24 January 2025

Simple Tips to Start Conversations with Anyone

Megan

Let’s face it: striking up a conversation with a random person is terrifying for most people. You’re standing there, trying to figure out what to say, and all you can think of is that awkward silence creeping up like a slow-moving storm. But guess what? It doesn’t have to be that hard. You don’t need to memorize a set of pickup lines or read a bunch of self-help books on how to “win friends.” Starting a conversation can be easy if you just stop overthinking it.

So, here are some simple, no-nonsense tips to help you start conversations with anyone — whether you're at a party, networking event, or just standing next to someone at the bar.

1. Ask a Question That’s Not Boring

The easiest way to start a conversation is to ask a question, but don’t ask the same old boring crap everyone else asks. No one cares about “What do you do?” or “Where are you from?” Instead, hit them with something that’s unexpected and will actually get them talking.

Here are some good examples:

  • “What’s the best thing that’s happened to you this week?”

  • “If you could live anywhere in the world, where would it be?”

  • “I’m on a mission to try the weirdest food possible. What’s the strangest thing you’ve ever eaten?”

These types of questions make people think. And when people think, they talk. They want to share their experiences, and that opens the door for a real conversation, not just a boring exchange of pleasantries.

2. Compliment Something Specific

Compliments are a great way to start a conversation, but don’t just say, “You look nice.” That’s lazy, and it doesn’t lead anywhere. Be specific. Compliment something that stands out.

For example:

  • “I like your jacket. Where did you get it?”

  • “Your sneakers are dope. How long have you had them?”

  • “That’s an awesome tattoo. What’s the story behind it?”

Not only does this show you’re paying attention, but it also opens the floor for them to share a bit more about themselves. It’s like an instant icebreaker.

3. Talk About Your Surroundings (It’s Right There in Front of You)

If you’re really stuck for something to say, just talk about what’s happening around you. It’s the perfect way to break the ice, and it’s an easy segue into a deeper conversation.

For example:

  • “This music is awesome, right? What do you think of the playlist?”

  • “This place is packed! Have you been here before?”

  • “I can’t believe how crazy the weather’s been lately. Is it like this all the time around here?”

Talking about your environment is a no-brainer. You’re both experiencing it at the same time, so it’s an instant common ground. It doesn’t get more straightforward than that.

4. Use Humor to Your Advantage (But Don’t Force It)

Humor is one of the best ways to start a conversation, but don’t go trying to pull out some stand-up material you heard on Netflix last night. Keep it natural. A funny observation or a light-hearted comment can do wonders for breaking the ice.

For example:

  • “I’m pretty sure I just spent 10 minutes staring at that sign over there, trying to figure out if it’s a joke or not. I think I’ve been awake too long.”

  • “So, I walked into this place, and the first thing I thought was, ‘Okay, which drink is going to make me look the least awkward?’”

Keep it light. Don’t try to be the funniest person in the room. Just make a little joke to ease the tension, and chances are, the other person will play along.

5. Use the Power of Silence (And Not the Creepy Kind)

Sometimes the best way to start a conversation is to simply be there. People are often afraid of silence, but here’s the thing: silence doesn’t always need to be filled with words. Just existing in a moment and allowing the other person to start talking can actually create a conversation that feels natural and relaxed.

For example, if you're at a party, just stand next to someone, smile, and wait for them to say something. When they do, you’re already in the conversation. If you're sitting next to someone at an event, just make eye contact and say, “Hey, how’s it going?” Sometimes, allowing that little pause or bit of awkwardness is exactly what’s needed to get things going.

6. Be Interested, Not Interesting

One of the biggest mistakes people make when trying to start a conversation is focusing too much on themselves. They talk about their accomplishments, their life, and their latest trip like it’s some kind of audition. But no one wants to hear that. They want to feel interesting and valued.

Instead of talking about how cool you are, focus on making the other person feel cool. Ask them questions, listen to their answers, and really engage. People love talking about themselves. If you show genuine interest in them, you’re halfway there.

For example:

  • “That’s really cool. How did you get into that?”

  • “I don’t know much about that. Can you tell me more?”

  • “Wow, that sounds like a wild story. How did that happen?”

People can tell when you’re actually listening, and they’ll want to keep talking. All you need to do is ask the right questions and shut up long enough to hear their answers.

7. Don’t Be Afraid of Small Talk (But Don’t Make It Your Whole Conversation)

Look, small talk gets a bad rap. Sure, it’s not the most groundbreaking conversation, but it serves a purpose. Small talk leads to big talk. Start with something basic and watch the conversation grow.

For example:

  • “So, what do you do for fun around here?”

  • “Are you from around here, or just visiting?”

  • “I’m kind of new to this scene. Do you come to these things often?”

It might seem boring at first, but small talk is like opening the door. Once it’s open, you can start getting into more interesting topics.

Final Thoughts: Stop Overthinking It and Just Start Talking

Here’s the truth: starting a conversation isn’t some magic trick. You don’t need a secret formula or a special skill. All you need is to stop overthinking it and be open to connecting. Ask the right questions, be genuinely interested, and show some confidence. You don’t have to be perfect, but you do have to be real.

So, next time you’re standing next to someone at a party, on the bus, or in a waiting room, don’t panic. Just start talking. You’ve got this.