15 Key Questions to Ask Your Boyfriend – Unlock His Heart and Mind

Do you yearn to know more about the man you love? Is it sometimes hard to know exactly where you stand with him? You might intuitively sense that pressing him in a blunt or forceful way will only backfire on you, creating resistance and distance instead of connection and intimacy.

Here are our sweet fifteen questions to ask your boyfriend that will encourage him to reveal his deepest, most authentic self. Decode the inner dreams and learn more about the unique character traits of your guy by asking some inviting, but not intrusive, questions. Hopefully, what you discover about him will encourage you to love and trust him even more!

1) What was one of the happiest days of your childhood?

This is one of the most important and fun questions to ask your boyfriend about your relationship. If your guy shares a sports victory, you’ll get a glimpse of his inner competitor. If his favorite memory involves warm times with friends or family, you’ll learn how much importance he places on close, intimate relationships. If bringing home straight “A”s was his highlight, you’ll know that he takes great pride in his mental abilities.

2) How do you know that you’re loved?

Here’s your clue to your boyfriend’s primary “love language.” Does he like to hear how much you care about him in words, or does he prefer that you show him by doing helpful things for him? Does he cherish quality one-on-one time with you, or does he go nuts when you buy him a gift? Does he feel most loved when you reach for his hand, rub his back, or offer him a tight embrace? Learn his primary love language and speak to him often in a way he’ll hear loud and clear.

3) How would you spend your last day on earth?

This question zeros you right in on your honey’s priorities. Would he scale a mountain? Grill up a massive steak and drink up his wine cellar? Spend it in bed with you? This question shows you exactly what’s most rewarding and fulfilling about his life. If you pay close attention to his answer, you can help him bring more of these experiences into his daily life so that he associates your presence with fulfillment.

4) What’s your idea of the perfect meal?

Once you get the answer to this question, you’ll have that direct route to your boyfriend’s heart that goes right through his stomach! It tells you exactly how he likes to be romanced when it’s your turn to design a date for him. A lazy seaside picnic from Subway? A six-course feast in a trendy five-star restaurant? Spicy tacos from a food truck? Food is an aphrodisiac, so best to know precisely which eats turn your man to mush.

5) Do you want kids, and if so, how soon?

If you dream of a family, this is one of the most important questions to ask your boyfriend before you find yourself too deeply in love. Be sure you’re on the same page both about having children, and when to have them. If you want to wait 5 or 10 years and he’s itching to be called “Daddy” by next Christmas, you’ll know that some serious negotiation and clear communication is required so expectations are in the open.

6) How do you feel about animals?

If you can’t imagine a home without a few cats lounging on the furniture but don’t care much for dogs, and he sleeps with his Great Dane…best to learn this all up front so that you don’t end up on some “It’s the Pet or Me” reality show!

7) Do you need a lot of alone time?

Introverts and extroverts can make a great team when paired up, but the couples that make this work know exactly what they are getting into from the start. If you thrive on the constant company of family and friends and come alive in a crowd, while he requires extended periods of silence and solitude to stay balanced, best to know this early in your relationship so you can learn to compromise over how much time you spend with others as a couple.

8) Do you think we should communicate every day?

Here again, introverts will typically hate the telephone and shy away from multiple communication demands on their daily time and energy. It’s not you! It’s just how they are wired. But if you equate “love” with “lots of connecting and daily communicating,” if only in the form of a quick text or email to say, “Thinking about you, Sweetie,” make this clear up front.

9) Are your parents healthy and happy?

This question is a great way to learn two important things: Are there are any scary hereditary diseases in his family? What kind of marriage did his parents model for him?

10) If you could change one thing about your appearance, what would it be?

Here’s a direct line right into your boyfriend’s self-confidence! The answer he shares gives you keen insight into his most vulnerable and fragile parts of self. This can help you make a special point of boosting his confidence in those areas of perceived lack. He might say: “I’m too short,” to which you can reply: “You are the perfect height for me!”

11) Describe your dream vacation.

OK, this might actually be, “Where are we going on our honeymoon?” but you’re going for subtlety, right? If he answers deer hunting in Oklahoma or backpacking in Yosemite — unless those adventures are your thing too — you’ll know you’ve got some serious work ahead of you when it comes to traveling together. Start out with weekend trips to more refined destinations and build slowly!

12) Do you like to cook and clean?

Fingers crossed for “I love to cook and clean!” in response, but whatever your guy’s reply to this one, you’ll be prepared for the housework sharing discussion. There are a multitude of creative ways around this. Some couples arrange for one to cook while the other does all the dishes. You can split the chores down the middle, you can each do your own laundry, or one of you can be in charge of the interior while the other handles all of the yard and garage clean up. This can be a fun exercise in learning how to give and take so that you each spend less time doing things you really hate to do.

13) One of last questions to ask your boyfriend. Is fidelity important to you?

While you probably already have a good sense of where your boyfriend stands on monogamy, an open and frank discussion about it will help you determine his long-term potential if it’s a crucial issue for you. Regardless of how you swing, so to speak, best to determine early if your values are aligned here.

14) If we have a fight, do you prefer to talk it out till dawn, or walk away and take a break?


How couples fight is just as important as how they love. Highly communicative, more rational partners are often committed to working things out verbally until both feel complete and heard. Other couples can get caught up in the triggered emotional reactivity of it all, and one or both may throw up their hands — or throw in the towel — and walk away to cool off.

Most couples find themselves using both methods, depending on the prevailing mood and the topic of disagreement. Your guy might tell you that he never wants to go to bed angry. Or he might reveal that he can’t think or speak clearly when he’s upset and needs some time alone to cool off. Either way, you’ll know what to expect from him if a heated argument comes your way, which helps you prepare.

15) Where do you want to be in 5 years?

Of course you’re hoping he says “Right next to you,” but this question reveals much about your boyfriend’s motivations and goals. It shows you what he prioritizes the most right now and what he expects will be important to him in the future.

Are his goals something you can support, share in, and really get behind? Do his future dreams leave enough room and time to accommodate your relationship and nurture a family life if that’s what you desire with him?

What were the most revealing/random-but-cute questions you’ve asked your boyfriend to date? Did his answer surprise you? Tell us why!