Five Conversation Starters that Create a Deeper Connection


So you’ve been chatting to your match online and now you are going out on a date. What then? Dating coach and writer Laura Yates knows how to make sure you’re not stuck on small talk

We’ve all been on those dates where it feels more like a job interview than simply having a nice time getting to know someone. Not much fun! To be honest though, when nerves get the better of us or we’re just a bit unsure what to say, it’s easy to go on autopilot and start reeling off a list of questions that don’t lend themselves to creating much connection. When you’re only talking about what you do, where you live, what music you like etc, but don’t go any deeper beyond that, it’s incredibly difficult to really get a sense of who someone is and what makes them tick. But don’t worry, it’s not about asking ‘deep and meaningful’ questions, which on a first date, you definitely want to steer clear of!

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Here are 5 conversation starters and questions that you can use on dates that take things away from the norm and allow the person to reveal more about themselves, their personality and what they’re about.

1) Where is the best place you’ve travelled to and why would you recommend it?

If a person has been somewhere that has been significant in their life or that they loved, they’ll very likely want to talk about it! It allows them to draw on memories of the place, share anecdotes and most importantly, talk about something they’re passionate about. This will help them loosen up and you’ll really get a glimpse of their personality beyond the nerves.

2) Who in history would you most like to have a drink/coffee with?

I love this one as it really gives you a sense about what someone is interested in, who inspires them and how they view life as a bigger picture. It’s usually very surprising and often funny who people choose, so can easily lead into other interesting conversation too!

3) What is it that you like most about your job?

The work/career question is inevitable as it’s how we spend most of our time. You can still go beyond the whole ‘what do you do?’ though. Asking what someone likes most about their job can actually reveal a lot! I used this one on a date recently and the answer he gave was that he loved working with contracts, meeting clients every day and seeing small businesses grow. This helped me understand that he pays attention to detail, is a people person and enjoys seeing others thrive. Those might not be huge things, but it gave me much more insight about him, than him simply telling me what he did for a living and then moving onto something else. It was also clear when he was telling me about it that he was passionate about his work and that itself can be an attractive quality.

Even if someone expresses that they don’t like their job, you can still ask them what they’d like to be doing instead (or their dream job) and why.

4) What would be your perfect day?

This is a great one as is fun, light hearted and really gives you a good idea of how your date would choose to spend their time in an ideal world. It can reveal what their aspirations and inspirations are and also, how creative and imaginative they can be when talking about something away from everyday real life.

5) What were you like as a kid? (You can even extend this to ‘I imagine that you were…….’)

Another one that draws upon memories and can be quite fun to talk about! It can also be surprising how different people were as a child to what they’re like now, and gives them opportunity to share stories about their childhood, family and school life. It’s a nice one to give you a more well-rounded view of who they are.

It’s helpful to remember that first date nerves are inevitable, so don’t think too much about the right thing to say or worrying about those ‘awkward silences’! Often when you just accept that those are going to happen, you can move through them much easier. So just relax, go armed with a few fun or interesting stories about yourself and remember that you can use your environment and where the date takes place as a source of conversation points too!

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Laura Yates is a relationship coach and writer who specialises in helping people through break-ups and heartbreak. Laura provides clients with bespoke tools, techniques and mindsets that enable them to deal with their emotional struggles whilst moving forward in their life with renewed energy and focus. Laura also helps people to build up their confidence, communication and interaction skills when getting back into dating.

 Find Laura on Twitter, Facebook, or on her website.

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