Cutting the small talk and hitting a guy with some more hardcore questions right off the bat on a first date will make immature losers go running, but the right guy will be totally into having a deep and honest convo. Here are a few things to ask to test the waters, so long as you’re willing to answer them in return:
What kind of relationship are you looking for?
No, it’s not too early to ask this — you’re on a date, presumably with intentions of taking things further, so you might as well get this one out of the way now. Avoid possible confusion later down the line by finding out if he’s looking for a serious relationship or if he’s just looking for a fun hookup. If you’re not on the same page, you’ll know this is the last time you should be seeing each other.
What’s the most important life lesson you’ve learned?
His answer to this question will reveal how he’s dealt with adversity in the past while revealing his ability (or inability) to evolve as a result. Points for him for lessons learned, but definite negative points for an “IDK” answer.
What was the last book you read?
This question has the potential to open the door for a conversation that goes beyond the surface level stuff (if you’re into that kind of thing), or it’ll simply end with a disappointing “I don’t read.” It’s worth a try. If you’re not a reader either, you could substitute books by asking what movie he saw or album he listened to last.
When was the last time you experienced true wonder?
You can gauge a lot about your date’s personality by the answer to this question. If he can’t think of an answer, well, he’s probably not paying attention — that, or he’s not someone who appreciates the little things in life.
What’s the biggest mistake you’ve ever made?
Hindsight is a beautiful thing. If your date can answer this question honestly, that means he’s grown enough to recognize his flaws or mistakes. How he deals with setbacks says a lot about how he deals with life in general. You have to be able to own up to things that have gone wrong if you want to learn and grow from them.
What was your last relationship like?
This will cover how long he’s been single, if there’s a scorned ex lurking in the bushes, or if he was the victim of a horrible breakup and nursing a broken heart. This isn’t an opportunity to rehash every painful detail, but a glimpse into how over it he is, because he definitely needs to be if he’s out dating again.
What’s your biggest hang-up in life?
If you have a guy who is replying to your questions with honest answers, this question will open up additional doors for candid conversation about his past, his childhood and his present mental state — and that’s kind of important.
Do you know your Meyers-Briggs personality type?
I know, I know — this is super dorky, but knowing where he falls on this 16 personality spectrum can provide important insight into the fundamental aspects that make him who he is. If you haven’t yet, find yours out; it’s like having your fortune told. Even if you don’t put too much stock into these things (and you probably shouldn’t), they can sorta be scarily accurate at times…
What’s a pattern that you’ve recognized in past relationships?
This is another searching question that will reveal whether your date’s taken stock of his past or if he just impulsively glides through life without ever looking back. We all tend to gravitate towards certain types of people or behavior patterns, and it’s helpful to be aware of them, whether they’re good or bad.
What do you wish you had more time for?
Priorities, priorities, priorities. We all want more time for SOMEthing, but your date’s answer to this question will provide you with a better grasp on how he actually spends his time on a regular basis.
What do you think happens when we die?
Why waste time waxing poetic about the weather and what you’ve been Netflix binging on when you can get to the meat and potatoes of your date’s belief system? His answer opens up myriad possible conversations on religion, science, ethics, and all the fun stuff you’ve been trying to avoid while sizing him up over his fettuccine.
Can men and women ever just be friends?
This one’s a little loaded: if you end up in a relationship with him and he answers that he doesn’t think men and women can have a platonic relationship, you’ll spend more than a little time questioning his interactions with the opposite sex. At the same time, if he says yes and mentions that he has a lot of female friends, you’ll have to be sure to keep your jealousy in check (which is probably a good thing anyway).
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