie Fargo and working out. Then you finally meet... but he won't stop talking about his goldfish, is 4in shorter (and wider) than advertised, and is wearing man capris. The night turns out to be an atomic bomb of disappointment.

"I spotted you from across the car," he started. "I had to tell you that you have the most beautiful hair."

"There's plenty of fish in the sea" and "on to the next" are colloquialisms that we SHOULD abide by after ill-fated online dates, but why is it that oftentimes, we don't? Well, once you become invested in all the messaging and texting and hoping that lead up to meeting one human, even when it goes spinal-tap painfully, you're more inclined to keep it going (and even go out a second time) just to be sure. It's just, you've already put in so much effort, so you try to convince yourself that maybe it was first-date jitters; maybe you'll want to kiss him next time; maybe on Wednesdays he opts for pants that cover his man ankles.

In comparison, my YOLO date with Paul-5-train was just as abysmal, but I wasn't all that disheartened waving buh-bye at the end. That's because there were zero expectations leading up to it -- it's one of the biggest differences between online dating and, well, "old-school" dating in which your first-ever interaction with your date happens face to face.

My advice? Keep swiping right on happn or Cola Meets Burger (or get on a dating site that requires a substantial profile and your credit card, dammit!), but also say, "yeah, why not?" to the person who asks you out to dinner on mass transit; it makes for a great story and in retrospect for me, put my dating life in perspective.

However, take a raincheck if your suitor is lugging a huge sack and not wearing shoes on the R train.

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Brooke Sager is an NYC-based contributing writer for Thrillist who believes there's something to be said for always leaving your house with your hair done. Give her a follow on Instagram and Twitter: @HIHEELZbrooke.