12 Awkward Things You’ve Heard on a First Date

We asked, and you told us some of the most awkward things your first dates have said to you. These made the top 12.

Dater 1: She said, “Classical music? What a bore.” Then she spit on the sidewalk. The date lasted 15 minutes.

Dater 2: How about the time she started speaking in the third person in a Borat accent and didn’t stop until I lied and said I had to go back to work (at 10 p.m.)

Dater 3: I’m femme and often assumed straight. So, took a date (ahem, the morning after some funtimes) to a local pub I go to occasionally for lunch. I told her before we went in that I’d been there with two different guy friends in the last couple of weeks and now the waiter would see me with her being all romantic and I was curious to see his reaction. We sit down and the same waiter I’d had both times previously comes over. First thing out of her mouth? “She’s a whore.” Yup, meaning me. The guy hadn’t even said hello yet.


Date: What do you do?

Dater 4: I’m a school librarian.

Date: Oh. I hate reading.

Dater 5: Regarding my opinion of not wanting guns in my house: “Well, if someone broke in, raped you in the ass and left you for dead, wouldn’t you wish you lived in Naperville so I could have automatic assault guns to kill them for you?” (Also her reasoning for moving there since Cook County won’t let her have her guns.) First and last date with that one.

Dater 6: I once had a woman who was an asst. DA downstate go into graphic detail about the man who raped and murdered a child. She then proceeded to tell me how she wanted to have children within the next 18 months.

Dater 7: She said: “I haven’t read any books since high school.” Does that count?”


Dater 8: Went on a date with a woman who claimed she was a witch. Her boyfriend was in jail and she was just looking for someone to “have fun” with and then offered me a glass of water. I didn’t drink especially after taking a tour of her house and she had like five voodoo dolls. I’m good.

Dater 9: She says: “I already have my sperm donor picked out. Would you be into that?”

Dater 10: Then there was the living room furniture all done in pony fur.

Dater 11: Wallet falls open to wicked hot cheesecake shot of recently decamped ex → first date = only date (a blessing, as it turned out).

Dater 12: Technically, to the waiter: “I’d like the veggie burger. With bacon, please.”


What’s the most awkward thing someone’s said to you on a first date? Or maybe you were the one who made it totally weird!