Get us in your inbox


TONY readers' worst dates

Think you've had it bad? At least he didn't want to sex up his grandma.

Alex K., 29; aspiring public interest attorney; Ridgewood, Queens

“On a first date with an older woman (I was 27, she was 40), she revealed how her prior marriage collapsed: Her ex-husband pharmacist illegally gave her prescription drugs like OxyContin, which led to heavier drugs like cocaine. An intervention ensued, followed by rehab and a divorce. I’m happy she got help, but it was the worst case of too much information divulged I had ever experienced.”
Can you show Alex a better time? E-mail

Michele D.M, 35; art therapist; Clinton Hill, Brooklyn
“I was on a second date with this lawyer, sitting at the bar, talking about things, life, etc., when he tells me his dream job was to be a singer. My reaction was, 'Oh. Okay. That’s great.’ I thought it ended there. But for the next ten minutes, he sang songs to me while we were sitting at the bar. I was looking around in complete embarrassment, hoping others couldn’t hear. He just went on and on and thought he was really good. I had to change the subject to get him to stop singing!”
Can you show Michele a better time? E-mail

Caitlin R., 31; TV producer; Park Slope, Brooklyn
“On one particularly comical and horrifying occasion, my date admitted to me that when he was a boy, he wanted to have sex with his grandmother. No joke. He claimed that he was pretty sure his grandma—who wasn’t hot or young at the time—wanted to have sex with him too. Why the fuck are you telling me this?!?”
Can you show Caitlin a better time? E-mail

Spencer S., 48, software company owner, Gramercy
“I met this very attractive blond at a singles party and proceeded to go on two dates [with her]. For our second, we grabbed sushi. I was not paying attention when my tuna roll slipped from my chopsticks and soy sauce splattered on my date, who happened to be wearing a bright white jacket. She was covered from waist to face with huge blobs of brown gook. I apologized profusely, helped clean her with my napkin, offered to pay the cleaning bill, and even told her that I would replace the jacket if the stains did not come out. To that she replied, 'Well, you’ll have to take me to Italy, because that is where I bought it!’”
Can you show Spencer a better time? E-mail

Amy G., 37; author, online editor and SEO specialist; Park Slope, Brooklyn
“I went on a date with a guy I met through His photo on the site was ten years old—I almost bolted when I saw him but decided to tough it out. He suggested an afternoon at the American Museum of Natural History, then had the gall to balk at the price. Afterward he told me I was buying lunch. Tacky!”
Can you show Amy a better time? E-mail

Christopher K., 24, account executive for a PR firm, East Village
“I went on a date and all was going well until about five minutes in, when he mentioned his upcoming birthday. I asked what he was doing and he said nothing, so I suggested he plan a nice dinner for one or two friends. Little did I know this would spark an all-night marathon iPhone-debriefing where he picked out friends to invite to a newly planned, massive birthday party. I lasted an hour before I said, 'I can’t take this anymore,’ made him buy me one last glass, and fled.”
Can you show Christopher a better time? E-mail

Jeremy W., 30; internet sales manager; Kew Gardens, Queens
“My account led me to accept a date from a 35-year-old attorney. We met up in front of a coffee shop, said our introductions and headed inside. After a few minutes of first-date small talk, he started looking around, very bothered. 'I don’t like this place,’ he said. 'Do you want to go for a walk instead?’ It was raining, but I decided to go with the flow. We walked around the neighborhood for a few minutes, saw the subway, and he stopped and said, 'Oh. I can get my train home from here. Well, good night.’ He then turned and walked down into the station. I checked my watch.... From start to finish, the entire date lasted 15 minutes. A new record! I guess even 35-year-old attorneys can be immature weirdos.”
Can you show Jeremy a better time? E-mail

Meredith N., 32, counselor, West Village
“I got bamboozled into going on a date with a colleague’s nephew who, unbenowst to me, was 35 years old and still living with his parents on Long Island. In addition to his heckling the waitress, when I told him I didn’t cook, he said, 'Well, you’ll have to learn, right?’ Luckily I caught the eye of a super-cute guy at another table and left a note on his lap: 'I am on the worst date ever—you will have to take me on a better one.’ We dated for nine months.”
Can you show Meredith a better time? E-mail

Piper F., 25; receptionist; Jackson Heights, Queens
“In college, I was on a pseudo blind date with a guy who wanted to hit Taco Bell and a movie. He wouldn’t pay for my 99-cent burrito, and when I brought up my love of horror movies he decided that was the opportune time to discuss how his uncle died. In gory detail. He got so upset, he ended up leaving me at Taco Bell by myself. Let’s just say I didn’t finish my burrito.”
Can you show Piper a better time? E-mail

Erin G., 27, clinical dietitian, Upper East Side “[On one first date, the guy] asked if I wanted to grab another drink. Not realizing we were walking toward his place, I agreed. We entered his studio, I sat on the couch and instead of grabbing drinks, he sat next to me. Within two minutes he was maneuvering my hand toward his private area. I pulled away and he responded, 'Well, if you don’t want to do it, do you mind if I do?’ Then he walked to the bathroom and returned with a wad of toilet paper in one hand, his junk in the other, and proceeded to pleasure himself in front of me!”
Can you show Erin a better time? E-mail

Josh J., 28, math educator, Upper West Side"I placed an ad on Craigslist and began chatting with someone who could put together a coherent sentence. Her e-mailed photos revealed that she was cute, so we agreed to grab some coffee. We met, and not a few seconds into [the date], I realized she had left out a pretty significant detail: She was mute. Literally, she had no voice. We sat and 'chatted' as best we could. Talk about a one-sided conversation." Can you show Josh a better time? E-mail

Luis P., 20, student, Union Square
The Powerpuff Girls
is not a conversation topic for first dates. I know that, you know that, everyone except this one girl—let’s call her Bubbles—knows that. But that night, I learned more about the character Bubbles than the girl herself. Being a nice guy, however, I still walked her back to her place; those 15 minutes turned into a listing of her favorite episodes. When she tried to kiss me, I stopped her and said that I just didn’t think this date went well at all. So what does she do? She kneed me in the groin and went inside. I needed an ice pack for two days afterward!”
Can you show Luis a better time? E-mail

NEXT Sticky-note confessions: The dating files
New Yorkers dish on the person they're with—mid-date—and TONY compares their answers.

Dates for everyone
The best dates for every personality and mood.

    You may also like