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We Asked 20 Women: What Question(s) Do You Wish a Guy Would Ask You on a First Date?

Want to better your odds of making it to the second date? Listen up.
We Asked 20 Women: What Question(s) Do You Wish a Guy Would Ask You on a First Date?

First dates are stressful—so stressful they can make you wonder why you even wanted to go on one in the first place. (Except then you go to your empty apartment, sit in your boxers watching HBO's latest trending show and remember: Oh, yeah, you're single.)

Luckily, we've sourced experts on everything you need to know on making an exceptional first impression from what to wearwhere to go, and even mapped out what to say (50 total conversation starters!) and—perhaps more importantly—what not to say. But sometimes you want to hear from real women, not experts. Check out what 20 women wish guys would ask them; try them out next time you score a first date.  

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“What my aspirations are. He should be interested in my goals and future without getting too deep or serious since we’re just meeting one another.” - Lisa M. 

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“I like when a guy asks about my family. How you talk about siblings and parents reveal so much about who you are as a person, your relationships, and maturity.” - Cassie R. 

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“I wish guys would dive deeper into questions about my job." - Arielle S. 

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"'When you were a kid, what did you want to be when you grew up?' This shows you what my initial interests were (even if it was ridiculous), gives insight into how I used to be, and how that's differed over the years." - Melanie W.   

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“Ask me about my likes and interests. Everything is usually very surface-level on a first date, so having a guy ask me deeper questions would be a breath of fresh air, and I’d be more interested in return.” - Adriana P. 

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“Ask me anything about my family because they’re my everything.” - Rachel E.

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“What’s most important to you in life? What’s on your bucket list? What things do you hate that guys do? (Oh, and follow that by a promise to never do them.) - Becky E. 

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“What my goals or dreams are in life, or ask what I want to be when I’m older—what my dream job is.” - Tracy G. 

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“Ask what my favorite flower is, and then show up with it at the next date.” - Evelyn L. 

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“For a first date, I love ice breakers and fun games that reveal personality but don’t delve too much into deep waters, like 'Guess who my celebrity doppelgänger is?'" - Gabi Z. 

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“'If you could fly to any city in the U.S. right now, where would it be?' I LOVE the possibilities for branch-off conversations.” - Rena D. 

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“This may seem strange, but ask about my friends. Not right off the bat, but once we’ve covered the bases about me, see how long I’ve known my closest friends. You can tell a lot about a person by their friends and there’s always a lot to talk about.” - Deb S. 

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“I think it’s more than what questions they ask; it’s about them asking questions and actually listening to the responses. You can tell so quickly when someone is just checking off a list of standard questions and not even listening to your replies.” - Brie G. 

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“'Can I get you another drink?’ is the best question to be asked. If the date is going well, she’ll want to stay for another; and if it’s going terribly, she’ll probably need another. And if she turns it down, it'll give you an idea if she's interested.” - Julia W.

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"'Who do you talk to every day?' This question is incredibly telling. Right off the bat you know which friend and family member I'm closest to—the people I trust the most." - Diane L.

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"A guy once asked me what the best date I'd ever been on was. It totally threw me off, but in a good way. We joked about the good and bad ones we've had, the type of experiences and out-of-the-box dates that were a total blast or bust, and then made a second date based on all these mini conversations. It was really clever." - Sasha M.

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"I like when guys throw things like 'What's your guilty pleasure?' or 'What do you like most about the city/town you live in?' or 'What's been the most monumental year of your life thus far?' These questions run the gamut from fun, light-hearted, and serious. Plus, it'll tell you so much about me." - Carissa M. 

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"'What's something I wouldn't guess about you?' No one would ever assume I was in marching band or lived abroad for a year, but these quirky facts tell so much about my life when I was younger—what I learned and where I've been." - Stephanie W. 

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"'What’s the top thing on your bucket list?' This will let you know how adventurous a girl is and if she's open to experiencing some crazy things in life.” - Ashley F.

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"Something like, 'If you were fired right now from your job, what would you pursue instead?' Get me talking about my passions, interests, doubts, and fears. The way this is framed, I can answer seriously or light-heartedly." - Miranda S. 

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