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Going for a first date can be pretty intimidating for most people.

Your mind may be overcome with fears and insecurities.

Have you ever been in a serious relationship before?

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If nothing else, you’re bound to get some interesting answers. Maybe it’s about being with their pet dog in the backyard or the smell of their grandmother’s house. The best way to approach it is as a light-hearted thing by offering an example of your own. ” Or, “True fact, I didn’t learn how to tie my shoes until I was in high school.” It’s a way of letting your guard down and laughing at yourself, a very attractive quality, and an invitation for your date to do the same. What things would you save if your apartment were on fire?

Childhood memories are funny things: They reveal a lot about the way you think about the world, and the way you looked at it from a young age. As long as you’ve got a couple years to cushion you from it, it can be a time that’s rich with funny stories and little observations. What’s something you’ve been really proud of lately? Eating that super-hot chili on the “Dare You” menu at the local diner? If you’re going out together, it’s fair to assume that you and your date are both in the dating game. For me, it would be my photo albums and my childhood stuffed animal, but their question will tell you what they could not bear to lose. The goal of dates is to have a good time and figure out if you want to see more of this person.

I believe that because it has become so easy to find, talk to, and meet up with someone, there is little risk involved and therefore less effort to create real connection.

You meet up with someone to make small talk for a few hours hoping to convince them that you are a fascinating, charming person.

Instead, pull your questions from our queue, meant to inspire more riveting conversation while still getting to the meat of who a person is.

Who was he with at the "dinner thing" he had last weekend?

It’s a great way to learn a little bit more about their background and spark a discussion about the way you both grew up. You want to know where someone came from, but it can be a delicate subject. The way that someone saw themselves in high school when they were can say a lot about who they are. Maybe it’s hitting a time goal on a run or learning how to make pesto or finally getting the hang of something at work. If reading is something you’re into, this is a good way of seeing what tastes you share and what interests your date. It’s a good way to take a peek into their ambitions and dreams. It’s a weird one, and it helps to commiserate over it. Hopefully some of these questions will help you on your way.

(Maybe their relationship with one of their parents or siblings isn’t great.) This is a nice way to leave it open-ended, and let your date chat about their family in terms that are as specific or as general as they want. It opens up room to hear about what they value without making your date feel like they’re bragging. And even if books aren’t your thing, you can bond over your thoughts on whether was better over a movie or a book. Maybe they love that they get to try new restaurants and meet new people, but hate that it takes so long to get to know someone.

Secretly, you are hoping to discover the same about them.

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