4 Nov 2014

How To Keep The Conversation Going on A Date

We’ve all been there. We’re 15 minutes into a date and that awkward silence hits. Your mind goes blank and it feels like light years have passed before either of you can figure out what to say next. You can’t for the life of you think of an interesting story to tell or the latest headline to discuss. What are you to do?

You ask a question instead. You don’t need to be interesting; you just need to be interested for your date to go well. When you are interested, the person is more intrigued than when you are interesting. Why? Because for a change, someone is interested in what they have to say, instead of being the self-centered person we’re all used to dating.

Next time you find yourself in that awkward silence, use some of these lines/questions to keep the conversation going on a date.


This line of questioning can encompass almost anything on the planet. Think of something they mentioned before and ask them to tell you more about it. Ask about themselves, their job, their dog, their family and so on.


People love the sound of their own voice. They love to tell stories. By asking how they got into their line of work, an organization, or even the online dating app you met on, you are inviting them to tell you a story.


When the purpose of the date is to get to know someone, an easy conversation starter is asking him or her about their goals, favorite things, hobbies, interests, and things they’re looking for?

Make sure that this doesn’t become an interview. The idea is to keep the conversation going so remember to reply with your own relevant stories and interests. Make sure to actually listen when the other person is speaking so that you can ask follow up questions.

Get more first date tips in my Never Have a Bad Date Again post.

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