From uncovering what really makes them tick to evaluating whether you’re a good match, take your date to the next level with these conversation starters

Sweaty palms, butterflies in your stomach, and a racing heart – first dates can be anxiety-inducing. The date might be a moment you’ve both been building up to for a while, or it could be the first time you’re meeting in person – either way, you want to make a good impression. All this comes together to create the perfect storm of jitters and second-guessing.

The frustrating thing is that often a first date feels high stakes. Will this lead to a second date? Perhaps something more? This pressure can make you clam up and forget who you are, what you're interested in, and why you came on the date in the first place. Cue: awkward silence.

But one thing that can make all those nervous feelings go away is easy, enjoyable, natural conversation.

UKCP accredited therapist, Tina Chummun explains that it's normal to be a little apprehensive: "First dates rattle even sturdy nerves, because they mix high hopes with uncertainty. You’re being seen in your most vulnerable way and sizing someone up at the same time. Remind yourself there are no ‘right’ questions or ‘perfect’ answers, just two humans finding a rhythm to see if they can create music together."

Dates are all about getting to know each other – finding out about the person they are, uncovering their passions and their values, and deciding whether or not you would make the perfect pair. You want to leave them with a good impression of you, and you want to be impressed by them, too. So, when you stumble across topics that lead to a deeper connection, it’s the key to uncovering where this date could take you next.

"Having a few questions up your sleeve will help to lower the pressure to ‘perform’," explains Tina. "It signals genuine curiosity, shows you care about the date, and helps you notice where your values, humour, and pace line up."

To help you on your journey to finding true love, we’ve put together 30 first-date questions, guaranteed to help you learn more about the person in front of you.

30 questions to ask on a first date

Before we get to the questions, here are a few tips on how to use them:

  • Memorise a few of the ones that feel most relevant to you and that you think will lead to the most interesting conversations

  • Rephrase questions to match your natural way of speaking, otherwise it could come across as too rehearsed

  • Use them for awkward silences. These are the prime moments to swoop in with a question to keep the chat flowing

  • Remember that conversation is a two-way street – be prepared to answer questions as well as ask them!

Personal values

Getting to know the foundational values that another person lives by can shine a light on any shared perspectives. Even if you come from different backgrounds, it's likely that you will be able to bond over similar experiences.

  • What's something important I should know about you?
  • What would you say your core values are?
  • Who do you admire?
  • What are you passionate about?
  • What's the best lesson you've ever been taught?

Relationship style

So you've got plenty in common, but what about how you both show up in relationships? These questions allow you to gently tease out what they are looking for in a partner and gives them the opportunity to do the same. Be wary of bringing up past relationships as this may feel a little too vulnerable for you both, so always tread carefully and keep things light.

  • What made you decide to begin dating?
  • What do you look for in a partner?
  • Do you believe that opposites attract?
  • What's your relationship with your family like?
  • What are your 'green flags' in a relationship?
  • What are your 'red flags'?
  • What do you think makes a successful partnership?
  • Would you describe yourself as romantic?
  • What makes you a good partner?

Life history

Our upbringing has a profoud impact on how we navigate relationships, dictates our attachment styles, and can inform our beliefs. Getting to know about their early life offers a chance dig deeper.

  • What were you like as a child?
  • Have you achieved any dreams?
  • Have you had a pivotal moment in your life, where you changed course?
  • Do you think you have changed much in the past five years?
  • If you could change one thing about your life, what would it be?

Aspirations

Looking ahead is a chance to feel out if you are both looking for the same things in life. Work and purpose is a good place to land because most people spend a lot of time and energy on their career, which makes it ripe for conversation!

  • Would you describe yourself as career-focused?
  • What's on your bucket list?
  • What are you working on right now?
  • What's the most interesting thing you've learned recently?

Personality

Asking them to reflect on their personality style can be a fun way to learn about their self-perception. What music to they like? Where to they spend their time? All of these little facts are gateways into deeper conversations and stronger connections.

  • Where do you find happiness in your life?
  • What would you say is your best quality?
  • How do you handle confrontation?
  • How important are friendships in your life?
  • What makes you laugh?
  • What song captures your personality?
  • What place do you love to visit time and again?
Once the conversation gets going, keep it flowing with these tips:

Ask follow-up questions. For example, if the question is, ‘Who do you admire?’, you can ask precisely what it is they admire about them, whether they feel influenced by them, and how they emulate this in their own life.

Engage in active listening. If you’re feeling nervous, it can sometimes be difficult to focus on what someone is saying, as your mind is already trying to grapple for the next thing to say. But try to stay present, and really listen to them speak. Feedback with non-verbal cues, such as nodding or humming, and ask clarifying questions that summarise what they’re saying, such as: ‘So you say you admire your brother because of his resilience, do you feel that attitude rubs off on you, too?’

Find their passion points. You can, of course, ask directly what they’re passionate about, but there are also more subtle ways of telling when someone is talking about something they really care about. Take a look at their body language – are they gesturing a lot, looking focused, and speaking in a louder voice? This is the perfect time to go off-script and pursue a line of conversation that’s naturally creating sparks. You may even find yourself nodding along and uncovering a new passion of your own!