What three things matter most (and least) to you in your life right now?

Dr Sarah Davies, counselling psychologist and author of How To Leave A Narcissist For Good: “Getting to know what matters most and least can help you both to understand each other’s priorities and values. While we can have lots of differences (different backgrounds, hobbies, interests), most lasting successful relationships are down to people who share similar values. If what’s important to you right now is settling down and starting a family and you discover your date’s main focus is travelling, this could be an issue. Equally, what do you both care least about?”

What do you like to do outside of work?

Dr Becky Spelman, psychologist and founder of the Private Therapy Clinic: “This question will help you to understand your date’s interests and what brings them joy outside of their professional life. It opens the door for conversation about shared hobbies or potential activities you could enjoy together.”

What are you currently looking for in a partner?

Paul Brunson, global relationship insights expert at Tinder: “No one wants an awkward and stilted date, with interview-style interrogation but it’s important to get to know someone’s intentions. And it’s perfectly fine if they say that they don’t know, but it gives you a base to see if you’re on the same page.”

What’s difficult about relationships?

Charlotte Fox Weber, psychotherapist and author of What We Want: “It may sound cynical, but I think it’s deeply encouraging if people on a first date discuss the difficulties of relationships. There’s a lot that can be revealed in how someone approaches challenges, and discussing struggles and fears can open up hopeful possibilities.

“Whether people are experienced or sheltered, every human being has hopes and fears around relationships. I like the idea of starting as you mean to go on, and radical honesty, albeit in a small and safe dose, allows for comfort and confidence in showing vulnerability in a reasonable way and seeing how it lands.”

What made you interested in going out with me?

Jade Thomas, psychotherapist and founder of Luxe Psychology Practice: “This allows them to share with you what stood out to them about you, which can be very telling about what is important to them in a relationship or partner. The answer also might give you a good idea of their intentions for dating, if they haven’t been clear on this already.”

What is the most annoying thing about you?

Tasha Bailey, psychotherapist and author of Real Talk: “When we’re dating someone new, we put on the very best version of ourselves. But it can be both tiring and nerve-racking to hold ourselves to such high standards. This question can help to ease that expectation for yourself and your date. And it can be a great bonding session to discover if you have similarly annoying traits, as well as letting you know if your date has any habits that are non-negotiable for you.”

What is the one thing you want me to know about you?

Eimear Draper, dating coach and founder of Kindling Dating: “This is a really great one to get to see what someone is passionate about. It’s also good for bringing any deal breakers to the table quickly. For example, people with kids are often unsure about when to tell people they have kids, so this could be your window. Or if you practise a particular faith and it’s important to you that the other person accepts it, here’s your chance.”

Have you ever broken someone’s heart?

Limor Gottlieb, founder of Love Evolved and a doctoral relationship researcher at Brunel University London: “Some of the most important types of questions on dates are daring. Research shows that people tend to play it safe on dates by sticking to topics like hobbies or favourite foods. This comes from a fear of rejection, but the paradox is that the conversations tend to be dull and boring which can ultimately lead to rejection.

“So, instead of talking about their pets or favourite sports team, try to ask questions that allow your date to share something personal about them like if they have ever broken someone’s heart, how they lost their virginity or about their sexual fantasies. Research shows that people tend to be happier and more excited after these types of interactions than those who stick to superficial small talk.”

What are your plans for later in the year?

Psychotherapist and Counselling Directory member Rosalind Miles says: “Understanding each other’s goals and aspirations can also help you to understand if you are compatible, and if you want the same things in the near future. If you want to travel and seek adventure, but they want to sit on the sofa all weekend, then it may be a sign they are not the one for you.”

Who do you spend most of your time with?

Georgina Sturmer, counsellor: “This isn’t about grilling them on their upbringing or how many friends they have. It’s about getting a sense of who they value and who they rely on. And perhaps where a new partner might fit among their existing relationships with family and friends.

“Sometimes a simple and vague question can tell you more than something really specific. Notice whether they talk about work, friendships, family or hobbies. Maybe they’ll dodge the question entirely. And see whether they show equal curiosity about you, and your support network.”

How important is sex in a long-term relationship to you?

Dr Tara, sex and relationships expert: “Let’s be real. Sex is very important for some people and not so much for others. Often it becomes a big point of tension for couples in romantic relationships. I strongly believe it’s important to date people that have similar sexual attitudes to you to prevent resentment in the future.”

What is it that you do that makes it challenging to be in a relationship with you?

Dr Kalanit Ben-Ari, a couples and family therapist: “Another way to ask this is, ‘If I had an intimate conversation with your ex, what would they say makes it challenging to be in a relationship with you?’ Asking this can shed light on the person’s self-awareness, their behaviours and their understanding of the impact of these behaviours on their partner. It also demonstrates the ability to reflect and take responsibility for what isn’t working.”

Where do you see yourself in five years’ time?

Hendrix Hammond, psychotherapist and spokesperson for the UK Council for Psychotherapy (UKCP), says: “This question holds significant importance as it provides insight into whether your goals and achievements align with your potential partner, allowing you to evaluate compatibility. Many couples have regretfully confessed that neglecting to discuss their long-term aspirations in the early stages of a relationship led to conflicts when making crucial life choices. By initiating this conversation early in the dating journey, you gain the clarity needed to make informed decisions about investing in the relationship or considering alternative paths.”

13 experts reveal the most important questions to ask on a first date