You’ve got all dressed up, sent the “I’m on my way!” message and remembered to take your keys. You’re good to go! Except… what do you say when you finally meet face-to-face?

It’s scary talking to someone new for the first time, especially when you’re trying establish a more meaningful connection. Everyone wants to get to the point where the conversation is flowing as easily as the wine – but getting there can be a challenge!

Well, fear no more, Match is here to provide you with 20 questions to ask a guy you like. For maximum fun, we’d advise starting a question game so you can both get to know each other a little bit more.

Don’t forget that the aim is to get to know one another, not interrogate someone and scare them off – so keep things lighthearted!

The first meeting:

After you’ve been messaging – whether that’s for a few hours or a few weeks – it can feel like there’s no more questions in your ask, or your date might be so beautiful in person that you forget what to say! Well, here’s a few first questions to ask a guy whether you’re meeting for the first time or just starting to talk:

1. “What would you cook on a date?”

Everyone loves a man who can cook, so you should definitely try and gauge his expertise as soon as you can. Finding out what he loves to cook allows you to compare taste buds and work out if you’d live in foodie harmony or constantly be at war over whether you should go out for pizza or mezze.

2. “Are you close to your parents/mum?”

Family is a hugely important part of most people’s lives, so you should try and find out what kind of relationship the guy you’re dating has with his. Don’t pass judgement, but it might help you develop a deeper understanding of why he is the way he is. It’s also important to be careful, especially if they don’t have a great relationship with their parents. It can be a real sore spot so just remember to be sensitive!

3. “What expectations do you have of yourself?”

You don’t have to be all serious, so maybe phrase this one in a more casual way such as: “Ah, so you like music, would you ever learn an instrument? Which one?”. Asking about their view of themselves can help you gain an understanding of how they want to be, what they like and even maybe what kind of relationship they might be looking for.

4. “What do you expect of someone else?”

A direct way of figuring out whether you’re compatible! Setting out your expectations and theirs, it opens up the communication right from the start. You can tell if someone is looking for something really special or just a hookup (and they can say the same for you). Remember that if they ask this one back, honesty is the best policy.

5.“Do you have any pets?”

Who doesn’t like a fluffy addition to their lives?! If you’re an animal lover, you’ll want to find out whether your date shares your love for all things cute and fuzzy. The ability to look after a pet usually shows that he’s responsible and loving – an added bonus.

6. “Tell me about your best friend.”

Watch his face light up as he tells you about his best buddy who he’s known since the age of two. This conversation starter will help you both to relax as you’ll be talking about something familiar and comforting. It can also shed some light on the kind of people your date socialises with, which is a key part of getting to know someone better.

7. “If you ran into the Prime Minister in a lift, what would you say”?

Politics is important. Asking a guy some questions about his political opinion without being too straight faced is a less pressured way to see if your political opinions align – or if you’re willing to see things from their perspective. It can be a controversial one, so be fully prepared to listen and understand where they’re coming from, never judge too quickly.

What’s something guys like to be asked?:

When you’re dating, it can feel like rinse and repeat to be asked the same questions over and over again and there’s a tendency for men especially to get quieter as things fall into the same pattern. So, what exactly do guys want to be asked? We’ve put in the work so you don’t have to! Here’s a few examples of how to get a guy talking:

8. “Which movie or song would describe your life right now?”

Keep it fun – and if you’re lucky you might even get a serenade. This is a good question to ask a guy because it gives you a little insight into his current internal world and their preference for film and music. Top tip: make an effort to stay away from any guy who says his life is like a film with misogynistic or problematic themes, although there are some exceptions to this rule, it’s never a good sign if they like films that depict women as less (even if they don’t date women).

9. “Would you ever get naked in public?”

A chance for a laugh together! Asking a guy this question will let you see if he’s up for fun and how open he is. Being naked quite literally translates to being vulnerable (and getting arrested), so it’s enlightening to see how comfortable they are with their own body. Plus, now they’re thinking about you naked by default – double bonus.

10. “What’s the coolest thing you’ve ever done?”

