7 Brilliant Questions To Ask On A First Date

A first date is an opportunity to have a fun experience with a stranger. But it can also be exciting, nerve-wracking or a total disaster. Here are 7 brilliant questions to ask on a first date.

When you’re getting to know someone you have a crush on, it can be tricky knowing how to get the conversation started, and to how to keep it interesting and light-hearted so that you both enjoy the date experience.

On Chat2Date, you can have tons of practice chatting and flirting with friendly folk in a totally anonymous way. Should you happen to connect with someone who piques your interest, you can send flirty messages online or via SMS chat, and arrange to meet in person on a hot date.

These 7 brilliant questions are guaranteed to encourage great first date conversation, to identify compatibility, and to help you gauge more quickly if you have a connection that’s worth exploring more deeply.

  1. “How would your closest friend describe you?”

To get a feel for the role that your date plays in their closest friendship and social circles, ask them to tell you about how others would describe them. Their reply will give you an idea of their own perception of their personality.

The answer to this question also offers an invitation to explore their most important connections – like parents, siblings and BFFs. Paying attention to how they talk about other people will additionally give you an insight into their character.

  1. “What makes you unique?”

One of the easiest ways to connect with someone new is to get them talking about themselves. When they mention a hot topic, like their favourite movies, music, books or sports, you can easily establish a bond by sharing your own likes and dislikes.

You can also be cheeky and ask them to share a secret about themselves that they haven’t told anyone else. Or to tell you about a special talent or skill that they have.

  1. “What matters to you?”

Avoiding asking questions that are too specific – “what are your hobbies?” – or predictable – “where have you been on holiday?” – will make your conversation much more fun and interesting.

Asking a question about what they’re really invested in is a great way to discover what your date values and is passionate about, and if they share your ideals, principles and virtues. Besides learning what they value the most in the world, you’ll have an opportunity to experience a magical moment, when you catch a glimpse of light in their eyes as they share info about the people and things that are truly meaningful to them.

A date who values possessions over personal connections is likely to be a materialistic type, and therefore not your potential perfect partner, if you’re someone who cherishes relationships the most.

  1. “Where is your favourite place on the planet?”

To discover what kind of setting makes your date feel most comfortable and at ease, ask them to tell you about their ‘happy place’.

If they love to travel, their favourite place could be a vacation destination that inspires them to tell you stories about their adventures. If their happy place is somewhere closer to home, like a secret location where they go to unwind, relax and escape the world, you could learn about their life story and how they came to discover the special retreat.

  1. “Would you rather…”

While it’s great to ask your date some icebreaker questions that elicit deeper responses than superficial surface level chitchat replies, it’s also worth throwing in a few silly ones too…

You can have a lot of fun asking “Would you rather…?” questions about absolutely anything.

Start off by asking a few questions that are easy to answer…

“Would you rather go to the beach or the mountains?”

“Would you rather only drink coffee/tea or cocktails for the rest of your life?”

Next, get them thinking by asking some thought-provoking questions like…

“Would you rather be happy, wealthy, or healthy?”

“Would you rather find your true love or a suitcase filled with £1,000000?”

And just for laughs…

“Would you rather have skin that changes colour with your emotions or tattoos that appear all over your body whenever you tell a lie?”

“Would you rather have massive hands or gigantic feet?”

These random questions will highlight their sense of humour and potential compatibility.

  1. “What’s on your bucket list?”

Most people have a bucket list of things they would love to do and places they want to visit. Asking your date what’s on their list is an excellent way to find out what you have in common.

  1. “What was your first impression of me?”

Once you’re relaxed in each other’s company, you can ask a question that’s more personal.

The way in which your date describes you will help you get a sense of how much they’re into you. If the description is a good fit for your personality, or they’ve correctly gauged your sense of humour, interests and passions, you could be onto a good thing.

If their description is way off the mark, you can either share more about yourself, or cut loose. Someone who’s not paying you attention on a first date is unlikely to make much of an effort at any other time.

You can also give your date an opportunity to ask you any random question that they like, so that you can explore their emotional intelligence. If they don’t know what to ask you, it’s probably best to end the date and move on.