Whether you’ve been going out for a few months or several years, you always have the chance to learn something new about the man you’re seeing. But you can’t just fold your hands and expect to learn everything naturally. Sometimes, you need to ask specific questions in conversations to help you get closer to him. Here are some fun questions to ask your boyfriend when you’re bored or just want to switch up the conversation a little.
If you won a multi-million dollar lottery, what would you do with the money? Would he travel the world? Quit his job the very next day and retire or keep working for the man? Is he going to chase his secret dreams? Maybe he’s going to buy a house and put the rest of the money in high-yield investments. He might even surprise you by donating a chunk to charity, research, or starting a scholarship fund. Whichever way he leans, you’ll get an idea of his financial profile.
What would success look like for you? Maybe his idea of a life well-lived is having a ton of money, being able to buy private islands, and afford the finest things life has to offer. Or it could be being comfortable, taking care of the people he loves, and making an impact on the world. There’s no right or wrong answer, but it’s a good way to know if your aspirations or values are aligned.
What’s the most embarrassed you’ve ever been? This could lead to an intimate conversation that will either leave you feeling a little sorry for him or shocked by the encounter. You might even find yourselves laughing at the ridiculousness of the situation. You’ll also learn what makes your boyfriend want to retreat into a hole in the ground.
What can you talk about for 2 hours nonstop? This question is a great way to get a peek into your boyfriend’s hobbies and interests. You get to hear some of the things he’s passionate about and is perfectly capable of rambling on about for a long long time if no one stops him.
If money wasn’t a question, what would you do? How he answers this question can tell you a lot about the things he values in life and how he likes to unwind or spend his free time. You could learn what his favorite hobbies are and what he enjoys doing the most.
What are your guilty pleasures? He might be the kind of guy whose guilty pleasure is staying in and playing games all day, the kind who likes to hate-watch crappy TV shows, or the one who enjoys eating some unusual concoction. This question will give you a clue about what he finds comfort in and how compatible you are on that front.
Which movie or book have you lied about seeing or reading? Pretty much everyone has a couple of TV series, movies, and books they pretend to have watched or read. I haven’t read the Harry Potter books, but dozens of people who know me think I have because I have led them to believe this. You can even turn his answer into a couple’s bonding activity by reading that book or watching a movie with him.
If you could have a superpower, what would it be? If you want to keep things light and get him to show you his playful and quirky side, this is a fun question to get him going. Whether he chooses the ability to read minds, move at super-speed, or possess strength, you’ll probably get some lighthearted banter and laughter out of his answer.
What were you like in high school? Was he popular, a misfit, a promising athlete, a drama jock, a huge nerd who loved magic, dungeons and dragons, and fantasy novels? High school is one of the pivotal moments of people’s lives. Knowing what your boyfriend was like back then can help you understand who he used to be and how he became who he is now.
How do you most prefer to spend date night? A guy’s favorite date night activity is a good indicator of what’s important to him. Some prefer a cozy, intimate night in. Others prefer going to fancy restaurants to wine and dine. Some guys live for activity dates so bowling, taking cooking classes, going dancing, anything that keeps them engaged and moving. Depending on his answer you might get some really cool date ideas for the future.
What did you think of me when we first met? Your boyfriend’s initial impression of you might surprise you. He might have noticed something about you that people don’t typically notice or something you get accused of a lot. Whichever he swings, you’ll probably have fun seeing yourself through his eyes.
If you could be a color, what color would you be? Sounds simple enough but maybe his answer might surprise you. Would he be dark and brooding like the color black or bright and cheery like the color pink? It’s easy to assume what his choice would be, but it’s more fun to ask as you never know!
What kind of conspiracy theory can you make up on the fly? This is definitely one of the most fun questions to ask your boyfriend. If he’s a big true crime fan or pores over thriller novels, this question will surely get his attention. Just prepare yourself for a possibly long answer that might be hard to follow.
What’s the funniest story someone has drunkenly told you? Whether he went to college or hangs out with his buddies at the bar, we’re sure he has some hilarious stories about what went on during those moments. If he can’t think of any, you can ask if any strangers have told him funny or random things.
If any animal could be your pet, what would you choose and why? Get his imagination going beyond just dogs and cats and their bigger relatives. Would he want a dragon? How about a shark? Maybe he’d want a unicorn instead.
You’re on a desert island and can only take five movies with you, what would they be? Of course, let him know there is some magical TV there with the ability to stream movies if he thinks too logically. You’ll also get a better idea of his movie/TV preferences.
What’s your go-to dad joke? You can also substitute dad joke for pickup line or knock-knock joke. Depending on his answer, you can look up jokes or pickup lines to gauge his reaction to them.
If you changed your name, what’s the most epic name you could choose? This question’s not meant to be serious so you can probe him with answers. Ask if he’d choose names like “Super Awesome Dude” or “Ultimate Party.”
How curious are you? Get to know him a little bit better by asking this question. You’ll learn his level of curiosity and what kind of subjects he’s interested in learning more about.
What movie best resembles your life? Depending on his response, you two could watch the movie together. From there, see if it matches his given answer.
What song always puts you in a good mood? He could name a single song or if he has a playlist ready, ask to give a listen. You two can listen to the song or songs together as a way of deepening your connection.
If you don’t hear music, would you dance anyway? This question is an interesting one to ask in terms of knowing his level of shyness. Is he not afraid of looking stupid in public? Would he think of it as an opportunity to be spontaneously romantic?
As a kid, what did you imagine adulthood to be like? Growing up, we all have had different ideas about things adults do. You can also ask him how it compares to his life now given his answer.
What’s your go-to karaoke song? If he doesn’t or never did karaoke in his life, you can ask his favorite song he knows all the lyrics to. And if you think he’s willing, ask him to give you a little performance of it.
Ice cream or milkshake? You never know, this could be a make-or-break decision for your relationship.. .just kidding! It’s a fun question that may not have an obvious answer to it. Technically speaking, milkshakes are kinda just ice cream blended with milk, but don’t let him off easy with this one!
What is your most useless skill? Maybe he cleans a fish tank really well or can recite all the presidents in order. It should be something that holds no marketable or monetary value. You can also replace useless skills with a hidden talent but follow the same criteria.
What was the worst job you ever had? This isn’t to ruminate on bad memories but rather find the fun in them. He might have a funny story or two to go along with it. Hopefully he’s not still in his worst job now!
What would you do if you were stuck in the mall overnight? Would he visit all the stores and try on expensive clothes or freak out and try to escape? Would he hit up the mattress store and just have a cozy night’s sleep on one of those memory foam beds? This is definitely one of the most fun questions to ask your boyfriend and would probably be the most fun to experience in real life as well!
What’s the worst purchase you’ve made? In the days of online ordering and shipping, there’s bound to be a story where he bought something different than advertised or can’t remember why he wanted an item in the first place.