Question to ask someone on a dating site

It can be hard to figure out what to ask without making it seem like you're interrogating your date.

After all, the key to a good date is relaxed conversation, and the last thing you want is to recreate the beginning of this scene from But whether you're trying to fill an awkward silence or just trying to get to know your date better, we have you covered.

Sometimes (okay, most of the time), though, first dates aren't smooth sailing.

That doesn't always mean you're incompatible — just that we are humans, and dating can be awkward.

First dates can be exciting and awesome, but they can also be nerve-wracking, awkward, and pretty flippin’ weird.

If you’re anything like me, the conversation will invariably turn to boring work stories and how much you’re addicted to guacamole.

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It usually ends up coming up in conversation, but I find myself steering it that way, and then asking when it seems right or normal to."What's your most embarrassing New York City story?

(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.

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"The Big City can be a very weird place whether you live here or have only visited.

This lets me see if the guy takes himself too seriously and is able to laugh at himself.