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How To Save A Failing Conversation With 4 Questions

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Awkward first date? Standing around with an acquaintance while you wait for your mutual friend to come out of the bathroom? Partnered to work on a project with someone whom you share nothing in common? We've all been there.

When you can't just walk away from the other person, lulls and pauses in the conversation are bound to happen. You wrack your brain for something to talk about but it feels like you've exhausted every possible topic.

You can't just blurt out a bunch of random questions because it will feel forced and could make the other person uncomfortable.

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Instead of panicking and having a pointless talk about the weather, here are four questions that you can naturally throw into the conversation when you feel it struggling.

1. "I like your ______. What's the story behind that?"

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This question is the easiest one, unless the person is wearing the most generic outfit you could think of. Simply pick something interesting and unique on the person.

The older and more vintage something looks, the more likely it has a story behind it. This also works really well with tattoos. Complimenting them on something simple like jeans isn't going to get you anywhere. If anything it will seem more forced.

Use details from the other person's story as a jumping-off point for your own stories such as the history behind interesting objects you own.

Is their shirt from a thrift store downtown? Talk about your favorite bar on that street.

Is their tattoo a drunken memory from spring break in college? Bring it back to a crazy college story of yours.

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2. "What made you fall in love with your job/college major/hobby?"

People love talking about things they're passionate about. It's even better when you dive deep into the reasons why someone is passionate about something.

This question is a better substitute for common questions like, “What do you enjoy about being a [person's job]?”

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Sharing a story makes for a better conversation than just sharing a finite list of reasons why you like something.

3. Share a personal problem or experience then ask, "What do you think about that?"

People like feeling useful. We can't help it.

So, when you present the other person with a problem that only someone with their expertise can answer, they'll feel special and become more invested in the conversation.

For example, if your date likes cars, talk about how your current car is all beat up and you're looking for recommendations on which car to buy next.

If you know the other person loves to garden, ask for advice on how not to kill your indoor plants.

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The one rule here is to not make it weird.

If the other person is a doctor, don't talk about the weird mole on your lower back. Also, even if the other person is a psychiatrist, don't unload your personal traumas.

This is especially true if it's your first time out with this person. Stick to topics that speak to the other person's interests.

4. Make an observation about your surroundings.

When people don't know what to talk about, they oftentimes mention the weather and then have a thrilling thirty-second conversation about what the weather was like yesterday and what the weather will be like tomorrow.

You probably shouldn't talk about the weather to begin with.

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However, by following the right steps, you can turn a weather observation into an actual conversation. Instead of rambling about the weekday forecast, what you should be doing is using the current weather as a jumping-off point to talk about something else.

For example, maybe it's raining outside. Use this to talk about how you like to stay in bed and watch your favorite movie when it rains. Then ask, “What's your favorite movie when it rains?”

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This can lead to an entire discussion on movies, which can transition to any topic even slightly related to said movies.

Another option is an observation about someone on the other side of the room.

Use this to tell a funny story from your second year of college when you did something ridiculous. Then ask, “Did you ever do anything stupid like that?” Then you can have an entire conversation telling each other stories about funny and embarrassing things you've done.

Although this question has several steps, it's a foolproof way to get the conversation flowing as long as you end with a question for the other person.

If you don't give a prompt, the other person is more likely to just say “that's cool” or “that's funny,” and then you're back to silence.

If all else fails, text your roommate asking them to call with a fake emergency. "I have to go, my apartment is flooding" works every time.