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Five questions you should ask on your first date, and five you definitely shouldn’t

Navigate your first date in style with these top tips

First dates can be a tricky business. You want to get to know her, but you don’t want the dinner or drinks to come off as an interview. So we’ve rounded up some top tips to help you on your way, and outlined five questions you should ask on your first date – and five you definitely shouldn’t.

Five questions you should ask on your first date, and five you definitely shouldn’t

What is your dream job?

Asking someone’s dream job is a great alternative to asking what her current job is. She might hate her current job, but her dream job will give you an insight into her values, ambition and drive.

What is the best thing you've read lately?

Something a little different, this question will similarly give you an insight into what drives her and her passions without seeming like an interrogation. Also, if she doesn’t read, it’s a good way to see that red flag early on.

What are you looking for in the dating world?

People don’t like wasting their time, so as cliched as this question may seem, it’s common for a reason. She’ll appreciate you being upfront about your intentions, and it’ll ensure no future miscommunications.

Five questions you should ask on your first date, and five you definitely shouldn’t

Do you have any siblings?

Asking about family is great way to make her feel comfortable – and find a little out about her upbringing whilst you’re at it. You can talk about where she grew up, and hopefully find some common ground between the two of you.

What’s the best place you've ever travelled?

Travel really does broaden the mind, and most people will open up hugely when talking about past trips they’ve enjoyed. Reminiscing about her best days will put her in a great mood, and it’s a great way to make you look interesting, too.

Five questions you should ask on your first date, and five you definitely shouldn’t

How long have you been single?

Do not ask this. It may seem like a good idea, akin to the ‘What are you looking for in the dating world’ approach, but the minute she starts looking back, your relationship will stop moving forward. And, for every five hilarious stories about break-ups she’ll have, there’ll be one ex who broke her heart and will never live up to you.

Who would be invited to your dream dinner party?

This may be another cliche, but we’ve got no idea why it persists. This isn’t dating-by-numbers, and you’re asking for trouble with such a mundane question. Either you won’t know the people she picks, she’ll say something overly serious or sentimental, or one of you will end up saying the other as a joke and it’ll backfire tremendously.

Five questions you should ask on your first date, and five you definitely shouldn’t

Do you want to go out again next week?

You should already know the answer to this. Read the situation, don’t ask the question. And, if you can’t figure out the answer, then the answer is no. She doesn’t want to go out with you again.

Who did you vote for?

Despite the fact that we seem to be having referendums and elections left, right and centre at the moment, bringing politics into a casual first date is a recipe for disaster. You’ll either end up arguing about each other’s political inclinations, or come off as incredibly boring. You want neither.

Shall we split the bill?

It’s the first date, gentlemen. You’re paying. Even if the date didn’t go well, she deserves to be treated like a lady. And, if you can’t deal with picking up the bill, you don’t deserve another date.

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