How To Play 21 Questions With A Guy To See If He’s Right For You

These days, dating is at the mercy of our ever-shortening attention spans. Apps present us with a never-ending stream of options, making it impossible not to wonder whether the perfect person is just a few swipes away. But if you actually want to find the right person for you, stop swiping and start asking him about things that matter. While you’re not trying to put him through a job interview, why not play 21 questions with this guy to figure out whether you have relationship potential?

How to play 21 Questions with a guy

“21 Questions” is a game where one person thinks of an object, person, place, or thing, and others try to guess what it is by asking yes-or-no questions. The goal is to figure out what the person is thinking of in 21 questions or less. However, we’re turning the game on its head here. In this version, you ask a guy about 21 different things in his life. The topics you discuss can be as varied as you’d like. In fact, the more out there, the better. By giving yourself a limit of 21 questions to ask him, you get down to the nitty-gritty. If you use your “turn” wisely enough, you can find out just how compatible you are.

Of course, you should be willing to answer questions from him in return. He may decide to ask you the same questions in return. Or, he might come up with his own. Either way, this is a great ice breaker. You’re guaranteed to feel much closer to him when the game is done. Plus, you’ll know way more about him than you did before you started. Chances are, these things never would have come up naturally.

What to ask about when playing 21 Questions

couple having conversation on couchiStock/Morsa Images
Cheerful couple looking at each other. Happy man and woman sitting by couch in living room. They are spending leisure time at home.
  1. His relationship philosophy What does he think a relationship should provide? Stability? Excitement? Evolution? Your relationship needs should be aligned if you decide to get serious. Better yet, you can find out if he wants a relationship at all. If he’d rather keep things casual, that tells you all you need to know.
  2. Kids Deciding whether or not to have kids is inevitable and irrevocable. Once you actually start a family or go through menopause, you can’t change your mind. Being on the same page with your long-term partner on what you want is crucial.
  3. How he spends his disposable income Everyone has a guilty pleasure that they like to splurge on, whether it’s cars or skincare. Make sure his isn’t a dealbreaker for you. If you’re going to play 21 questions with the guy, really pay attention to his answer to this one because it tells you a lot about his approach to finances.
  4. Adventurousness You need to know that when it comes to stepping outside your comfort zone, you have similar definitions of excitement. If you’re an adrenaline junky, you probably don’t want to go out with a homebody who hates the outdoors.
  5. How he expresses love Learning how he gives love will help you imagine what it would be like to be his partner. If your need for love matches his way of giving love, you might make the perfect couple.
  6. Where he sees himself in five years His life goals should fit with yours. They don’t have to be identical — everyone’s ambitions change when they’re in a relationship — but they shouldn’t be wildly different.
  7. His hobbies You don’t need to share everything, but you need to respect each other’s passions. If you’re a vegan animal rights activist and the guy you’re dating is a lifelong hunter, you probably won’t be happy together. Make sure there’s at least a little bit of overlap there.
  8. His relationship history You don’t want a guy who badmouths his exes and has a string of messy breakups. We all have skeletons in the closet when it comes to our love lives, but beware of any red flags he starts waving on this one.
  9. His ideal partner Make sure that what you have to offer aligns with what he’s looking for. You don’t want to end up feeling pressured to be someone you’re not.
  10. What he does when he hangs out with his friends A guy may be thoughtful and loving around you, but spend every afternoon getting drunk in strip clubs with his friends. The more you know about his non-romantic relationships, the more you’ll know him.
  11. His choice of career Did he choose his job because he’s passionate about it? Because it pays well? Because it gives him the flexibility to pursue his hobbies? Learning about his professional life will give you insight into what a life with him would look like.
  12. His dealbreakers Not only will this ensure that you’re a good match for him, but it will also give you a sense of his worth. If he says, “ugliness” or “bossiness,” for example, you should leave without splitting the bill.
  13. His relationship with his family Like it or not, being in a serious relationship with a person also means being in a serious relationship with their family. You need to be prepared for any unpleasant dynamics so you know what you’re getting yourself into.
  14. His relationship with alcohol/drugs Being aware of your partner’s drinking and substance habits will tell you what they’re like in social situations. It’s also important to know whether they have issues with dependency or have a different relationship with health than you do.
  15. His regrets Regrets indirectly reveal a lot about a person’s weaknesses. Do their regrets reflect impatience? Passivity? Shallowness? Is there a pattern? The answer to these questions will help you see the person more clearly.
  16. Political views It is perfectly possible for two people with vastly opposing political views to be madly in love their entire lives, but it is also possible that they will be incompatible. The important thing is to know whether or not you can get past it, and that requires communication.
  17. Marriage Some people dream about a fairytale wedding and a traditional legal partnership. Others think the entire institution is outdated and irrelevant. Either way, marriage is an emotional topic, and sharing similar perspectives on it means that neither of you will be disappointed.
  18. Definition of success Sharing values is one of the most important markers for a couple’s long-term compatibility. Is success defined for him by dollar signs? Family life? Early retirement? The more his answer aligns with yours, the more likely you are to be right for each other.
  19. His social habits While extroverts and introverts frequently make ideal couples, there needs to be a common understanding. You don’t want to be with someone who you never see because they’re either always going out or refusing to leave the house.
  20. His greatest accomplishments The things that make us proud are often surprising. For example, a scientist who discovers the secret to the universe may be proudest of their violin skills or grandchildren. Learning what a guy is most proud of will give you another glimpse of his values.
  21. His weaknesses Self-awareness is important. If he claims that his worst qualities are “loyalty” or “being too loving,” you’ll know he’s being dishonest either with himself or with you.

If you’re going to play 21 questions with a guy, it’s important to note whether he actually listens to those questions and comes up with thoughtful and thorough answers to them so that you actually get to know more about him. If he gets through these questions and you end the game feeling like you have more of an insight into who he is and what he’s all about, that’s a pretty good sign.

Rose Nolan is a writer and editor from Austin, TX who focuses on all things female and fabulous. You can find her geeking out about the latest film releases or stunning crowds with her endless capacity for celebrity trivia. If you can’t find her, she’s probably eating tacos.