Five revealing questions to ask on a date

·4-min read
Senior couple tourists at the city
Senior couple tourists at the city

The internet has plenty of advice to offer when it comes to what NOT to say on a date - but what should you ask? While we can't promise that these questions will result in success, they should help you get through any awkward pauses.


See also: Dating in your 50s-plus? What NOT to ask on a first date

See also: Dating after divorce - dos and don'ts

Firstly, some words of advice
While it can help to have a few 'ice breaker' questions in mind, don't get too hung-up on them. Your aim is to start a conversation. Ask question after question and it can start to feel like an interrogation – so use them sparingly!

There's another reason not to go with a list of questions and doggedly work your way through them. If you're constantly thinking about what to ask next, you're not going to be listening to your date's responses – and hopefully they'll say something you can add to, or they'll ask a question of their own.

With that in mind, here are five questions you might want to ask...

1. "If you won a travel competition to go anywhere in the world, where would you go?"
Asking 'feel good' questions can help to raise the mood – and who doesn't enjoy day dreaming once in a while? Your date's answer can reveal what kind of holidays they enjoy and how adventurous they are.

Does the idea of white-water rafting appeal, do they appreciate culture, or would they rather stay in a luxurious spa? Their answer can reveal much about their values – and also signal if you're likely to be a good match.

Asking a hypothetical question also helps to avoid the past. If you ask about their favourite travel destination, they may start talking about a holiday they spent with their ex – something you don't want to talk about on a first date!

2. "What's your idea of the perfect Sunday?"
This reveals what life with them may be like. Maybe they'd have a quick game of tennis, followed by a roast dinner in the local pub, and then an evening watching TV. Or perhaps they'd rather go shopping in Ikea? Whatever the answer, it can give you a clue as to whether their interests match yours.

3. "Does your family live around here too?"
If your date finds it hard to talk about themselves, asking about their family can help to take the pressure off. How much information they reveal – or don't – about the people closest to them can also give you some indication as to whether they have good relationships in their life, or things are complicated for them.

4. "When did you first get into...?"
Perhaps you know from reading your date's profile that they enjoy painting, yoga, or writing novels. Asking about someone's passion can be one of the best ways to get them talking – as the focus is on the thing they enjoy, rather than themselves.

Ask when your date first got into their hobby, how long they've been doing it for, and what they enjoy most about it. You may have no interest in stamp collecting or wine tasting or whatever it is - but how someone talks about their passion reveals a lot about them. What kind of terms do they use to describe their interest - are they ambitious, competitive, spiritual? The things we do for pleasure (rather than commitments of work and family) can reveal much about a person - so listen carefully!

5. "Is there something you'd like to try - but never have?"
Depending on the answer, this can help you set up a second date. Perhaps they've also wanted to have a go at ice-skating, or scuba diving? You might also ask "Is there a skill you wish you had?" This could lead on to arranging a singing workshop, cookery course, or horse riding lesson. This kind of question not only has the potential for fun, it can also be surprisingly revealing - tapping into their past and hopes for the future.