What’s more fun than talking about something cool you’ve done in the past?! This question allows you to get to know what they think is cool and out there and lets you into their perspective a little more – plus you could discover what they get up to in their spare time.

11. “What are the three best things about you?”

Guys love being asked this question as it gives them a chance to brag a little (or a lot). And you’ll be able to tell a lot about their personality based on the answers they give! You could also ask about their three worst characteristics which is bound to bring out some entertaining answers.

12. “What’s the first album you bought/the first gig you went to?”

The answer to this question is likely to be either exceptionally cheesy (Britney Spears’ – “Oops!… I Did It Again” and Steps in my case) or fairly cool. A guy’s response to this question and whether they give you a seemingly honest answer can be really telling.

13. “What’s something you’ve always wanted to do but haven’t yet?”

A subtle way of asking about the future – you can see what someone’s ambitions are and perhaps even some of the wilder sides of your date! Asking a guy this question is also a good opportunity to be a bit of cheeky fun with your date too.

14. “What’s your biggest guilty pleasure?”

It’s a good idea to leave this question open-ended, so you can hopefully get an answer about something unique and interesting. This starter can lead to endless conversation topics and helps people to open up by sharing things they would normally keep on the down-low.

And finally, a few no-nos which you should generally avoid in the early stages of dating:

Finally, here are some questions NOT to ask on a date – as intriguing as they may be. Some can come across as rude and a few can be too soon to ask in the first few meetings, you might get there eventually but for now it’s best to leave these out…

15. “How many people have you slept with in the last week/month?”

You might not like the answer to this question! The thought of someone you want to date sleeping with someone or multiple people recently can be really off-putting. There’s nothing wrong with having an active love life but asking about timescales makes everything seem more vivid.

16. “How much do you earn?”

Money can be a super-sensitive subject, even after months of dating. Many people feel uncomfortable discussing their salary so you should definitely avoid asking about specifics. Likewise, someone gloating about how much they earn can be a huge turn-off.

17. “Do you want to get married/have kids?”

This one is debatable as it can be a relief to get it out of the way and check whether your views align. You should probably avoid asking this directly this during your first few dates and keep things light and exciting, rather than planning your next 50 years together on the first date.

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18. “When was the last time you cried?”

Is this the oldest and most overused date question ever? Probably. It’s definitely not the best way to find out about someone’s feelings and more than likely you’ll get a response somewhere along the lines of “I watched a video of a sad puppy” (this is known as a softboy answer, the softboy being a particular genre of guy who appears to be more in touch with his feelings, but really it’s all a ploy to get what they want from someone) or “I was chopping onions last week I think…” (rubbish answer). It really tells you nothing about the person so it’s best to stick to more open and perhaps unexpected questions to start with.

19. “Sooo… what are we?”

Stay away from this one early on! It can help later on to talk about boundaries and what you want, but for the first few months it’s best to just enjoy yourself. Being overly direct can scare people away (even though it shouldn’t). Instead of asking “what are we?”, try setting out what you’d like by instead saying: “I’m tired of the hookups! I want something real with someone.” It’s less confrontational and keeps the conversation on your terms rather than bombarding someone else with an intense question. Remember: go with the flow and not try to put too much pressure on someone – even if you really, really like them.

20. “You expect me to pay half of the bill?!”

It’s 2021, of course you should offer to split the bill. If the other person insists on paying, that’s fine. But expecting someone to provide for you financially isn’t on the menu anymore – and even if you’d like the other person to pay the bill, don’t exclaim your distaste when they say they don’t want to!

What else are you waiting for?

Now it’s time for you to put these questions into practise!

Asking a succession of personal questions could make the person you’re dating feel a little interrogated, so remember to keep things light hearted and don’t ask anything which might seem intrusive or nosey – you’ll learn everything about them in due time if you’re supposed to. Also, asking someone five or six questions in a row isn’t advisable either; instead, intersperse your conversation throughout an evening or daytime so your approach to these topics will things feel more natural. Remember, having a script for a date isn’t the way to go about getting to know someone! Try not to overthink everything and go with the flow – when the conversation is flowing easily, asking these questions will probably be the last thing on your mind.

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