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17 questions to ask a boy you’re dating

photo of Tora
by Tora match.com blogger
17 questions to ask a boy you’re dating

Us women are keen to show an interest in the men we meet on dating sites, but how do we avoid leading them down the rabbit hole into a never ending spiral of chat about football, games and hot girls? We spoke to single guys and girls out there to put together a comprehensive list of questions to ask a boy you’re dating – and what not to.

What women should ask men on a date:

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 boy 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.

3. “Have you ever been attracted to a man?

This is slightly left field, but the reaction of the guy you’re dating to this question will be telling. You should be able to gauge how honest and open-minded he is straight away.

4. “Do you have any pets?”

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 – something you’re probably looking for.

5. “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 2. This conversation starter will help you both to relax as you’ll be talking about something familiar and comforting. If things go well you’ll probably be meeting this best friend pretty soon so it’s useful to get some info in advance.

6. “Where do you see yourself in 10 years?”

This is a fairly subtle way of working out what your date wants from the future and what you can expect if things go well between the two of you. If he wants to be living in New York within 2 years and you see yourself settling in rural Cumbria at the earliest opportunity, you might want to rethink the feasibility of the relationship.

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

This is another great question to check how honest he’s willing to be with you. If he’s beating around the bush and claiming it was when he ate a whole ghost pepper a few weeks ago this might show that he’s not particularly in touch with his emotions and is afraid of showing vulnerability.

What men want to be asked on a date:

1. “What sports do you play/watch?”

Whether he’s into Greco-Roman wrestling or football, sports are often a big part of a guy’s life, and he’ll feel proud sharing his passions with you. It’s a great way to start the conversation about how he spends his time. Definitely feel free to change the subject if you’ve been listening to a story about Liverpool’s 2005 Champions League performance for five minutes too long though.

2. “What’s your ideal car? Why?”

Loads of men are into cars, and most at least know something about them, so this is a great question to find out about what kind of guy they are – Showy? Adventurous? Practical? He’ll probably ask the question right back at you, so have a think beforehand.

3. “Have you ever had a run in with the police?”

Guys appreciate a girl who can ask a lighthearted question and they often give rise to the retelling of a hilarious story. Plus you get to find out if he’s willing to admit to any serious crimes; it’s probably best to find this out in the early days anyway!

4. “What are the 3 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 3 worst characteristics which is bound to bring out some entertaining answers.

5. “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.

6. “Shall we split the bill?”

Amazingly, this can be a bit of a contentious subject, but most guys really appreciate you at least offering to pay your way on a date. Be aware that if you offer, they have every right to take you up on it and you certainly shouldn’t hold this against them. We are modern women online dating after all!

7. “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:

1. “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.

2. “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.

3. “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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