You’re fifteen minutes into your V-Day date with a new partner and you feel like you’re on your game tonight. Not a single awkward silence yet!

They’ve been doing most of the talking and you’ve been listening like a trooper. You can see they love talking so you’re letting them have the stage. Surely this is winning you points.

You throw in a few questions to keep the conversation going:

– “Wow, really… you went camping on the weekend?”

– “Where did you go?”

– “What did you do?”

– “Who did you go with?”

They tell you and you act like you’re interested. They’re answering your questions so they must be enjoying this. But wait a minute. Why does this conversation feel like you’re only scratching the surface? What have you really learned about your date?




The reason this conversation sucks is because you’re jumping from topic to topic like a frog jumps from lily pad to lily pad. There’s an entire pond of information about the other person right at your feet but you haven’t even dipped a toe in. You haven’t stuck to one subject for long enough to learn anything about the other person.

You might think you’re talking about one thing (camping) but in the space of 30 seconds you’ve changed the subject three times.

  • “Where did you go?” makes the conversation about a place.
  • “What did you do?” kills that subject and makes the conversation about an activity.
  • “Who did you go with?” kills that subject and makes the conversation about a group of people.

You’re collecting surface-level facts that tell you very little about who your new partner is. You’re asking empty questions.

You’ve probably only been seeing this person for a few weeks now so perhaps you’re not entirely comfortable with each other yet. That’s why you desperately want to keep the conversation going at all costs. But if you keep going the way you’re going, pretty soon you’ll run out of lily pads and the conversation will fizzle out. So will your connection with your new partner.

The pond will never run out of water though, so take a dive. Go deeper into each topic and find out what lies beneath.


If you want to build a strong connection you have to find out who your date is as a person. Learn what they like, how they think and what makes them happy.

If they tell you they went camping, find out what’s under the “camping” lily pad and learn about them as a person, rather than collecting facts.

You: Oh you like camping?

Them: Yeah, I love it.

You: What do you like about it?

Them: I love how quiet it is. Sometimes I just have to get away from the city.

You: Would you ever want to live away from the city? Somewhere quiet?


If they tell you they did some stargazing while they were camping, dive into that.

You: What do you think about when you look at the stars?

Them: I wonder whether we’re alone in the universe or not.

You: How do you feel about being alone?

Them: I guess it makes me feel like we’re so insignificant that nothing I do really matters.

You: Does that scare you or is it kind of motivating?


If they tell you they went with their family, find out about their relationship with their family.

You: Are you close with your family?

Them: I spend a lot of time with them but I don’t really share everything with them.

You: Because they’re monsters? (cheeky face)

Them: Nooo, haha. They’re really judgmental though. I just learned to hide things from them because I don’t want to be judged.

You: Do you think that’ll ever change?


Feel the difference? Now you’re actually learning about your new partner as a person. Instead of collecting surface-level facts you’re diving into the way they experience things. You’re building a connection.


Listening and hearing are two different things. Hearing is passive, while listening is active. In order to be a good listener you have to ask good questions.

Good questions help you understand the other person, while bad questions leave you with a collection of facts that you don’t really care about anyway.

If you can master the art of listening to understand, you’ll learn what your partner likes, how they think and what makes them happy. That’s the only way you’ll create a genuine connection with your valentine.

If you want to learn more about genuinely connecting with people through conversation check out the Meaningful Conversation Challenge, discover how to be an interesting date or learn more from our expert dating bloggers.