What’s the weirdest thing that’s ever happened to you on a date?

Not all dates are success stories. If you’re looking to liven up your dates together, ask about his weirdest experiences. It will also help you know what behaviors to avoid on your dates!

What’s your go-to move when flirting with a girl?

It’s useful to know how a man flirts as it allows you to gauge whether he’s putting the moves on you. If he mentions an ineffective move, don’t be afraid to playfully tease him about it.

What’s the worst pick-up line you’ve ever heard?

Ridiculous pick-up lines are always a great way to get a conversation started. Although they’re rarely effective, you two can take turns offering terrible pick-up lines until you both beg for mercy.

What’s the funniest thing that’s happened to you?

Nothing lightens the mood like a funny story. To get to know each other better, ask him to share the funniest thing that’s ever happened to him. There’s guaranteed to be an excellent story behind it, so listen up!

What was the weirdest punishment your parents gave you when you were growing up?

Whether strange punishments whipped him into shape or not, recounting them is sure to elicit some laughs!

What or who do you think you were in a past life?

If he’s into spirituality and reincarnation, then humor him by asking about his past life. You may just be able to connect the fascinating dots and become a believer yourself.

Who’s your favorite comedian?

Nothing raises your spirits like some good belly laughs. If you find out who his favorite comedian is, you can schedule comedy date nights and better understand his unique sense of humor.

Have you ever been asked to leave a public place?

Being kicked out of an establishment can be embarrassing and there’s usually a funny story that goes along with the event. Whether he was booted out for being too drunk or simply tried too hard to pet a stranger’s dog, this question is sure to give you a look at his wild side.