First date questions to help you break the ice


Ywe don’t get a second chance to make a first impression, so when you go on a first date, you need a nice first date outfit, suitable venue and great first date questions. Even if you have previously laid the groundwork by chatting on a dating app or in a social setting, the date itself is the scenario that will determine whether a second meeting is on the cards.

Having a nice conversation is easy if you ask the right questions on the first date. There is evidence to show that people are perceived as more attractive when they ask dating questions, and even more so when they ask follow-up questions. In one speed dating study it was found that participants were more likely to pursue a second date if they were asked follow-up questions – ie. the date asked a question, listened to the answer, and then asked another question based on that answer.

With that in mind, here are some interesting and fun first date questions to inspire you.

1. How was your day?

You might be tempted to ask about their trip to the restaurant or if they’re enjoying the weather, but one of the best questions to ask on a first date is simply “how was your day?”. It’s an easy way to start a conversation that shows you’re interested in their well-being and what they’re doing.

If you end up talking about work, it’s a natural way for you to talk about your career. If they tell you about a recent movie or football game they watched or a big art exhibition they visited, it opens the conversation to talk about hobbies and interests.

Remember, if they’ve had a terrible day, then you have the opportunity to turn it around – ideally by ordering a few glasses of champagne…

2. What is a typical day at work like for you?

This is a better way to ask your date what they do for a living. It gives them the opportunity to delve into the specifics of their job rather than simply ditching their job title and moving on to something else.

This question can also yield some great work anecdotes. Within minutes, you might be sharing stories about your most obnoxious co-worker or bonding over hilarious experiences at a business meeting.

Suggested follow-up questions…

“What’s your dream job?”

“What are you most proud of in your career?”

“Have you thought about what you will do after you retire?”

“What do you do on the weekends?”

A classic first date question is “what are your hobbies?” but this can be surprisingly difficult to answer. More often than not, you’ll come across a cliché answer like “watching movies” or “playing tennis.” A better way to get a feel for someone’s interests (and how compatible they would be as a couple) is to ask them what they do on the weekends.

If your date brings up a favorite pastime, whether it’s going to the gym, walking a hill, baking, painting, or binge-watching old episodes of Star Trek, this is a great opportunity to find out more. Ask them how they became interested in the activity and, if you’re feeling brave, suggest that they introduce it to you sometime.

Suggested follow-up questions…

“What does your ideal Saturday look like?”

“Is there an activity you’d really like to try?”

“Do you enjoy lazy days or do you like to be busy?”

3. Do you have a vacation planned?

Traveling is one of the best things to talk about on a date, but it’s not always easy to initiate. You should not assume that your date has had the opportunity (or means) to visit many countries around the world. So asking about vacations is a great way to go.

Maybe your date is only on vacation in United kingdom, or they may have spent months backpacking abroad – regardless of their travel experience, a simple question about what trips they have planned is a great way to start this conversation.

Suggested follow-up questions…

“Which country did you like to visit the most?”

“If you could book a flight anywhere, where would you go?”

“What’s the worst tourist attraction you’ve ever visited?”

4. What is your go-to comfort food?

Food is another great first date question topic, and comfort food is a fun way to approach it. Whether you end up bonding over a love of spicy curries or start comparing notes on the best meal you’ve ever had, you’re sure to have something to talk about. It’s also a great way to propose a second date, whether you’re asking them to come and try your signature pasta dish or inviting them to your favorite restaurant.

Suggested follow-up questions…

“Who taught you to cook?”

“What is your most important piece of kitchen equipment?”

“Who is your favorite celebrity chef?”

5. What were you interested in as a child?

For almost anyone, talking about childhood is an easy topic to talk about. We all like to reminisce about those happy – albeit occasionally unpleasant – days and become nostalgic about our childhood hobbies, toys and friendships.

This question will get you both sharing some funny anecdotes about when you were kids. It’s also an easy way to get a feel for your date’s family life and personal history.

Suggested follow-up questions…

“Who was your biggest celebrity crush when you were a kid?”

“Did you have any pets?”

“What are your siblings like?”

6. What is your favorite TV show?

Nowadays, everyone has their favorite box set, a TV show that they enjoy on repeat or return to when they need a comfortable viewing.

Ideally, you’ll end up bonding over this question over your shared love of Friends, Downton Abbey or Game of Thrones – but even if your TV tastes are quite different, it’s still a great topic to talk about. After all, if your date hasn’t seen your favorite show yet (or vice versa), you can suggest a second date where you watch a few episodes with a good a bottle of wine.

Suggested follow-up questions…

“Which character from your favorite TV show are you most like?”

“Who is your favorite actor or actress?”

“Have you seen the trailer for this new show…?”

You may also want to ask your date about his preferences or find out if there is something he wants to get better at. You may find that you have common goals. You can use this opportunity to share your own ambitions – communicating these ambitions early on can help the relationship in the long run.

Remember, this is not an interrogation. Ask questions, listen to what your date has to say, and join the conversation by offering your experiences and insights. Don’t rush the conversation because you’re afraid of pauses – the odd lull is expected. Follow this advice and leave the rest to chemistry. Best of luck!

If you are single and interested in meeting like-minded people, join Telegraph dates. With over 220,000 like-minded single people, Telegraph Dating is the best place to find romance.

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