Women Reveal the Best Questions They Were Ever Asked on a Date
Don't know what to say over dinner or drinks? Try these fail-proof conversation starters.
So you planned an awesome first date. Now, you just have to figure out what to talk about.
Nothing gets the sparks flying on a first 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 women for the best questions they’ve ever been asked—or what they wish a guy would ask—on a date. We also combed Reddit—home to many interesting relationship stories—for advice on first date conversation starters.
Here are some great questions and conversation starters to pull out on your romantic rendezvous.
“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.
“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 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.
"Would you rather fight a tiger in water or a shark on land? Just disagree with whatever they say and the conversation will start flowing as you'll have to talk about your personalities to understand your answers to the questions." —Reddit user donutshopsss
"I had a date ask me in a very serious tone, 'So how are you prepared for the Zombie Apocalypse?' And when I had an answer (of course I'm prepared!) he actually laughed and said he wasn't prepared for a genuine response. That led to a very long and fascinating conversation about all skills we feel are necessary to survive in a dystopian society. One of my favorite dates, actually." —Reddit user condimentia
“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.
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