The Pink Tax Return — Why First Dates Are More About Free Drinks Than Love in Your 20s New York, New York — October 28, 2025
It’s been two months since my whole break up situation went down, and honestly, I’m getting sick of spending every night alone in bed. The apps are worse than ever, once you’ve met someone organically, you can’t go back to Hinge hell.
Luckily, I work in service. Some boy was apparently watching me at work when my coworker so kindly offered to introduce us. He’s sweet and nervous, so I give him my number, partly because it’s been a while, and partly because I just have to get back out there.
Still, I felt kind of anxious to be going out. Which is fair since it’s my first time dating since my most recent breakup. But I’ve also still been entertaining my cheating ex again (I know, I know), and all I can think about is how much he’d lose his mind if he found out I was with someone else.
The First Date Back In The Dating World
Honestly, I had zero expectations going into this date, and I told him that. It was just nice to go out and talk to someone new. You really have to look at yourself differently when you’re introducing yourself again, when you’re explaining who you are outside of who you were with. I went to have a good time, to hang out with someone fun and carefree.
New boy asks if he can take me to ParkGate, a bar right next to Spaniard’s in the West Village. I hit him with the obvious clue: “Could we maybe avoid the West Village?”
And of course, I was right, my ex was at Spaniard’s that night.
We laugh about it, because everyone in New York City has at least one neighborhood or one bar they avoid because of an ex.
This was honestly my biggest takeaway from him that, and the fact that he sometimes wears a satchel. Anyways, after three cranberry mules and about six “this place is so cute” comments, I could kind of tell there were no sparks.
We head to a second bar. After two more drinks, I order us a quesadilla while he’s in the bathroom. We “split it,” but let’s be real I eat five of the six slices unapologetically. He asks to kiss me, I say no, and we part ways at Penn Station.
What First Dates Are Actually For
First dates should be nothing more than seeing if you enjoy someone’s company no pressure. If not, you get free drinks and can always order bar food, nothing pairs a boring date like mozzarella sticks.
I’ll probably text him back; he was very sweet. But the lack of chemistry made it clear, I’m not attracted to him, but it did feel good to be out again.
He also totally icked me out by insinuating a hookup for the second date. We haven’t even kissed yet, and you want me in your apartment ninety minutes outside the city? No, thank you, I have a vibrator for that.
I mean, come on. Maybe that flies in Ohio, but here in New York? Step up your game, boys. There’s men in this city. (Or so I’ve heard.)
