

10 questions you should ask on your first date
Navigate your first date in style with these top tips
Words: Gentleman's Journal
A first date is tricky territory. You want to get to know them, but you don’t want the dinner or drinks to come off as an interview. So we’ve rounded up 10 of the best questions to ask on a first date, if you'd ideally like a second.
What would you do for work if you could do anything?
Asking about someone’s dream career is a great follow up to asking what their current job is. They might feel somewhat indifferent about their current work situation, but their dream job will give you an insight into their values, ambition and drive.
Have you read anything interesting lately?
This is a great question to open up a conversation about books, but also presents an opportunity to get stuck into whatever viral New Yorker long-read is doing the rounds.

What are you looking for at the moment?
People don’t like wasting their time, so as as much of a cliché as this question may seem, it’s a for a cliché for a reason. They'll appreciate you being upfront about your intentions, and it’ll ensure no future miscommunications.
What is your family like?
Asking about family is great way to make your date feel comfortable – and find a little out about their upbringing whilst you’re at it. You can talk about where they grew up, and hopefully find some common ground between the two of you.
Tell me about your friends
This is an important question, as the people that your date surrounds themselves with will tell you a lot about them.

What's your favourite trip you've been on?
Travel really does broaden the mind, and most people will open up hugely when talking about past trips they’ve enjoyed. Reminiscing about their best days will put them in a great mood, and it gives you an opportunity to talk about your own travels, too.
What's something I would never guess about you?
This question gives your date the opportunity to be as revealing as they like about themselves. Keep it flirty and lighthearted but also give them the space and time to get deep if they feel the need.
Where's your favourite place on earth?
This question allows you a glimpse into the sort of lifestyle your date leads. Their favourite place is in the sea, swimming with sharks? You can deduce that they're an adventurous type. Their favourite place is cosied up beneath their duvet? Probably not so adventurous.

What's something you'd love to learn or get better at?
Asking this question will help to reveal your date's aspirations and interests, as well as signal their capacity for self-awareness and self-growth.
What's the worst chat-up line you've ever heard?
Finally, an opportunity to have a giggle with each other, which is always essential on a first date.
For more dating advice, read our guide to buying a drink for a stranger...

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