10 Questions To Ask Him On A First Date (+ 10 That Are Totally OTT)

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10 Questions To Ask Him On A First Date (+ 10 That Are Totally OTT)



Having smooth, flowing conversation on a first date is an important sign that you and your partner are connecting. But, good conversation doesn’t just happen. You have to know what questions to ask and which ones to avoid. Knowing the difference between good and taboo topics can be a bit stressful to navigate, though.

Imagine if the conversation’s going smoothly when, out of the blue, you ask your partner if he wants to get married in the future. Yikes, asking him about his views on marriage can be a little too heavy for a first date. Remember that you probably don’t know each other that well yet, so you don’t want to make your partner feel anxious. On the other hand, asking him about his hobbies, passions, and the places he loves to go is perfect for the first date. These topics really help to make your partner feel more relaxed, while also making the first date much more enjoyable for both of you.

Before you use the first conversation ice breaker that comes to mind, here are 10 questions you should always ask your date, followed by 10 questions that are best avoided because they’re inappropriate and OTT.


20-What Are Your Closest Friends Like?

By asking him about his friends, you not only keep the first-date conversation light and fun, but you get to find out more about him. You’ll see how important his friends are to him and why he’s chosen specific friends to be his best mates. You might also get to gauge if he’s childish, such as if he only has lots of prank-filled stories concerning what he and his friends get up to on the weekend.

If he doesn’t really have much to say about his social circle, that also speaks volumes.

He might battle to connect with others or be too focused on his goals to have friends.

19-What Have You Always Wanted To Try/Do?

Everyone loves to dream, so he’ll enjoy answering this question. It’ll also give you insight into where he’s headed in life. He might show you that he’s very adventurous, such as if he’s always wanted to climb Everest, or he might reveal an ambitious side to himself, such as if he wants to start an eco-friendly business or earn enough money to retire young. Best of all, you’ll see if he’s a big dreamer and it’ll be awesome to witness the spark in his eyes when he allows his imagination to run wild.

18-What Are Your Passions?

Without passions, we’re just zombies! Ask him about what gets him out of bed in the mornings to see what he’s interested in, as well as what he values most in life. This will help you see if you’re on the same page when it comes to the things that make you feel alive. If you both hold the same things as being important to you, then getting into a relationship would make sense on a practical level. You’re bound to have greater happiness than if you’re seeing life in very different ways or getting excited about completely different things.

17-What Are You Proud Of?

Here’s a question that’s both friendly but also quite informative. By asking him what he’s most proud of in life, you can see what’s important to him. Is he proud of having earned a lot of money, of winning a burping competition, or of having an amazing group of friends or loved ones who always support him? The first answer shows that he’s ambitious and maybe materialistic, the second one shows that he’s always up for fun and doesn’t take life too seriously, while the third reveals a guy who knows what really matters in life.

16-What’s Your Relationship Like With Your Folks?

Family is one of the most important things in life. How he feels about the people who raised him can tell you volumes about him, from where he grew up to what he thinks about marriage, and even what issues (if any) he’s carrying into his romantic relationships because of these vital family relationships. Of course, he doesn’t have to go into too much detail about the relationship he has with his folks, but just by telling you a bit about them and if they’re close, you’ll get him to open up a bit more and let you into who he is.

15-How Would People Describe You?

This is an interesting question because it appears to be about what other people think of him, but it actually tells you more about the views and opinions he holds about himself. This question might even make it easier for him to reveal something about his personality to you because it’s not as direct as asking, “How would you describe yourself?” The bonus is that it keeps the first-date conversation nice and light without feeling like your question’s a spotlight on him.

14-What Are You Looking For?

Don’t be afraid to ask this question. It’s very important so that you both know if a second date should be on the cards or not. But interestingly, as Business Insider points out, many people are afraid to ask it.

Without getting too heavy about what you both want from a relationship, learning if the person’s interested in a serious or casual relationship is important.

Otherwise you’re just winging it until the truth comes out on a later date, and it could totally waste your precious time.

13-What Do You Think About Monogamy?

Okay, so you might want to avoid serious topics like marriage and kids, but knowing if the person you’re dating believes in monogamy is very important. There are different ways that different people gain relationship satisfaction. For you, it might be to commit to one person, but for your partner, it might be that they get to date more than one. You don’t want to get serious about them only to discover that they don’t want to be exclusive with, or committed to, their partner.

12-Where Do You Like To Go When Life Is Stressful?

Everyone gets stressed from time to time, and it’s interesting to see how people deal with it. Maybe your partner likes to hit the gym hard when he’s stressed, or he loves to get into his car and drive to the wilderness. Asking this question will help you learn about how he deals with his darkest days, not just his sunniest ones. It gives you a more real and raw view into his mind while showing him that you’re interested in getting to know him on a deeper level.

