29 Questions to Ask If You Really Want to Get to Know Someone

One of the best parts about dating someone new is learning all the small tiny things that make them them. And maybe it’s a me-thing, but there’s nothing hotter than picking someone’s brain and discussing all sorts of introspective topics—regardless of whether it’s a first date or the sixth.

But raise your hand if you’re totally onboard with the deep convo vibes, just not sure where to start? Because, hi, yup, same. Luckily we’ve assembled a team of dating and relationship experts to give you a hand on what questions you should ask to fully get to know someone you’re romantically interested.

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You may not be too surprised to find that the key is asking open-ended questions. (Obviously avoid anything that could be answered with a yes or no if you want to get a lil deeper). Here’s what experts recommend:

1. Would you consider yourself healed from the past?

This includes whether they’re healed from their past breakup, childhood trauma, a recent conflict at work, etc. “You don’t want to enter a relationship with someone who will project issues of the past onto you that are unrelated to you,” says counselor Sarah E. Williams. “Asking this question can help you determine if they are whole and fully ready to love.”

2. What are your long-term goals?

Pro Tip: This is the super subtle (but actually genius!) way of asking someone what type of relationship they’re looking for. “This question allows you to get a good picture of what they are envisioning for their life and you get to see if a romantic relationship is part of their plan,” says relationship expert Stephania Cruz. “If they don’t mention having a romantic relationship as a goal, you can be more direct and ask them what their current relationship goals are.”

3. What are some of your biggest fears?

This can be as simple as spiders and snakes, or as deep as commitment, loneliness, and/or abandonment. “This question allows individuals to understand their partner’s vulnerabilities and sharing feares will strengthen the foundation of the relationship,” says psychiatrist Leela R. Magavi, MD. “It will also help gain insight into someone’s past and what helped to shape them.”

4. Who do you look up to the most?

In whatever way you want to interpret it, there’s a big difference between looking up to your grandpa versus someone like LeBron James. Whoever they look up to, this question will help “conceptualize the partner’s core values and personality type,” says Dr. Magavi.

5. What’s your love language?

Truly, the MVP of all questions. “This helps individuals identify their partner’s mode of giving and receiving love, which may improve communication and strengthen the relationship,” says Dr. Magavi. So take the quiz yourself to find out which of the five love languages is your strongest: words of affirmation, physical touch, quality time, gifts, or acts of service.

6. Where do you see yourself in five years?

“This question is great because it gives you an idea of that person’s goals and life vision. You can determine if they’re compatible with yours,” says Jonathan Bennett, a relationship expert.

7. What are you excited about most in your life right now?

This question unpacks not only what the other person values, but also lets you glance into your potential compatibility, says Veronica Grant, a love and life coach. There’s no right or wrong answer, but depending on your personality (like you’re a go-getter and they’re happy just coasting through life), this question will take you straight to any potential personality clashes. You can either weed them out, or start a fun convo about what the two of your visions together would look like, says Grant.

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8. Which TV or movie character do you identify with and why?

“I love this question because it breaks the ice and helps paint a picture without anyone getting caught up in their own ego. We are taught to identify ourselves by our jobs, hobbies, and our education (boring!), and this question totally lightens things up a lot,” explains Nancy Ruth Deen, a relationship coach.

9. What did you wish for last, like at your birthday or when throwing a coin into a fountain?

Their answer will let you know what they think is unfulfilled in their life and what they hope for, says Diane Strachowski, PhD, a licensed psychologist and expert on attachment theory. Did they wish for love? Monetary things? A promotion?

10. What happened in your last relationship that led you two to break up?

“If they blame the other person and don’t take responsibility for their own part of it, watch out,” warns Margaret Paul, a relationship expert. Nothing says red flag like a dude with nothing but “crazy” exes. Smh.

11. What is your relationship like with your family?

Not everyone is super close with their family, but depending on how they view their relationship with them, this can tell you a lot. “Sometimes, what’s going on in the family can have a big effect on the relationship,” says Paul.

12. Who did you turn to as a child when you were scared, lonely, hurt?

If they say “no one” and dealt with stressful situations alone, this is a good indicator that this is how they’ll handle current and future stressors now. On the other hand, if they went to their parents all the time for everything, they might need a lot of validation from a partner, explains Strachowski.

13. How do you deal with finances? Do you spend too much or too little?

Sure, combining finances is a step for WAY down the line, but still, it’s worth asking as finances can be a huge issue in relationships, according to Paul. It can also be a good indicator of how they deal with life, in general. Are spontaneous weekend trips to Paris going to be a thing? Or are you guys gonna cook dinner at home more often than not?

