I Told My Date Exactly What Went Wrong & Why I Don't Want To See Them Again

By Ansley Pentz

According to my dating app bio, my greatest strength is eating burritos. If you asked guys I've dated about my best qualities, I hope they'd say that I'm kind, fun, reliable, definitely a little weird. (Oh, and that I’m hilarious, clearly.) The fact that I’m honest and upfront might be thrown in there, too. Blame it on me being a writer or a Gemini — I like talking out what I’m thinking. When it comes to being honest with someone we don’t know well, though, how much of our thoughts about them are they entitled to?

After a recent date that didn't go well (although there were burritos involved), I decided to put that question to the test and tell my suitor why I wasn't into him.

Let me set the stage: I matched with a guy on a dating app in October. I recognized the scene in one of his photos — the greeny-blue of the water in the Roman Baths in England. I used to live in Bath, and I told him so. Our messages were infrequent, and we were absolute sh*t at finding a date to meet. This seems to be a constant theme for me, and perhaps I should be concerned about the patterns I fall into.

We were finally able to secure a time and place, agreeing to meet on the Upper West Side. (We both live in New York.) To be upfront, I deviated from my norm. Rather than arriving relatively on time and sober, I showed up late and a little drunk. I texted an explanation and apology beforehand, along with the request to grab food before pouring back more drinks. I’ll give my date credit where credit’s due: He was understanding and relaxed with my embarrassing buzz.

We found two side-by-side stools in a cramped Mexican restaurant, looking out to the street through the windows. Before I'd even finished eating my food, he had mentioned his ex. I didn’t know how to respond, because I didn’t particularly care to contribute to that part of the conversation.

And then, as if he wanted to crawl into the recesses of my digital past, he asked which other dating apps I was using. I shrugged. This wasn’t the honesty I crave — it was invasive. Why, I thought, was he so interested in my world with other potential dates when he had already secured a seat next to me? As he told me he's only on one app right now, I felt uncomfortable. It's strange to acknowledge all the other people you could be meeting when you're on a date with somebody else.

Still, I continued the date. I’m bad at ending things, and I try to give people a chance, if solely for the fact that a Chance is a fantastic and moving rapper, and everyone deserves a piece of that. This bad date didn’t get any better, though, and instead somersaulted into a progressively more awkward encounter as he drilled me about my music taste and blurted out, "Hmm, what should we talk about now?" It felt like an interview rather than a conversation.

Toward the end of the evening, as he walked me toward my train, I made a joke about the benches in the middle of the road. "Who sits and talks in the median, with the traffic zooming around you?” I wondered aloud. He had sat there once before, he said. With another ex. "Well," he mused, "she wasn’t really an ex." His overeagerness to share was abrasive. I didn’t want to know the intricacies of how he defined relationships with other people. This was a first date! Tell me your favorite color and how good it felt to vote for your favorite candidate. Tell me I’m pretty. Tell me about the scar on your left shin and what shenanigan it’s from. Don’t tell me about your ex-girlfriend.

After the Thanksgiving holiday, I decided to text him how I felt:

Hey! I know this is kinda out of the blue, but thanks for hanging out the other weekend. I just wanted to let you know that a few things you brought up were really off-putting to me, and I think you should know for future dating endeavors. (And you don't have to take my advice!) When you mentioned a couple exes, that was a bit odd to me. It's not like people don't expect you to have a life outside of the person you're currently hanging out with, but it's weird to bring up other people you're dating to the person you're meeting for the first time. Same goes for acknowledging how exactly you're using dating apps. I don't need to know how you're choosing to see other people when I'm sitting right beside you. It's this overly aware kind of recognition that makes the interaction feel forced, like you're checking me off a list of people you've seen. And I know it's weird to receive this now, but I think you should know that for other girls you see. I really hope everything goes well for you. X

Tucked into a coffee shop in Bushwick, I felt shaky, slimy, and afraid that I had hurt his feelings. But it felt refreshing to tell a guy what I really thought about our date, instead of just talking sh*t about him with my friends at brunch. I'll always stand by honesty if it's delivered with kindness.

I waited. I asked the friend whose coffee order mirrors mine if I was too mean, or maybe too honest.

She said that the text was straightforward, but that his actions were off, and he should know. "To bring up an ex on a first date — that’s too much information," she explained. "It’s a complete and total stranger you potentially want to have sex with. You don’t need to overshare in that situation."

I waited.

My friend continued, saying that if someone is so hung up on a previous relationship that they’re bringing this up on a first date, they should talk to someone about it. That someone just shouldn’t be the person they’re sharing the date with.

I waited.

We went to a vintage store.

I waited.

And then, while searching for red cowboy boots, my phone screen lit up. My heart was mid-flutter, mid-sink. I wasn’t sure how the message would be received, and I braced myself for being called a nasty name.

Hey thanks for the feedback. Yeah I got the feeling you didn’t like those things. I’m still getting back into the swing of dating, so mistakes were bound to happen. Hope things go well for you, too.

I was flooded with relief. There’s this weird dance of honesty when you don’t know someone well, and apparently, I had done it well.

When I talked with a few more friends about it, their responses were aligned with what we all say we should be: honest.

One girl who likes guys and girls texted me to say that if she received my message, she’d "be a bit thrown off receiving it but I also appreciate honesty and think I would try to use it to better myself."

A guy who likes girls emailed me to say that if someone weren’t into him, he’d absolutely want to know. "If you’re not into me," he wrote, "why waste time?" But then again, he’s never told someone when he wasn’t into them, because he didn’t want to be mean.

A guy who likes guys talked to me on the phone to say that he would be OK with the text I sent, and he’s let people know when he’s not into them. One time, he hung out with a guy from Grindr who said during the date that he wasn’t into feminine or Asian guys. My friend told him how flawed his ideas of sexual expression and race are, and that is one of the many reasons I admire him.

And so, I don’t feel bad about sending the message. It feels good living up to the identity I’ve created for myself. I am good at both eating burritos and being honest.

Here’s another thing you should know: Right after I sent the text from that coffee shop, "Girls Just Want to Have Fun" started playing. It's so true. With the weight of the message off my shoulders, I felt I could have what I really wanted — some fun.

Check out the entire Gen Why series and other videos on Facebook and the Bustle app across Apple TV, Roku, and Amazon Fire TV.

Check out the “Best of Elite Daily” stream in the Bustle App for more stories just like this!