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The Best Questions to Ask On a Date

best questions to ask on a date

How to Naturally Get Her to Open Up

Mastering the art of date conversation can take a while, but overall you want to connect as much as possible while you have the chance. Here are some topics of conversation that you can lead the conversation with when things start to go dry or if you just don’t know what to ask her next without sounding like you’re interviewing her for a job.

What She Wanted to Be When She Grew Up

Pretty much everyone had their ideal career mapped out during childhood, and it’s interesting and often funny to discuss. For some people it’s totally off the wall and silly, while other people know from a really young age what they want to do and actually do it. Find out which type she is. This is also a great way to discover how she feels about her current job without directly asking her if she’s happy. Knowing what people’s dreams are is some great insight into their personalities.

What Sort of Pick Up Lines She Gets

This question is particularly helpful if you guys met online and you know that she uses online sites. Women get so much attention from men on dating sites and a lot of it is humorous to completely absurd. Asking her about it can help to break the ice, lighten the mood a bit, and hopefully might even remind her that you’re a total gentleman and not like those other guys at all. She might even spill what she liked about the way you communicated with her, which is good to know whether things end up working out with this girl or not.

The Most Recent Concert That She Attended

Instead of asking questions like what sort of music she likes, ask her what the most recent concert she went to was. (Or even what her first concert was.) It’s going to open up the conversation a lot more than just having her list a music genre or two. Plus, sometimes people feel a little put on the spot with questions like that, but not when there’s an actually story involved in when and why they attended said concert.

Where She Has Traveled (Or Wants to Travel)

When you’ve covered the basics of living arrangements and all that, talking about travel is a great middle ground full of topics to connect over. Maybe you’ve traveled to the same place, desire to go to the same place, or maybe you can tell her all about her dream vacation because you’ve already taken it. Talking about travel is a good way to gauge people’s level of ambition and interest in the world.

What Her Favorite Book Is

Discussing TV and movies is good too, but often times people have a deeper connection to certain books or authors that feels more personal. As they say, you can’t judge a book by it’s cover, and you can’t judge a woman by her appearance either. You might be surprised to hear about some of the book choices that people enjoy. Not to mention, it’s a great way to hear about some new titles to add to your reading list.

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About Kate Ferguson Kate Fergus is a Los Angeles local and freelance writer for a variety of blogs and online magazines. When she's not writing, the UC Davis graduate is focused on pursuits of the entertainment industry, spin class, and hot sauce.

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