10 phrases a shy person can use to help get a conversation flowing

“It’s not what you know, it’s who you know.” This saying used to make me die a bit inside, but not because it isn’t true. 

In fact, there’s a lot of truth in it, which is why knowing how to network (another word that makes me feel a bit of dread) is such a valuable skill, especially career-wise. 

I’m not a fan of it, mainly because I’m a shy person. Who has to do a lot of socialization for work and personal life. Talk about a disastrous combination! 

Fortunately, I’ve learned a few tricks that have helped me go past my feelings of dread and nudge a conversation along. One of them is knowing the right phrases to use. 

In this article, I’ll share them with you. Hopefully, they’ll work as well for you as they do for me!

1) “I love your [item], where did you get it?”

I’ll start with  my personal favorite. In fact, I used this one very recently at a book festival I had to attend. And of course, it worked like a charm, like it always does. 

You see, it starts things off on a positive note. People can’t help but be disarmed by a compliment, and that’s your easy way in.

Not only do you lift their spirits up right off the bat, but this question can often steer the conversation in an interesting direction. 

For example, at the book festival, I told a lady, “I love your earrings! Where did you get them?” 

Turns out they were a gift from her sister, who had an artisan jewelry store. That led to a discussion of artisan jewelry, then artisan bags, which then turned into a conversation about sustainability. 

I mean, you just never know where a conversation can take you

And take note, it doesn’t have to be just items. You can also compliment them on the intangibles, like their sense of humor or their extensive vocabulary. That’s likely going to lead to an interesting conversation as well.

2) “What’s your take on [recent event]?”

Looking for a way to connect without getting too personal? Try asking about their opinion on a certain event. 

One thing to remember, though, is that certain topics – especially politics, religion, or civil rights – might be too hot to handle. They can be divisive or uncomfortable for the other person to discuss. 

The good news is, this is a versatile phrase. It doesn’t have to be anything heavy if you don’t want it to be. It can be about general and lightweight stuff like: 

  • A new TV show or movie 
  • A recent celebrity scandal
  • The latest scientific breakthrough
  • A surprising historical fact
  • A new food trend

The goal here is to spark their interest and stimulate a conversation that’s mutually engaging.

And to make it less awkward, sometimes I do a little trick – I scroll through my phone, look up, then ask the question, as if I’d just read about it and would now like to discuss it. 

Somehow that makes me seem more natural, as if I hadn’t just spent a few anxious minutes racking my brain for something to say! 

3) “I’ve always wanted to know more about [insert profession/ hobby]. Could you tell me more?”

Asking someone about their job or hobby is another wonderful way to get them talking because these are areas they’d be typically comfortable and knowledgeable about.

Besides, isn’t it interesting to know what people do with their days? No matter how shy you are, that’s got to be something you’re curious about. 

And the beauty of this is, you can follow it up with this next question…

4) “How did you get into [their profession/hobby]?”

I find that this really gets conversation flowing and solidifies connection even more. Because it shows you aren’t just being polite – you’re actually interested and inviting them to delve more into the topic. 

There’s something deeply human about sharing our journeys, and this question taps into that instinct. Think about it – even if you’re shy, don’t you love talking about your own interests? 

Sure, you might feel comfortable sharing only with people you’re close to, but the fact remains that talking about yourself makes you feel seen and heard. 

The same goes for anyone else you talk to! 

5) “What’s it like?”

Did someone mention a recent trip to Mexico? Ask them what it was like. 

Has someone started a new job? Ask them what it’s like. 

Does someone deal with difficult people on the daily? Ask them what it’s like. 

See how it works? “What’s it like?” is an all-around ice-breaker

In my experience, this phrase works wonders because it invites sharing, whether it’s life experiences or advice.  It gives the other person an opening to offer their insights and makes them feel important.

6) “What’s the highlight of your week so far?”

Perfect for the water cooler. Or wherever you and your co-workers take a break. 

