How to start a conversation without feeling awkward

If you've ever been at an event, standing awkwardly with a drink in your hand, pretending to text because you have no idea how to start a conversation, same.

I'm Ziyaan Virji. I speak on stages for a living and I run Leaders of Today, a platform that helps young people find opportunities, which means I end up at a lot of events. I still find it uncomfortable to walk up to someone and introduce myself.

I've also noticed I'm not the only one. Most people struggle with this, especially in my generation. One survey I came across put it at 67% of Gen Z who believe you don't have to meet in person to build a professional connection.

Which makes sense. We grew up in a digital-first world, social skills got rusty for a lot of us, and networking can feel more draining than exciting.

But here's the truth. The relationships that actually move your career, your business, or your mission forward are built in person.

So if you want to build anything that matters, you'll have to learn how to meet people, build relationships, and make your own opportunities. That starts with knowing how to open a conversation.

Why starting conversations feels so hard

Let's be real. Talking to people shouldn't be this hard.

Between social anxiety, overthinking, and the fear of rejection, most of us make it far more complicated than it needs to be.

The usual thoughts before approaching someone:

• What if they don't want to talk?
• What if I say something weird?
• What if I run out of things to say?

Here's what I realised. Most people at an event feel exactly the same way. They're also looking for someone to break the ice. They're also hoping to meet interesting people.

So if you take the initiative, you're already winning.

The three levels of conversation starters

Not every conversation starts the same way. Some situations call for quick, casual openers. Others need a deeper entry point.

Here's a three-level framework you can use at any event, networking situation, or social gathering.

Level 1: The easy openers

Low effort, low risk. Quick, simple, and effective. Use these when you have no idea where to start.

• Hey, I don't know many people here, mind if I join you?
• What brought you to this event?
• Have you been to an event like this before?
• I just heard someone mention [random topic]. What's your take on that?
• I love your [shirt, bag, shoes]. Where did you get it?
• What's been the highlight of your day so far?
• Who's the most interesting person you've met today?
• Do you think [speaker or topic] lived up to the hype?
• What's one thing you're hoping to get out of this event?
• I feel like everyone here is way more put together than me, do you feel that too?
• I know we just met, but do you think we could survive a zombie apocalypse together?
• What's the best thing you've eaten today?
• If you could only listen to one song for the rest of your life, what would it be?
• What's your go-to fun fact about yourself?
• Are you more of a walk-up-and-introduce-yourself person or a wait-for-someone-else-to-start person?

Level 2: The engaging hooks

Medium effort, builds momentum. Once the conversation is flowing, level it up with something more interesting.

• If you could invite one person, dead or alive, to this event, who would it be?
• What's a project or passion you're working on that excites you?
• What's the best piece of advice you've ever received?
• If you had to describe your job using only emojis, what would you use?
• What's a skill you wish more people had?
• If you could teleport anywhere right now, where would you go?
• What's a random fun fact that always blows your mind?
• What's the most unexpected path that led you to where you are today?
• If someone made a movie about your life, what would it be called?
• What's something you've always wanted to learn but never got around to?
• If you could swap lives with anyone for a day, who would it be and why?
• What's something that instantly makes you respect someone?
• What's a trend or habit you think we'll look back on in ten years and laugh about?
• If you could have dinner with your past self or your future self, which would you choose and why?
• What's a book, podcast, or article that recently changed your perspective?

Level 3: The deep dive

High effort, high impact. If the vibe is right and you're genuinely connecting, go past small talk.

• What's one belief you've changed your mind about in the past year?
• What's something you're incredibly passionate about but rarely get to talk about?
• If you could design your perfect life, what would it look like?
• What's a lesson life keeps teaching you over and over?
• What's the hardest decision you've ever had to make?
• What do you think people misunderstand about you?
• If money wasn't a factor, what would you be doing with your life?
• What's been your biggest win and your biggest challenge this year?
• If you could go back and give your younger self advice, what would it be?
• What's something that makes you feel truly alive?
• What do you think the world needs more of right now?
• Who's had the biggest impact on your life, and why?
• What's a random thought that's been on your mind lately?
• What legacy do you hope to leave behind?
• What's a defining moment in your life that shaped who you are today?

How to exit a conversation without it being awkward

Not every conversation will be a hit. Some will feel forced, and sometimes you just need to move on.

Here's how to leave gracefully:

• It was great chatting with you. I want to meet a few more people before the event ends, but let's stay in touch.
• I'm going to grab a drink, want to come with me? If they say no, you've exited.
• I just saw someone I need to say hi to, let's connect later.
• Hey, it's been awesome talking. Before I go, do you have a LinkedIn or Instagram?
• I have a feeling I'll regret it if I don't go introduce myself to [person]. Wish me luck.

The framework isn't the hard part. Walking over is. But the person you're nervous about approaching is usually standing there hoping someone approaches them.