14. What are you most proud of and why?

This question lets you see what they value and how they spend their free time, explains Strachowski. Are they most proud of how their city soccer team went 10-0 last year, or do their eyes light up when they talk about the coffee table they built for their apartment last year?

15. What do you do need during periods of stress? Do you call someone to vent? Do you spend time alone to think it through?

How they answer will let you know what they expect from close ones during rough times, whether it be closeness and a shoulder to cry on, or space, explains Strachowski. If you wind up dating and you find that they withdraw from you when they’re lonely, remind yourself of this so you don’t take it personally.

16. Who is your biggest influence and why?

This question can give you insight into a person’s core values, according to Bennett. If they name their single mother for raising them, they value responsibility and family. If they rattle off someone like Woody Allen, you can run.

17. What are your favorite addictions?

By addictions, we mean anything from chocolate to working out or Netflix. “Everyone has some addictions,” says Paul. The question is, are they going to be honest?

18. Are you a neat person or a messy person? Are you an on time person or a late person?

Even if you’re not planning on moving in together or you’re just gonna be BFFs, someone’s baseline definition of “messy” can be super insightful. Are they gonna be pissed if you spread all your makeup out on the counter for a night out, or will you be annoyed if the laundry piles up on a chair for a week? “It’s much easier if you are both neat or both messy, or both on time or late,” Paul adds.

19. Use five words to describe your mother/father, giving examples to support each.

Depending on how they answer, you can gain a lot of info on what they did or didn’t get from their parents and what the admire or look for in a person of the opposite or same sex, according to Strachowski.

20. Do you believe in karma?

“This is a good question to get to know someone, because it shows whether they believe there are consequences to their actions,” says Laurie Berzack, MSW, a relationship expert and dating coach. If a coworker screws them over at work, are they going to stay up for days stewing about how to get revenge, or are they more the type to forgive and forget?

21. What was the scariest moment of your life, and how did you handle it?

This one is interesting because it can open the door to either emotional history or just life stories in general. Was it when they got laid off from their dream job, or was it when they got lost while hiking with friends? How they answer reveals their ability to overcome conflict and challenges, says Berzack.

22. Where is your happy place?

Another open-ended cutie that can segue into good follow-up questions, depending on how they answer. If it’s a physical place like the gym, or that one great hiking spot on their favorite trail, you can talk about those interests. If it’s a more abstract answer like “any time I finish a book that’s so good I immediately flip to the first page and start again,” that’s a good convo starter, too. “This question allows you to learn what the other person truly enjoys in life,” says Bennett. You can also use it to plan for future dates, gift ideas, etc.

23. What makes you cry and why?

“Knowing someone’s soft side is important to know what triggers them. If they don’t cry, they may not be sensitive,” says Strachowski. Again, if you’re sobbing on a movie date in the future and look over to see nothin’ but stoicism on their face, they’re not a heartless robot—they just have a higher cry threshold than you.

24. When is the last time you got really angry, and why?

This can be an unobtrusive way to find out the extent to which your date is trying to control the world around him or her, says Berzack. Plus, it opens the door for some lighthearted hate-bonding, whether it be over little or big things. Was the last time they got fired up because someone cut them off in traffic? Or, when they saw a bunch of people during rush hour refuse to give up their seat to an elderly person?

25. What is your best quality?

“It’s always interesting to see what a person thinks is their best quality. By asking this question, you get insight into how the person views themselves and what they think is an important aspect of who they are,” explains Christopher Ryan Jones, a sex therapist.

26. Which song or artist are you too embarrassed to say you absolutely love right now?

Not only does this give you a chance to potentially geek out over which Taylor Swift album is best (the only correct answer is “Lover,” obviously), but it also shows playfulness and vulnerability, especially if you’ve just met, says Deen.

27. Are you friends with any of your exes?

This question lets you know two important things in one, explains Jones. It gives you insight into their past relationships and how they ended (does everything seem to go up in a huge wreck, or do things end amicably?), and if they are friends, you’ll know now and won’t be surprised if/when they get a text from an ex they’re still close with.

28. Ask them to complete this sentence: “I most enjoy having someone to do ______ with.”

Sometimes, a person’s intentions can be clearly discussed by simply asking them. Strachowski recommends listening closely to see if what they’re seeking aligns with what you can give someone right now. Are they looking for a romantic partner, a best friend, or just a casual movie-buddy?

29. If money wasn’t a factor, what would you be doing with your life right now?

This is a fun one that can tell you a lot about a person and their passions without them feeling too self-conscious about it, explains Deen. Do they want to be directing movies? Working with animals? Traveling the world? Depending on their answer, you’ve also got great banter to go off of afterwards.

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Sex & Relationships – Cosmopolitan
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