For me, this is a hundred times better than the clichéd “How are you,” which is, frankly, a dead-end question because all it often elicits is the usual, “I’m good, thanks.”

This one’s more engaging, as it asks the other person to share something specific. 

From there, you can jump off of whatever they say, whether it’s an exciting new project or the announcement of a bonus. 

And you know what? This one’s got an underlying vibe of “We’re all in this together.” As in, we’ve all got ups and downs, and here we are sharing what makes us feel good right now. 

If that doesn’t build a connection, I don’t know what will! 

7) “I can relate/I hear you”

Speaking of connection, you can’t go wrong with this one. It’s an automatic connector. 

What this carries is an empathetic and understanding tone. You’re telling the other person, hey, we might not know everything about each other, but we’ve got this one thing in common. Isn’t that fantastic? 

For instance: 

A: “Work has been a real beast lately. I’m swamped with tasks up to my eyeballs!”

B: “Oh, I can relate. I’ve been doing overtime this whole week myself. How are you holding up?”

By connecting your experience with theirs…voila! Instant rapport and conversational flow!

8) “Have you had any unexpected challenges with [relevant topic]?”

What about struggles? Does that get people going? You bet. 

Why does this work? Well, because people love talking about their struggles and how they overcame them. It’s that simple. 

And for me, a shy person who’s also deeply curious about the experiences of other people, it’s really satisfying. I feel like we’ve gone past the basic pleasantries and begun delving deeper into things that truly matter. 

I love asking this of the people I meet at parties. To date, I’ve learned about so many things from this question alone, such as: 

  • How difficult it is to get a bill passed in government
  • The emotional stress and burnout of healthcare workers
  • How salespeople deal with rejection
  • The unique solutions people come up with for budget-friendly weddings
  • How professors deal with plagiarism and entitled students 

As you can see, that’s a pretty diverse range of knowledge that goes way beyond small talk!  

9) “That’s interesting. Tell me more…”

Or its more hyped up version: “Wait, what??”

I know that last one might be a stretch if you’re a shy and reserved person. But hey, I’ve used it myself, and so can you! 

The thing is, these phrases really go a long way in making people feel comfortable. And that includes you. 

Because what you’re doing here is making the other person the star of the conversation. You’re putting the spotlight on them, just like the other phrases here. 

So, you’re really satisfying two requirements here: 1) you’re learning new things, and 2) you’re making the other person feel special – thus building a connection. 

And that’s what effective networking is all about! 

10) “Oh, really?”

Yes, really. 

I can’t end this list without giving you this tried and tested phrase. It’s similar to “Wait, what??”, but more toned down, which might suit you better as a shy person.

“Oh, really?” serves as an interest-signifier, a story-prompter. You’re basically telling the person speaking that you’re truly invested in what they’re saying, and you’d like them to share more. 

And for some reason, it always works. Never have I encountered someone who simply replied with “Yes, really,” and left it at that. They always go on to share more.

Now, a word of caution – make sure to use this phrase sparingly. Too much of it will feel insincere and might even make the other person feel mocked. Or make you sound like a trained parrot. 

Final thoughts

Who says a shy person can’t keep up a conversation? With these phrases, you certainly can. 

But if you still need an extra boost, remember this – there’s nothing more effective in conquering shyness and getting a conversation flowing than genuine interest. 

Once you’re fully invested in what the other person’s saying, it will be harder for you to notice how nervous or self-conscious you feel. You’re less preoccupied with the impression you’re making because you’re too busy paying attention. 

Simply put, it’s all about shifting your focus! 

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Tina Fey

I'm Tina Fey, the founder of the blog Love Connection. I've extremely passionate about sharing relationship advice. I've studied psychology and have my Masters in marital, family, and relationship counseling. I hope with all my heart to help you improve your relationships, and I hope that even if one thing I write helps you, it means more to me than just about anything else in the world. Check out my blog Love Connection, and if you want to get in touch with me, hit me up on Twitter

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