Jenny

The guy: Jay

Jenny is 32 and single, and makes jokes that she’s middle-aged and doesn’t date. Her jokes are funny, which is evidence enough that she’s young and cute, and doesn’t have a problem getting asked out. If she wasn’t, her jokes would be awkward and make everyone feel uncomfortable.

For the majority of her post-adolescent life, Jenny was one of those girls with the boyfriend “she’s been going out with forever and is going to marry.” Until they broke up, seven and a half years into their relationship. It happened in the front seat a packed U-Haul van, parked on the street in front of her apartment in Philadelphia, right before they were going to set sail for San Francisco to start their joint life together. After putting the key in the ignition, Jenny’s boyfriend hesitated and then told her that he’s terrified. The van was continuously, annoyingly beeping, reminding the couple to just start the engine and GO already. They didn’t. And it was over.

At 28, Jenny was living a real-life romantic comedy. Well, just the obligatory beginning-sad-part. If her life were a movie, this is what would happen next- It’s dark outside now because Jenny’s been crying for hours alone in the driver’s seat. A ambiguously ethnic delivery man knocks on the door and with a heavy accent asks, “Ma’am, are you OK?” He offers her the classic Chinese take-out box filled with Lo Mein, which she reluctantly accepts and then eats while she continues to cry. Noodles fall from her mouth, agape each time she sobs.

What happens in real life: Jenny screams and curses a lot, and then goes back to her parents’ house where she orders, and pays for, Chinese food, packaged in a more-practical yet less-charming plastic container, which she eats while sobbing in their basement. Her temporary home until she can find a new job.

Just four weeks later, Jenny decides to leave Phili, a city riddled with reminders of her ex-boyfriend, for New York City, the City of Love. No? That’s Paris. Damn.

In Manhattan, unfortunately, it’s very hard for a woman to find love. The ratio of single men to women is nearly 2:1. And when you’re single and in your early thirties, this ratio feels like 10:1. Maybe it is.

Now, when Jenny goes out to bars and meets guys, she usually finds herself having pleasant conversations with married men, and then later, flirtatious exchanges with the falafel guy stationed on the corner near her apartment building to compensate.

Jenny is cool and pretty, successful and independent. But even the coolest and prettiest, most successful and independent girl need some dating assistance with these sucky ratios. So, Jenny decides to sign up for OK Cupid, unknowledgeable that this is typically not an online dating platform for those who are serious about finding a relationship.

It’s her first foray into online dating. Girl’s got a lot to learn.

Jenny “swipes right” when sees a guy named Jay, who looks extremely handsome and polished in his picture. Perhaps too handsome and polished, as if he’s a J.Crew catalogue model. Later that day, she gets a message from Jay, cutting straight to chase. He writes, “You look cute. What’s your number?” Though skeptical, Jenny decides to put herself out there and go with it. She sends him her number and he texts her later that same day.

His texts are whack, but Jenny, who is trying not to retreat from being “out there,” plays along as best she can. Until she can’t any longer.

Jenny confidently infers from their exchange that Jay is a dumb cat-fishing perv. Clearly, he took a took a screenshot from J.Crew.com and made it his default and clearly, he is somewhat illiterate. Hey, if it walks like a duck, quacks likes a duck, looks likes like a duck, it must be a dumb cat-fishing perv, right?

Personally, I love that she tried to get him to send her a dick pic, for no reason other than to see if he would do it. I also love that she changed his name to “Perv.”

Anyways, in the end, Jenny had yet another dating mishap, this time about online dating for the first time, and continues to make jokes that she’s middle-aged and doesn’t date. We’re still laughing.

If this were the romantic comedy version of her life, I’d say we’re nearing the middle part now, where her dating-bad-luck-streak ends and she finds her Freddie Prince Junior. This isn’t to say there won’t be any more funny dating stories down the road, about which I’ll be very excited to hear, and then document on this blog in exhaustive and probably embarrassing detail.