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Awkward Date? Conversation Tips from a Trained Journalist

by Mattie Johnson | Sep 17, 2026 | Student Guides | 0 comments

Conversation is like playing a game of catch. Players must take turns throwing the ball, catching the ball and throwing it back.

All too often I hear about, and have experienced, dates where conversation seems stilted. There's this stale feeling that kind of lingers in the air. And one, or both, of you might be thinking "just one more hour." And I wonder if this can come from a silly, unspoken fear that dates are meant to be more flirty than friendly.

Since becoming a reporter, I've learned that some of my interview skills can also help stagnant conversations, even with people who may initially struggle to play conversational catch. However, its also important to keep in mind that dates aren't interviews or interrogations. As far as you should be concerned, a first date is you simply getting to know a new friend. So, don't put too much pressure where there shouldn't be any! Just chat as friends!

Everyone has a stories, interests, opinions and quirks, and finding what makes them light up can be really fun! Here are some tricks I use in interviews and have also implemented when conversations seem to drift.

Be Curious - Don't be afraid to ask a follow-up question.

Young couple sits at restaurant booth.
Young couple chats on date. Image credit: Scroll Media Library

Ask your date questions because you genuinely want to know more about them. Curiosity may be the most important skill on this list because with out it, conversation stops. If you ask a question and their answer makes think up another question, go ahead and dig a little deeper.

Reporter's Tip: I suggest avoiding dead end questions, (questions you would ask a Magic 8 Ball.) Asking open-ended questions that invite elaboration can help both people open up. If you do use a dead end question, I find using a variation of "tell me more about that" works like a charm.

What can this look like?

Person 1: How was your summer?

Person 2: It was good. I worked at a summer camp!

Person 1: That's so fun! What was that like?

Be Attentive - Notice which topics are energizing.

Listening to what your date is saying and paying attention to how they talk about different topics is a great conversation guide! Pay attention not just to what they say, but what they seem excited to tell you about. Focus more on what they are saying and less on what you want to say next. This can also help you channel more curiosity questions!

Reporter's Tip: If they light up when talking about something, dive into that. See what about that topic makes them so happy. And If you think something is cool, generous or smart verbalize that! Everyone likes to be recognized and complemented!

What can this look like?

Person 2: I worked at a summer camp!

Person 1: That's awesome! What made you want to work at a summer camp?

Be Generous - Give them something to respond to, too.

Young couple sit at restaurant on a date.
Young couple sit and chat at restaurant. Image credit: Scroll Media Library

Remember, this isn't an interview or an interrogation. It's a friendly game of catch! Sometimes "throwing the ball back" doesn't mean a consistent question-answer pattern. It can mean sharing a story, making a joke or offering your own thoughts. You don't need to ask a question and move to a new topic every time someone goes silent. Offering your own thoughts can help you and your date to feel more comfortable, and it gives them the opportunity to ask you curiosity questions.

Reporter’s Tip: If you can tell your date's thought has wrapped up, and you have a related story in your head, I would say go ahead and share it!

What can this look like?

Person 2: I love kids and I think helping them with activities is super rewarding.

Person 1: Yes! Kids are the best! I was in charge of the activity days kids back home, seeing them enjoy the activities I put together was so fun. One time I had them make...

Next time you're on an awkward date, just remember that right now, you are just friends getting to know each other. You could even throw some absurd questions out there for fun! I've had conversation, and light-hearted debate, break out amongst coworkers when I asked "If you were a raccoon, how many empty soda cans could you snatch and eat from the recycling bin?"

And keep in mind, these are skills, so anyone can develop them! If conversation is tricky for you in general, try using these skills with people in your classes, at church or even with your roommates. The more you use them, the more seamless it will be when it really counts!

If there is one thing you take away from this article, I hope its this: Good conversation comes more from being interested in others, rather than being interesting yourself.

  • Desk Editor

    Mattie covers Scroll's Art and Business beat and enjoys mentoring her practicum students and interacting with people in the community. She has always enjoyed the fine arts and hopes to share stories and insights that uplift and inspire her readers.

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