One smart line of inquiry: Ask 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, as a child, 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 opportunity for flirtation—than typical get-to-know-you chatter.
For more ideas, we asked women for the best questions they’ve ever been asked—or what they wish a guy would ask—on a date. Here are 10 great suggestions:
“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.
“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.
“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 favourite 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.
“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.
“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.
This article originally appeared on Men's Health