Relationship experts share the questions to ask before a date
Photos: Getty
The world of dating is often hard enough without adding miscommunication and misunderstanding into the mix, which is a surefire recipe for heartbreak. Imagine having the answers to general questions such as ‘What are your values?’ ‘Where do we disagree?’ right at the start – think of all the time, tears and anxiety we might save our future selves!
Surely, it’s best to be as honest and upfront as you can, before you fall in deep, to protect yourself, and your prospective partner, later. But how do you go about asking what could be quite probing questions with someone you’re yet to really get to know? And what exactly do you ask? We challenged two relationship experts to put a little quiz together for potential boyfriends and girlfriends. This is what they said:
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Giovanna Smith is a professional matchmaker, relationship expert, and founder of Perfect Fusions – a bespoke matchmaking agency helping people find meaningful, lasting love. Drawing from her own journey through the highs and heartbreaks of love – including a difficult marriage and dating challenges – she brings wisdom, warmth, and a deep belief in second chances to everything she does. She says:
When you meet someone and the chemistry is there, it’s easy to get carried away – especially when we’ve been waiting for something (or someone) to feel exciting again. But if there’s one thing I’ve learned – both personally and professionally – it’s this: real love isn’t built on chemistry alone. It’s built on alignment. And knowing whether you’re truly aligned with someone starts with asking the right questions, early on.
As a matchmaker, I help people go deeper than surface attraction. These are the three key things I encourage my clients to explore before they take that next step into something more serious. These aren’t questions to fire off like a checklist – but gentle openings that can help you get to the heart of who someone really is.
1. What does a healthy relationship look like to you?
This question opens up so much. It shows you how someone views love, connection, and partnership. Do they believe in growing together, or keeping plenty of space? Do they value emotional closeness or practical support? There’s no “wrong” answer – but it’s important to know whether your ideas of love complement or clash. Listen closely – not just to what they say, but how they say it.
2. How do you handle conflict or tough conversations?
Every relationship will face tension. What truly matters is how someone responds when things feel hard. Do they shut down? Blame others? Or do they stay present, reflective, and open to growth? This question gives you an insight into their emotional maturity – and whether they’re someone who can weather life’s inevitable storms with you, not against you.
3. What are your hopes for the future, and do you see a partner being part of that?
This isn’t about demanding a five-year plan. It’s about tuning into whether your futures feel compatible. Whether someone dreams of a big family, wants to travel the world, or build a quiet, steady life – it’s helpful to know if your paths have the potential to walk side by side. Love needs vision. Without it, it’s easy to lose your way.
These conversations don’t have to be heavy or awkward. They can come up during a walk, over dinner, or when you’re sharing stories about past experiences. The goal isn’t to test someone – it’s to understand them. Ask with kindness, listen with curiosity, and trust what you learn.
Dating is more than finding someone who makes your heart race – it’s about choosing someone who brings peace to your now and future.
Counselling Directory member Alis Cox has an authentic, empathetic practice, working with people who may be experiencing anxiety, low mood, low self-esteem, burnout, depression, lack of confidence, overwhelm, people pleasing tendencies, trauma, stress, abuse and phobias. She says:
Relationships are hard, they take work, even the best ones. So getting to know who you're about to date helps you understand a bit more about what the future may hold. Of course, no one can predict the future, but these questions are a good starting point to help determine if this person is right for you to date.
1. What's your relationship with your family like?
The answer here is key – if they say 'We never argue' you know you're dealing with a family that pushes things under the rug. If they say 'Oh, we have a big bust up and clear the air' you know you're dealing with a family that understands how to air their stuff......and if they say 'They've all passed away' you know you're dealing with someone who understands grief and loneliness.
Any of these things just help you understand how the future may play out, and if you can work out how to create your own world together. Someone's family dynamics are super important, not just because you’ll be potentially joining them, but because it says a lot about how someone has evolved during their childhood and early formative years.
2. Do you like cats or dogs?
This really needs no explanation – how people answer this question reveals all you need to know! Also depending on how you feel about them you can see if you align. If they love cats and you hate them, it could be a deal breaker, or you know you've got to evolve into a feline lover. If they love dogs, you know there will be some dog loving walks ahead of you!
3. What's been the highlight of your life so far?
This is a great question to help understand someone, what makes them happy, what they feel success looks like and how they feel about the world in general. It can help you gain insight into what makes them tick, be it work, travel, family and friends – or all of the above. This question can really highlight how they feel about themselves and their world.
Gemma Logan is a relationship and wedding expert with 13 years' experience and a genuine love for helping people navigate love, connection and everything in between. She’s worked across the industry, from relationship advice columns to helping to plan weddings and hen parties and now shares insights and real talk on The Brighton Bucket List and beyond. She would ask:
1. What does a good day look like for you?
This one’s good because it tells you so much more than surface-level chit-chat. You’ll find out more than if they’re a morning person or night owl. You’ll get a glimpse into what genuinely brings them happiness.
Do they love quiet time with a book or do they come alive around people? If their perfect day is jam-packed with social events and yours is a Netflix and tea situation, it doesn’t mean you’re doomed but it does give you a real sense of how compatible your lifestyles might be. It also tells you how they handle downtime, stress and whether they find happiness in small things or need big moments to feel satisfied. It’s about values, not just hobbies.
2. Who do you feel most yourself around?
This question reveals a lot about someone’s emotional world. It tells you not only who they value but also how comfortable they are being vulnerable. If they say their best mate from school, their nan or even their dog, it gives you a lovely peek into the kinds of relationships they nurture. Do they thrive on deep connections or keep their guard up? Do they feel at ease being silly, serious, or somewhere in between?
The answer might also show how much emotional safety matters to them and what they might need from a partner in terms of trust and closeness
3. What role do you usually play in your friendships?
This one flies under the radar but it’s a total goldmine. Are they the organiser, the listener, the peacemaker, the joker, the advice-giver or the wildcard? How someone shows up for their mates often reflects how they’ll show up in a relationship.
If they’re always the go-to for support, they might be naturally nurturing but they could also be stretched thin. If they’re the flake or the comic relief, that tells its own story. It’s not about judgement; it’s about understanding their emotional habits and the dynamics they’re used to navigating.
4. If money, time and talent weren’t an issue, what job would you do tomorrow?
Here’s where you get a sense of their deeper dreams and whether they’ve still got a bit of wonder about the world. It taps into their imagination, their passions and whether they’ve got a playful or ambitious streak. Maybe they’d open a bookshop by the sea, become a jazz musician or train elephants in Thailand.
It doesn’t need to be realistic. The beauty lies in what it reveals about their heart and hopes. It can spark a brilliant, meandering conversation and show you where their head goes when anything’s possible. And that’s a powerful thing to know.
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