One surefire way to ruin a first date is to dominate the conversation, droning on and on about your new app idea, your trip to Lisbon and your dog’s skin condition without ever taking a beat to ask the person sitting across from you anything about them.
We asked women to share the most intrusive question they’ve ever been asked on a first date and, in the process, discovered there’s a bunch of people in the dating pool who need to brush up on their manners ASAP. Use the questions below as a primer on what not to bring up on your next date:
1. “Are you into anal sex?”
“This question was brought up pretty much out of nowhere on a first date when I was around 19 or 20 in a pretty upscale place in New York City. I wasn’t even a sex writer at this point, just a college student at a wine bar she couldn’t afford with a man in his 30s. I’m not saying this question would be OK even if he knew I wrote openly about my sex life, but the context here is even more insane to me.
“We were talking about pretty benign things when the topic of sex came up. He asked me if I was into anal sex and I almost choked on my wine. He then went on to explain that if anal sex weren’t on the table essentially anytime we had sex, it would be a deal-breaker. We hadn’t even kissed and he was talking about anal sex. We did not go out again. He did text me a few days later with this emoji: ‘;)’ to which I did not respond.” ― Gigi Engle, writer and sex coach
2. “How big is it?”
“As a trans woman, finding guys that want to date me is whole other level of difficult. I went on a lunch date with this guy who quickly proved that he was more interested in ‘experimenting’ with me than actually getting to know me by asking the most intrusive question I’ve ever been asked on a date. While I was taking a bite of my burger, he casually asked, ‘How big is it?’ I almost choked at how nonchalantly he asked. It didn’t seem inquisitive, just objectifying.
“I let him know that I wasn’t comfortable answering and asked him how he would feel if I asked him the same thing. He didn’t seem to understand. I regularly ignore similar questions asked on dating apps all the time so I was disappointed I even went on that date. I made sure to tell the waitress to make the bills separate so he didn’t feel like I owed him a single thing.” ― Janelle Villapando
3. “How much money do you make?”
“This question was asked only after 20 minutes of the date starting. We’d barely taken more than three sips of our drinks. It came up after the question, ‘What do you do for work?’ and when I proudly explained that I’m an author and the CEO of my own company, the follow-up question wasn’t, ‘Tell me more about being a badass?’ It was, ‘How much money do you make?’ My response was how much do you think I make? When he laughed and said, ‘I don’t know, not too much.’ I realised that this conversation had an expiration date, and within another 10 minutes, I was already on my way back home.” ― Jen Glantz, author of “Always a Bridesmaid (for Hire)” and host of the “You’re Not Getting Any Younger” podcast
4. “How do you get your hair to look like that?”
“For years, my go-to style has been a really big Afro. I have been natural for almost 10 years and worn the fro during most of that time. I was on a first date and the guy kept looking at me like he wanted to ask something but was not sure how to phrase it. By the time I finally got him to spit it out, I was super frustrated. After he asked about how I got my hair to be in an Afro, he started to rapid-fire question me. Like what products did I use, and how does it feel? And when he finally started to reach out a hand to touch it, I knew we were over before it started. He got a karate chop to the arm that was making a grab for my hair.
“Newsflash dude: You can’t go around feeling up a girl’s hair and expect anything but an abrupt end to our time together. Not only were the questions rude but the almost-touch without permission felt like a violation. I immediately asked for my food to be boxed up and proceeded to tell the guy how rude he was. He fumbled through an apology as I left him right at the table.” ― Valencia Morton, blogger at Millionairess Mama
5. “No, but who are you really?”
“It was the little ‘no’ at the beginning that really made this question intrusive. Right off the bat, he expressed how disinterested he was in small talk, how he wanted to talk about things that actually mattered, like new developments in neuroscience or Elon Musk (which I guess should have been the first red flag). He kept asking me who I was, and then saying, ‘No, that’s not it,’ when I responded. It was presumptuous, rude and most of all, a neg dressed in the lie of getting to know someone better. He finally stopped when I told him I ran a roast account on Instagram where I expose soft boys with massive egos.” ― Lillian of @
6. “What does your daddy do?”
“I’m a happily married lesbian now. But back then I was dating men. We met through mutual friends and were on our first date, a lunch date. I had high hopes. He was handsome, funny, smart and I adored our mutual friend.
“We were hardly into our salads when he, apropos of nothing, asked, ‘What does your daddy do?’ I was in my 20s, in law school for God’s sake. I laughed, sure he was joking. He was not. He simply tilted his head as if to say, ‘Well?’
“‘He’s a rabbi,’ I answered. I might as well have said he was an ax murderer. I’m not sure if the issue was that I was Jewish. Or the assumption was that I must not be from money. Or if he was hoping to land a wife and a job. All I know is, no date has ever ended more quickly.’” ― Jenny Block, writer
7. “Do you have a tough time orgasming?”
“One time I met up with this finance dude that had been asking me to go out for a while. His first question, even before we ordered drinks, was, ‘Do you have a tough time orgasming? You seem like you do.’ He then proceeded to tell me about the last woman he dated and how she never could orgasm before him. He described how he could get her to climax with the use of a Magic Wand massager. After his far-too-descriptive sexual tales with his ex were finally over, he looked at me as if I was going to answer his question. Instead, I took the opportunity to point out that the Magic Wand was what made his ex orgasm and not him. And then left.” — Mara Marek, comedian and host of “The Happy Never After Podcast”
8. “Why are you still single?”
“It seems my dates want to know what the catch is before investing any more time into me. Not only does the question assume there’s something wrong with single people, it ignores the fact that there are two single people on that date (presumably). While it can be meant in a flattering way (‘How is it possible a catch like you could be on the market for so long?’), in practice it’s off-putting and makes women go on the defensive at a time when they should be opening up to a new love interest.” — Jen Ruiz, travel blogger
9. “Is it true that fat women give better head?”
“Dating while fat is somewhere between awful and a full-blown parody. I wasn’t really faced with the ‘fat women give better head’ stereotype until I started actively dating in my early 20s. I would meet seemingly well-adjusted men, but on more than one occasion on the first date, the conversation turned into something sexually explicit.
“There is a fine line between liking bigger women and having a fat-girl fetish. I don’t want to shame anyone for having a fetish. I personally was not interested in that attention. The most intrusive questions I’ve been asked on the first date were sexually explicit questions directly related to how the men perceived me, a fat woman.” — Brianna McDonnell, body-positive fashion blogger
10. “Was that your ex-girlfriend?”
“I was on a date with a girl who is a musician and we went to see my friends’ band play a show at an artist warehouse. Everything was going great and we ended up hooking up at the show. After the show ended, I saw a friend of mine sobbing in the corner and looking very upset. I went over to her and asked if she was OK and I helped her get herself together. On the car ride home, my date asked, ‘Was that your ex-girlfriend?’ I said no, she’s just a friend. She kept asking, ‘Are you sure? She kind of looks like your ex.’
“This is where the question got weird, because we barely know each other, never talked about exes, and the only ex I can think of that my friend might look like is someone I broke up with five years ago. I asked her how she knew what she looked like and she said she got it from my Instagram. This meant that she had to go back years into my feed to find a picture of my ex-girlfriend and remember this specific one, because I have pictures of other girlfriends on my Instagram. I keep a separate private Instagram now.” — Tevy Khou, illustrator
Responses have been lightly edited for length and clarity. 