Consider popping a few of these questions on your next first date and see where they lead the conversation. What do they wish they could have done differently, if anything? You don’t have to rapid fire interrogate someone, of course, but it can lead to a conversation about their past that’s meaningful but still light. This isn’t meant to prompt a confession of your date’s failures. What about you, what do you wish you were better at?
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.
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?
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.
“This will give you a glimpse into their childhood and upbringing.” The thing to remember here is that no one gets to pick the family their born into (or um, wouldn’t you have picked Queen Elizabeth as your grandma?
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“By the end of the date, you want to be able to know if you connect with the person and whether or not you share similar lifestyles and values.
“Asking great questions on a date can give you a lot of insight about the person sitting across from you,” Sarah Patt, matchmaker and dating expert tells Bustle.
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