11-What’s The Last Concert You Went To See?

For many music lovers, sharing taste in music is important, especially on those long road trips! But asking about the bands and artists he likes also gives you insight into what he likes to do in his spare time. If he’s not big on going to concerts, maybe he’d rather do other activities, like go watch movies or read books. This question can help to open up the conversation much more, while helping you both have a fun chat about your likes and dislikes.


10-Do You Want To Get Married?

You might think that since you’re talking about relationship goals and monogamy, you can slot in a question about marriage. But resist the temptation!

Not only does this question put the person in the hot seat, but it also gives them the impression that you’re racing toward the altar.

Slow down a bit. Take your time to learn about the person’s long-term future desires as you get to know them, as this keeps things much more natural.

9-How Many Kids Do You Want To Have In The Future?

Similar to the marriage question, asking him about kids is a big no-no on a first date. It feels too serious and too focused on the future, totally zapping the first-date casualness that you want to achieve on a first date. Think of a first date as a trailer, not the full movie. You want to focus on making it short, sweet, and interesting without going too deep into topics that can feel overwhelming and even stressful. Save the serious stuff for when it’s appropriate , like when you’re in a serious relationship!

8-How Much Money Do You Make?

Woah, asking your date about his income feels really nosy. It can also make it seem like you’re looking for a partner who’s going to help you out financially, which is off-putting and will make him question your intentions.

In the same vein, be wary of a guy who wants to talk about how much money he earns.

He’s clearly trying too hard to impress you with the size of his wallet. Or, as AskMen points out, if he’s penniless, talking about money makes him look pathetic. He might be hinting that you’re going to carry the financial burden in the relationship. Yikes.

7-What Do You Think Of My Outfit?

You should walk into a first date feeling good about yourself. Asking your date what he thinks about your outfit or something else about your appearance can backfire. It might make you seem insecure, unconfident, and like you’re depending too much on other’s opinions of you instead of trusting your own.

Even worse, your date might think you’re trying to fish for compliments, which is a turn off.

Rather wait and see if he compliments how you look instead of trying to tease a compliment out of him. It’ll just mean so much more if it comes from him.

6-Did You Get A Lot Of Matches On The Dating Site?

It’s sometimes really tempting to ask a guy you met on a dating site if he met a lot of other women from online dating. But resist the urge. Asking this question can come across as too nosy and insecure. He might not feel comfortable talking about other women he’s met, or he might not feel confident to tell you that he didn’t get many matches on the site. Enjoy the date you’re on without trying to turn it into a competition against his other potential or past dates.

5-Why Are You Single?

Maybe it really baffles you how such an attractive, interesting guy can be single, but don’t ask him to give you reasons for why he’s not dating anyone. Instead of complimenting him, this can backfire! As Erika Ettin, a dating site founder, tells Business Insider, “This question is a back-handed compliment at its finest, with undertones of, ‘What’s wrong with you?’ or ‘Why does no one else want you?’ [It] immediately puts the person at the receiving end on the defensive, when that person has nothing at all to be defensive about.”

4-Are You Having Fun?

You might feel so comfortable with your date that you want to ask him if he’s having a good time, but this can be annoying. It might make your date feel put on the spot. What if he’s not sure he wants to see you again? He might not feel it’s right to say he’s actually not having that much fun, which means he’d have to lie. But then that can feel like leading you on. Ugh. Prevent such potentially-awkward situations by keeping your question to yourself. If he’s having fun, you’ll know about it soon enough, like when he gets in touch with you to make a second-date plan.

3-Are You Dating Other People?

You might think it’s your right to know if the guy’s dating other women at the same time as he’s dating you, and it is, but there are better ways to get that information instead of asking him this question point blank. It can come across as rude and a bit defensive, honestly. A better example is to keep the question a bit more general, such as by asking him what he’s looking for in a relationship. If he says he just wants to have fun, then it’s clear he’s either hoping to, or already dating, other people.

2-Where Do You See Us Going?

The reason why this question is best avoided on a first date is because it’s way too early for there to even be an “us.” You might’ve just met this person, or maybe you’ve known them for a short while. It’s too soon to get so heavy! Even if you’ve been friends for years before deciding to go on a date, it’s still too early in your romantic relationship to ask this question. It’s pushy, putting too many expectations on someone who’s just testing the waters with you.

1-How Many People Have You Dated In The Past?

Is it really necessary to know how many other women your date has been in relationships with? Maybe if things become more serious between you, it is. But right now, on the first date, it can look too forward to ask him this question. He might fear there’s no good answer. If he tells you he’s dated 10 or more women, you might worry he’s a womanizer. On the other hand, if he tells you that he’s dated a couple or none at all, you might worry he doesn’t have enough dating experience. Your best bet is to forget the past and focus on the present. Start the relationship with a clean slate.

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