Nothing gets the sparks flying on a date like witty, original questions. Talking about the weather isn’t going to score you any points with a potential romantic partner, so if you’re looking to get her laughing you’re going to have to have to bring your A game.
A good place to start is asking about her job. “People love knowing that you take their work and ambitions seriously,” says psychiatrist Carole Lieberman, M.D.
Another idea: Fire off whimsical questions, like what she wanted to be when she grew up. If that makes her laugh and open up, keep the offbeat questions coming. Unexpected topics can provide more insight into her personality—and opportunities for flirtation—than the typical get-to-know-you chatter.
For more ideas, we asked 20 women for the best questions they’ve ever been asked—or what they wish a guy would ask—on a date.
(Before you can ask questions on a date, you have to choose a good spot. For ideas, check out our list of the Best First Date Ideas.)
“Someone once asked me what my Shark Tank idea would be. (It’s Chipotle, but for Eggs Benedict. I’d call it Arnold.) It was great because it’s unexpected. It’s a fun way to get insight into how someone’s mind works and what they like to think about, and it opens up a conversation rather than ending it.” —Alana R.
“My boyfriend asked me about my ambitions. That turned into a full-blown conversation about what we’re both looking for, not just in relationships, but in life. When that aligns, I find the first dates to be much more successful.” —Viv C.
“The most memorable [question] was when my boyfriend asked me which weird Tinder pickup lines people were using on me, so we both started sharing. It helped break the ice, and then I realized how funny he was. Then when he started asking about my siblings, I knew he was there for more than just a first date.” —Sarah L.
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“He asked me where I saw myself in 5 and 10 years and what goals did I have in mind. He wanted to ensure he was adding to my life and not hindering it. When he asked me to marry him I was sure.” —Jessica W.
“My favorite question to be asked on a first date is about where I love to travel. It opens the conversation up to talk about so many related things, like culture and cuisine.” —Kati S.
“This might sound a little silly, but I would want someone to ask me about my name. Not in the ‘Oh, your name sounds exotic’ way, but sincerely inquiring about the meaning of my name, its origins, and the importance of the name within the family. Maybe it’s too much for a first date, but it holds a lot of significance for me and would show that someone is actually interested—and curious—about who I am.” —Saba A.
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“I ask people if they like pineapple on pizza (I’m a huge advocate). My roommates then both stole it and told their friends, and then I had a man go off at me for asking him about it saying I was unoriginal and to stop getting my opening lines off Reddit.” —Janice H.
“I really liked when one guy asked me for the latest concert I’d been to. It’s much better than ‘What kind of music do you like?’ because that’s just so generic. . . . But the concert question is specific, and then you go from there. You can get into a good story when you have a great opening like that.” —Suzee S.
“I would love if a guy asked me what my all-time favorite book was. It’s a dorky but easy question that shows he is literary! A guy that reads—whether it’s WWII non-fiction or Sci-Fi—shows that he likes to continually learn and expand his depth of knowledge. That’s sexy. Plus, I can launch into a conversation about To Kill A Mockingbird any time, so it’s a great conversation starter!” —Sara A.
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“‘What was your worst job?’ It’s a good one because you’re not talking about your actual job.” —Laura T.
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“‘What’s the first music you purchased?’ So many people just ask what kind of music do you listen to, which can be a hard question to answer.” —Cassandra W.
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“Best opening question was, ‘Fuck, Marry, Kill: Breakfast, Lunch, or Dinner?’ For the record, I went with kill lunch, fuck dinner, and marry breakfast.” —Shawn M.
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“‘What’s the weirdest thing that’s happened to you recently?’ Nothing crazy but it caught me off guard and I had to think about it, which is always good.” —Courtney A.
“One time, someone asked me why I considered myself to be an introvert. I liked that he asked that because it showed that he was really listening to me and trying to understand me as a person. I had been talking about being nervous about networking because I’m introverted, and then I told a story, but he went back to the introvert comment. After that, I knew he was thinking about what I had actually said instead of just waiting to tell his own anecdote.” —Jules C.
“‘If you could jump into a pool of anything, what would it be?’ If a guy asked me a super random question like that, I’d definitely give him points for coming up with it and it would be a fun way to start a conversation.” —Beth D.
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“‘If you was a book, what would be your synopsis?’ It was just a creative way of asking me about myself.” —Dierdra V.
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“On a first date a dude asked me how I would kill myself, which wasn’t particularly sexy but was certainly memorable. He told me how he’d do it and it was so unimaginative I never went out with him again.” — Rebecca F.
*We recommend using this question with caution.
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“The best was definitely, ‘Do you like Richard Greico?’ because OF COURSE I DO. He ended up ghosting me, so [it didn’t work out]. But we’ll always have Grieco!” —Lizz B.
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“I recently got asked, ‘What’s your favorited themed restaurant?’ I thought that was hilarious and had to think about it.” —Sandra R.
“What’s really impressive is when guys ask a niche question. I’m a local government reporter, so I do a lot of stories about boring and jargon-y policy things. I remember one guy asked me specific questions about stormwater management, which I never get to talk about because no one cares. Any guy that cares about the Chesapeake Bay Cleanup Effort is gold.” —Cindy H.
Additional reporting by Sarah Jacobsson Purewal
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