42 Questions to Ask a Man Before Dating Him

Break the ice, learn more about the guy you’re dating, and have fun in the process! These are some funny, flirty, random, and personal questions to ask a man before dating. Arm yourself and get ready for your date!

Getting to Know Each Other

Sitcoms have lied to you. There is no theme song to your life, sarcasm isn’t that funny, and, more importantly, men are not simple humans who laugh at fart jokes and only care about football.

Okay, maybe a bit. But there’s more to it than that. The best questions to ask a man before dating don’t revolve around their favourite Nicholas Cage film and which football team they support.

Women might be from Venus and men might be from Mars, but we’re all still human. Everyone feels a little anxious when meeting people for the first time. We all love to talk about our hobbies, and we all love a good laugh.

Keeping these things in mind, these are the best questions to ask a man before dating:

• What do you do for a living?

Not too personal. But a good way to learn more about him.

• What are your goals for the next 5 years?

One of the most helpful questions to ask a man before dating, as you need to think about your future, as well as his.

• How long have you been looking for a partner?

If you met on a dating site, ask him how long he has been looking. And if it’s been a long time, probe him and find out why. Maybe he is too picky. Maybe there are red flags you’re missing. It could also be that he hasn’t had a lot of time to find a partner.

• Do you like to travel?

A keen traveller can make things work with a partner who prefers to stay home, but it will be tough.

• What do you do in your spare time?

You could be sharing hobbies in the near future, so find out what he likes to do.

• If you could choose any profession, what would it be?

When his reality doesn’t align with his dreams, ask why, and make sure it’s not making him bitter and unhappy.

• If you could go back to school, would you take a different career path?

As mentioned above, this is one of the best questions to ask a man before dating, as it tells you how happy he is with his current situation.

• What are your top three all-time movies?

If you find a film that you both love, it becomes an easy topic of conversation when every other conversation runs dry.

• Do you have any special skills that few people know about?

Let him show off. If he can do something without props, ask him to show you what he’s got.

Random Questions

Sometimes, the best questions to ask a man before dating are completely random ones.

A random question shows him that you’re a little quirky and odd—men love that. It’s also a great way to get to know more about a guy, whether you’re digging deep into his family or previous partners (a dangerous line to cross, so be careful!) or discovering his favourite shows, films, people, bands, or hobbies.

You don’t want to probe too much, though, especially if you’re only just getting to know him. Save those deep questions for when you’re actually in a relationship. Otherwise, the red flags will rise, and he’ll run a mile!

• What would your superpower be?

Superpowers and other such topics are good questions to ask a man before dating, as they can disclose hidden anxieties and traits. A lot of introverts choose invisibility, for instance, while those who like to show off and be the centre of attention lean toward strength.

• Do you have many dreams?

Dig deep into those dreams with a Freudian lens to learn about his anxieties and the things he thinks about all day.

• What would you do if you won a million dollars?

He might answer by saying he will give it to charity, so keep pushing if he does. Is he spending it all on cars and homes or holidays and experiences?

• If you could travel back in time, what era would you visit, and what would you do?

What time most interests him? Is he trying to change history or just learn more about certain periods?

• If you could meet any person, past or present, who would it be?

He might go deep and talk about a family member or keep it light and discuss a historic hero.

Funny Questions

Forget about football, beer, action films, and other stereotypes—humour is often the real way to a man’s heart. A little light conversation and a few jokes also help to lighten the mood. You’ll feel more comfortable, and so will he—you’ll be laying some pretty solid foundations.

Here are 6 funny questions to ask a man before dating:

1. Is a Jaffa Cake a biscuit or a cake?
2. If you can have hot cereal and cold soup, are all cereals soups and all soups cereals?
3. If your life was a video game, what cheat codes would you use?
4. What’s the funniest thing that has ever happened to you?
5. What’s your most embarrassing moment?
6. What’s your weirdest habit?

Personal Questions

If you’re already in a relationship, you should feel comfortable asking him whatever is on your mind. Getting to that point can be a little tricky, though.

Nothing kills the mood faster than asking about his ex-partner and getting a long, drab sob story in reply.

Just keep it light. Let him lead. If he clearly isn’t comfortable pursuing a certain topic of conversation, pull back, joke about it, and change the subject.

There will be another day, another date, and a better moment (probably).

When it comes to personal questions to ask a man before dating, you have to use your own judgment. These are not the best topics of conversation for a first date and can be tricky, even on the fourth or fifth date. But it helps if you lay the foundations with some personal things about yourself.

• What do you value the most in life?

It’s okay to be ambitious and obsess over money, but not if you have your sights set on starting a family and having kids.

• Do you want to have a child at some point?

Speaking of having kids, does he actually want to take this step?

• What is your biggest goal in life?

Men want women who will support them in their goals, so show some interest and encouragement to impress them.

• What about me first attracted your attention?

