
You’re on a date, you’ve made the effort, but the conversation is running a little on the side of, well, dull.
You’ve mentioned the same sort of things: family, friends, what holidays you’ve been on lately, or if you’re feeling brave: your past relationships. But it’s not the most titillating of exchanges. Is it them? Are they just unbothered by low-effort chit chat? Are they just happy discussing the proverbial weather?
We’ve all been there, a few Tinder dates here, a few Hinge dates there. The same sort of back and forth comes up, especially on first dates. So how do you make sure what you talk about is more interesting? How do you steer the dialogue away from being -God forbid- boring.
Well, look no further. Here are some date conversation starters which are very much not boring, and hopefully can be a little more open ended, keep the conversation flowing, and ease you into a less time wasting, more pleasurable, experience. It could also be quite elucidating as to how compatible you are and a good way to get to know one another more deeply.
- How do you show you care about someone? What is your love language?
- This is a great question as it not only tells you how someone shows they care, but also how they like to be cared for. Plus how caring they actually are. Understanding someone’s love language is a good way of building a solid foundation of trust and care, showing your love in a way the other person can truly feel it. When you know each other’s love languages it becomes easier to avoid complacency and do simple things to keep the magic alive.
- If you won the lottery tomorrow, what would you do with the money and would you tell anyone you won?
- A real eye opener to how someone works with money. Are they a saver, or a donator or would they splurge it all at once? Are you financially compatible? Sometimes couples don’t figure this out until living together, so it’s good to get an idea early on. Plus it’s fun to see what they’d do with a lottery win!
- The classic “Dinner party” scenario: name four people you would invite, dead or alive, to your ultimate dinner party and why? Bonus: would they get on?
- A way of understanding someone’s interests quickly: do they pick creative people, historical people, family members? It’s fascinating how much the people we’d chose to have dinner with, if anyone in the world, can tell us about ourselves and our own personalities.
- What would be your death row meal, and why?
- Again, a solid way of finding out someone’s favourite foods and meals: are they veggie or vegan, is that important to you? Are they secretly a sugar fiend or a lover of home cooked meals? It’s also pretty mouth watering to think of what you’d like.
- Is there something that you’re really proud of yourself for doing or achieving so far?
- Getting a little deeper now, what someone is most proud of can really open up the conversation on what’s important to them. What do they consider to be a great achievement, is it academic, or career orientated? Is it to do with family values or a selfless deed? Our achievements or what we consider pride worthy can say a lot about our values and how we view ourselves.
- If money was no object, list the top 5 countries you’d like to visit and where would you stay (caravan, villa, tent, cliff-side pod, 5-star hotel?).
- Ahh this is a really fun one. Of all the beautiful countries in the world, knowing where someone would love to visit says a lot about their worldview as well as interests in food, travel desires and experiences. Do yours align? Are we talking sun, beach and party destinations? Or more picturesque sweeping landscapes with nature at the core? Or perhaps a five star hotel kind of city lover? This can tell you a lot about what your future could look like for holidays!
- Can you tell me about a favourite memory you have as a child?
- Another deep one. Our childhood memories can hold a variety of emotions and nostalgia. Someone’s favourite memory can say plenty about someone’s upbringing. Does it involve a certain family member or pet? Is it a trip or playing with a toy? We can learn about their family dynamics this way too. It’s nice to see where the mind takes them.
- What type of music do you like to listen to and how does it make you feel?
- A slightly more generic question, but with the added layer of what emotions their favourite music brings out. Again, type of music can say a huge amount about someone and what emotions they actively desire to feel. Do they like the soothing nature of classical music? Or the rhythmic energy of house? Or is it more upbeat pop they can dance to and let their hair down singing?
- What are your biggest fears, if you have any?
- Not one for the faint hearted, and it may provoke a more surface level answer, like spiders. However if delved a little deeper, it can take knowing each other to a new level, and uncover deeper thoughts and feelings.
- Tell me something that you’ve been excited about lately.
- What do they enjoy? Getting to know what makes someone happy and excited can bring an uplifting turn to the conversation. Perhaps it’s a project or a hobby, or seeing a new family baby, or even going to a gig of an artist they’ve loved for years.
- Bonus question only if you feel comfortable: how often do you like to have sex in order to be satisfied?
- Much more of a flirty question, and obviously not one to just drop in randomly. If the moment arises, it can be really helpful to find out early on what someone’s expectations of an intimate relationship looks like. Do your answers align? Sometimes even with the most electric of initial chemistry, if sexual needs and wants ultimately don’t match, it can cause friction further down the line.
One thing to keep in mind would be to not treat the list as an interrogation or interview, use them sparingly when there’s a lull, often it sparks a longer conversation and can be eye opening as to personalities, interests and what make people tick.
Hopefully these conversation starters can help bring a little fun to the date, who knows it may even bring you closer!
Happy chatting!

