You’re really into a new guy and think he’s pretty great, but you also only know the surface-level stuff about him rather than anything deep and meaningful. It’s time to change that! Here are a few good questions to ask the guy you like to get him out of his shell and tell you more about him.
- What do you want to do with your life? Okay, I know this is a big hitter of a question, but hear me out. Firstly, you can assure yourself you’ll be memorable. It means that, by being bold, you can live long in his memory. The worst thing you can be to a person is forgettable, anyway. Ask the big questions early. It means you can avoid any nasty surprises later on that you waited on asking about.
- What did you have for dinner? This can be your second avenue of approach when the big questions have been asked. It represents a reassuring return to familiar territory. It also means that while you push him outside of his comfort zone in other respects, you also play it safe. Talking with you isn’t an activity that requires him to always be ‘on’ or trying to impress you. He can relax into it too. Therein lies the value.
- What is your favorite animal? For me, it’s penguins. I wrote an article on them when I was eight years old, and it wasn’t good. What it was was cute. That’s what’s important. It means that you can tap into that nostalgic, rose-tinted period in the past when everything was simple and idealized. We should all spend more time with our memories. It makes us all eminently more likable.
- Where did you have the best meal of your life? This is a great avenue for future dates. You’re learning more about his interests and favorite things, and you can place him in a more complex personality. Furthermore, you can attach it to a date night idea. You can either suggest that you go out for the food, or you could even offer to make it for him. Expect to have a RomCom style montage either way.
- What would teenage you be proud of today? This is a really ego-boosting question. It means that you also represent a similarly safe space for him in which he can talk about his hopes and dreams. He can talk about what he feels has gone well or otherwise in his life, and that’s big. It shows you trust each other, and it will blow his mind to be that honest and open.
- What is one of your regrets in life? You don’t have to get too dark too quickly, but sometimes it can feel like a load off when you talk about things that haven’t gone quite right. This is particularly the case when you’re just getting to know someone new. There’s so much focus on performing a great version of yourself so that they’ll like you, but why not cast shadows. Show them that you’re complex and you’re not playing with his head.
- What is your weakness? This might sound like the start of a job interview gone wrong but stay with me. By engaging in this question you can flag up red flags straight away. It might also prompt some reflection on your part just before you commit to a relationship. It serves as a check-in with yourself. It will blow his mind because it’ll be the most healthy thing he will have done in a talking stage.
- How would you describe yourself in five words? This is one of the best questions to ask a guy because it illustrates what he values about himself. Five words isn’t a lot, so what does he think his best and most important qualities are? This tells you so much about him and might even make him realize more about himself too.
- What were you like in school? If it’s been decades since he was in school, chances are he’s very different now than he was then. However, maybe his schoolboy self is still recognizable these days. Maybe he still has a mischievous side that likes to cause a little chaos now and then. Perhaps he was a straight-A student who’s now gone on to get loads of other degrees. Learning what he was like then compared to who he is now is really interesting.
- What’s the best compliment you’ve ever received? He’s probably been complimented loads throughout his life, but which one sticks out above all others? This is another one of those sneakily telling questions to ask a guy because again, the answer will tell you his biggest insecurity or the thing about himself he’s most proud of. If his favorite compliment had to do with his appearance, that’s worth noting. Same for if it was about an accomplishment of his or an innate personality trait.
- If you could see any band or artist in concert, who would it be? It doesn’t matter whether it’s an artist who’s no longer alive and therefore it isn’t possible. Music is such an important part of so many people’s lives, and if that’s true for you, it’d be good to know if you have a lot in common in this department or if your tastes couldn’t be further apart.
- Do you prefer salty or sweet? Maybe he likes a bit of both. This is a more lighthearted question but does sort of shed some light on what kind of snacks he’ll want when you go to the movies next time, right?
- What’s your biggest pet peeve? Does he hate liars? Can he not stand it when someone leaves dirty dishes in the sink? Finding out what really grinds his gears will not only give you some insight into how laid-back or uptight he is but may also serve as a warning if you’re guilty of any of his pet peeves!
- Do you have any tattoos? Would you like one? Maybe you’ve seen his body art because it’s in a visible place on his body. If so, skip this question (though you could always ask if he has plans for more). Otherwise, this question is not just fun to talk about, it’s also a little bit flirty (especially if he has one or more tattoos in a more private place).
- Why do you like me? What a ballsy question. I mean, I’m raising my eyebrows and I’m the one who suggested it. This is the ultimate ‘I’m secure in who I am, tell me who you are’ move. It also shows that you’re confident. There’s nothing quite so attractive as ambition and confidence in a crush. No one wants a shrinking violet. Ask your crush the right questions.
There you have it, a few questions to ask a guy you so that you’ll be on his mind. You’ll find he’s head over heels for you before long.