What was the first thing he noticed about you? Did he actually choose you because of something in your profile, or did he just spam everyone and latch onto the first person that responded?

• How do you manage stress and anxiety?

One of the better questions to ask a man before dating, as you’ll get insights into potential red flags.

Flirty Questions

How introverted are you? Are you the first to make a joke and test the boundaries, or do you cringe at yourself every time you make an accidental double entendre?

If it’s the former, you’re going to love these questions. So, let loose, give him both barrels and show him your flirty side!

If it’s the latter, these will not be your favourite questions. But you need to push yourself a little, as many men expect women to be at least a little flirty. They don’t always pick up on the subtle signs. With some men, you can strip down to your underwear, give them “come-to-bed” eyes, and wave an “I want you” sign in front of them, and they still won’t get the hint.

Flirty questions help to set the tone and drop lots of little hints.

Here are some flirty questions to ask a man before dating:

• What do you think about when you’re alone?

It could get kinky, and you could learn something new and intriguing about him. Or you might discover he has an unhealthy fascination for Fortnight or Magic the Gathering. Either way, it’s a learning moment!

• Do you ever make the first move?

You know what to do if he says no.

• What is your favourite thing about me?

You’re pushing for compliments, but it also helps to know what it is that he likes about you.

• What is your first thought when you wake up in the morning?

What is he really thinking? Does he think about sex, food, and football, or is he not a morning person?

• Who was your first-ever crush?

The person will likely not be a part of his life anymore, but this is a perfect question for encouraging him to open up.

• Have you ever been in love?

These are ideal questions to ask a man before dating, as he’ll tell you if he is still holding a candle to an ex-partner.

• What is your love language?

What is the thing that makes him feel warm and fuzzy in a relationship? What does he want and expect from a partner?

Questions to Ask a Guy About Dating and Relationships

This one is all about compatibility. Are you peanut butter and jam or chalk and cheese? Do you clash on important topics and need a mediator every time you choose a restaurant for a dinner date, or do you click on an almost subconscious level?

As noted above, you’re treading thin ice when talking about an ex-partner and can also cross a line when delving too deep into his family life, the people he loves, and the things that make him tick.

Take it slow, pay attention to how he responds. If he’s open and happy, he’ll respond quickly, make eye contact, and tell you everything; if he doesn’t appreciate your question, he’ll be short and abrupt and may try to change the conversation.

• Have you ever cheated on a partner in a relationship?

He might not be honest, but you can often tell from his reaction. Some will openly admit to cheating and then try to justify it, but he could be using the same justifications to cheat on you at some point in the future. It’s a good question to discover if he is Mr Right.

• What important lesson have you learned from previous relationships?

It’s one of the most eye-opening questions to ask a man before dating, as it will tell you how his relationships have helped him to grow. Every coupling teaches us something, whether it’s about ourselves or relationships in general. If he has been with many other partners and has not learned anything, it’s not a great sign.

• Is there anything you regret about a previous coupling?

This could be an eye-opener. If he talks positively about his partner and clearly misses them, you could have a difficult time ahead if you date a man like this. If his answer is that he should have been more attentive or helpful, it’s a positive thing.

• How do you approach conflict in a relationship?

Be wary of anyone who says that arguments are healthy. They’re common, and it’s good to get disagreements out in the open instead of bottling them up. But if he thinks arguments are helpful, even with a new person, there will be a lot of conflict ahead.

• What are your main relationship goals?

Do those relationship goals align with yours? Does he want to have kids or has he decided he never wants children? Is he looking for something long-term or does he just want to have fun?

Questions Men Like to Be Asked

The conversation has devolved into small talk. You’ve gone from asking about best friends, family members, and the things he loves to moaning about the weather and repeating the trite lines that every Brit resorts to when they have nothing else to say:

• “Lovely day today, isn’t it?’
• “What happened to summer?”
• ‘Raining again. It’s supposed to be nice tomorrow, though”.

Don’t be that person. Don’t be those people! You’re on a date. You haven’t bumped into a neighbour while putting your bins out.

You could also find yourself facing a guy who answers every question with a one-word answer, seemingly trying his best to kill the conversation.

In situations like this, it’s time to ask the questions he wants to hear. And if these don’t work, well, do you really need a new boyfriend right now?

• If you could play a sport with any athlete, which sport and athlete would you choose?
• If you run the world, what’s the first policy you would implement?
• Who would play you in a film of your life?
• What’s your greatest attribute?
• What’s your favourite video game?

Conclusion

Good questions to ask a man before dating are ones that will break the ice, ease you into a conversation, and teach you more about them without asking directly. Want to know about his anxieties and regrets? Ask about his job, education, and dreams.

Need to know about his family and exes? Ask him about the things he could change, the things that matter to him the most, and the lessons he has learned.

More importantly, don’t jump from one question to the next. Keep it natural. You’re conversing with him, not interviewing him, so don’t interrogate!

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