Intimidating questions to ask your boyfriend

If you didn’t have to worry about money or a job, where would you live in the world? What was the last book that you got so absorbed in that you couldn’t put it down?

You only get 3 words to describe yourself – what are they? Which is better to listen to – your heart or your brain?

And you don’t want to throw a conversation topic out there only to find it can be resolved with a few yes or no answers, or some shrugging and nodding. Whether he’s the furthest thing from an adrenalin junkie or not, would he be jumping out of a plane or bungee jumping off a bridge? What was the most nerve-wracking experience of your life, that ended up turning out okay? It might have developed into a rather larger tale than was originally woven, but hearing a wild tale of hilarity and hi-jinks is sure to be at least mildly amusing.39. Is it comedy-reality show about him and his friends, or a gritty crime drama (with him and his friends)?

You want something that’s going to delve into your very hearts and souls, and bring you closer as a couple and, truly, a pair of human beings. See number one: just try to remember not to use it at an importune moment in the future lest you bring back childhood blushes.4. Everyone has a secret place that they’d love to take a hike to- find out his. If you could play one instrument, what would it be? Is he a make-investments kind of guy or a buy-the-sports-team kind of guy? Even if he’s already got tats, finding out what else he’d have permanently drawn onto his body is always an interesting talking point.18. Whatever high-flying job you and he are both working now, everyone had their secret shame subject when they were enduring those four brutal years.19. If it was a job interview or a prom proposal, find out what really had him squirming- before he came out on top, of course.21. Everyone need their dose of angst as they hit those turbulent years, and some of us hold those albums in the highest esteem-or deepest shame.22. Everyone should have put thought into this at some point.40. Hopefully, it’ll be some shamelessly weird and crazy creation that you’re just going to have to try out at some point.

If you had the power to read someone’s mind, whose would it be?

Whether you’re in a serious long-term relationship or just hooking up for you third date, finding stuff to talk about can be difficult.

If you had to give me a nickname right now on the spot, what would it be? Do you think it’s possible that we met in a previous life?

Basically, does he think that he’s got good financial sense? Click here to take our quick (and shockingly accurate) “Does He Like You” Quiz right now and find out if he likes you… What kind of extra-curricular activities did you do for fun in high school? Which is better: asking for permission or asking for forgiveness? What would you do if you inherited 1 million dollars tomorrow? What’s the most embarrassing moment of your life so far? Where would you rather live – a big house in the suburbs or a tiny apartment in a great location in the city? If you could have any job in the world, what would it be? Ever have any trouble with the law or get arrested? What do you want to have going on in your life in 5 years, or 10, or 15? Which would you rather be, smart or happy, and why? But hey, you’ll also settle for something new and kinda funny. A chance for your boyfriend to rant about how beautiful Jennifer Lawrence is on your behalf? Everyone has had visions of themselves rocking out with their imaginary band and their smash hit single, but not everyone plays the same thing in their fantasies. Bring back either a bunch of disgusted cringes or a browse through local restaurants who might be able to satisfy your cravings. Know for certain either way, and reap hints for your own inevitable windfall.8. What was the last TV show you watched from start to finish? Nail-biting, hair-playing, seat-shifting….everyone has their one bugbear that just makes their teeth grind (which is also totally annoying).27. Have you found suspect CDs hiding at the back of their wardrobe? Reminisce about those lost treasures of childhood that you secretly want to rediscover.29. Everyone has a story about how they defied authority in their teens- whether it was skipping class or jumping curfew, let them atone for their sins.30. There’s always one particularly vivid or strange dream that hangs around the back of your head for months after you’ve woken up, and there must be a screenplay in their somewhere.36. Are they a Frasier buff or a Modern Family aficionado? When they hit the dancefloor, what move to they immediately start rocking out? Fear not, for we have brought a range of questions, both personal and general, and hilarious and must-know. Nothing bonds a couple like cringing over moments that you’d buried at the back of your head, never to be looked at again. Would he be a brooding guitarist or a showy lead man? What was the last film you saw that made you laugh? Everyone secretly has a passion that they know way too much about. Whether he got a peck from a girl in kindergarten or had his first awkward smooch in high school, first kiss stories are usually adorable or super awkward. Whether he’s been keeping up with True Detective or getting down with Hannibal, something about that little box will tempt us all.23. Whether their still together or not, find out if his dream ticket is somewhere in the realm of Nirvana or closer to Fall Out Boy. Bring their secret shame out into the open once and for all.28. What’s the coolest way you’ve ever spent a night out? What’s the strangest way you ever met a close friend? And if so, are they just heading to bed or just jumping out of it? Find out who they secretly relate to, and who they wish they really were.37.

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