Starting a conversation with someone you fancy can feel intimidating, no matter how old you are, but it really doesn’t have to be.
The trick is to keep it casual, fun, and natural — without overthinking every word. Whether you’re trying to chat up someone in person or sliding into their DMs, there are plenty of ways to break the ice without making it awkward. Here’s how to strike up a convo in a way that’s laid-back and shows off your true personality.
1. Ask for their opinion on something casual.
People love giving their opinions, especially on things that don’t require deep thought. Asking something light like, “What’s your take on pineapple on pizza?” or “Would you rather have a pet dragon or a pet unicorn?” is an easy way to get a conversation going. It takes the pressure off both of you and makes it feel like a fun chat rather than an obvious attempt to flirt. Plus, playful debates over random topics can lead to some great banter, which is always a win.
2. Use a compliment that isn’t about their looks.
Compliments are great, but when they’re too focused on appearance, they can feel a bit generic. Instead, go for something more personal, like “You’ve got such a great laugh” or “I love your music taste — your playlist choices are elite.” It shows that you’ve noticed something unique about them, which makes your words feel more genuine. Plus, it naturally opens the door for them to respond and keep the conversation going.
3. Make a comment about your surroundings.
If you’re in the same place, whether it’s a party, a coffee shop, or even a bus stop, use it as an easy way to start talking. Something like, “Is it just me, or is the music in here way too loud?” or “I think we might have the slowest barista in the country” can break the ice. It’s a simple way to get chatting without feeling forced. The more relatable the comment, the easier it is for them to jump in and respond naturally.
4. Ask them for a recommendation.
People love sharing their favourites, so asking for a recommendation is a great way to get them talking. Try, “I need a new series to binge — what’s the last thing you watched and actually loved?” or “I’m on the hunt for a decent coffee spot — any suggestions?” It’s an effortless way to start a conversation that feels natural, and it gives them the chance to talk about something they enjoy. Plus, if they’re into the same things as you, you’ve already got something in common.
5. Be playful with a fun ‘what if’ question.
Hypothetical questions make conversations way more interesting. Try something like, “If you could time travel to any decade, where would you go?” or “Would you rather fight one horse-sized duck or a hundred duck-sized horses?” It keeps things light-hearted and fun, which is way better than awkward small talk. Plus, their answer can tell you a lot about their personality, which makes the chat even more enjoyable.
6. Bond over something you both have in common.
If you already know a little bit about them, use it as a way to connect. Maybe you’ve got mutual friends, work in similar industries, or both love the same band — whatever it is, bring it up casually and use it to spark conversation. Something like, “I heard you’re into hiking — what’s your favourite place you’ve been to?” or “You support Arsenal? Brave choice!” works because it gives them something to latch onto. Finding common ground makes everything flow more easily.
7. Bring up a recent event or trending topic.
Current events, whether it’s a major sports final, a viral meme, or the latest Netflix show, can be great conversation starters. Try something like, “Did you see that wild plot twist in [popular show]?” or “Please tell me you’ve seen that ridiculous TikTok about…” It instantly gives you both something to talk about, and if they haven’t seen it, you’ve got a reason to send it to them later. Smooth.
8. Playfully challenge them to something.
A little bit of friendly competition can add some excitement to the chat. Try something like, “I bet I can guess your go-to coffee order — give me three tries” or “Quick — what’s your best useless fact? Let’s see who has the most ridiculous one.” It instantly adds energy to the conversation and makes it more than just polite chatting. The best part? A fun challenge can lead to inside jokes, which helps build a connection.
9. Reference something funny they’ve posted or said.
Source: Unsplash If they’ve posted something hilarious on social media or cracked a joke in a group setting, bring it up. Saying, “I’m still laughing at that meme you posted yesterday” or “That joke you made earlier was solid — I rate it” lets them know you’re paying attention. People love knowing their sense of humour is appreciated, and it’s an easy way to steer the chat in a fun direction.
10. Tease them in a playful way.
Source: Unsplash A little bit of playful teasing can create great chemistry if done right. If they spill their drink, you can joke, “Smooth move — you do this often?” or if they make a bold food choice, you could say, “Controversial pick — I need to know your reasoning.” The key is to keep it friendly and fun, never mean-spirited. A bit of back-and-forth banter makes the conversation feel effortless and flirty without trying too hard.
11. Pretend to ‘interview’ them.
Source: Unsplash If the chat is dragging, turn it into a fun Q&A. Try, “Alright, serious question — if you could only eat one meal for the rest of your life, what’s your pick?” or “I’m conducting a very important survey — what’s your unpopular opinion on pizza toppings?” It keeps the energy up and gives you both something fun to chat about. People love answering quirky questions, and it makes you stand out from the usual small talk.
12. Use an unusual but interesting fact.
Source: Unsplash Dropping a random fact can be an unexpected but effective way to kick off a chat. Something like, “Did you know there are more fake flamingos in the world than real ones?” or “Apparently, bananas are actually berries, but strawberries aren’t” makes people curious. It’s a great way to get them engaged straight away. Even if they call you out for your weird knowledge, it gives you something to laugh about.
13. Find an excuse to work together on something.
Source: Unsplash Whether you’re at a party, in a class, or at work, finding a way to do something together can naturally lead to conversation. Something simple like, “Want to team up for the pub quiz?” or “Can you help me decide between these two drinks?” works wonders. It takes the pressure off starting a conversation out of nowhere and makes it feel like you’re just naturally interacting. Before you know it, you’ll be chatting without even thinking about it.
14. Joke about the awkwardness of starting a conversation.
Source: Unsplash If you’re nervous, why not just own it? Saying something like, “So, I’ve been trying to think of a cool way to start this conversation, but here we are…” makes the moment feel relaxed and fun. It’s honest, relatable, and takes the pressure off both of you. Sometimes, acknowledging the awkwardness makes it disappear completely.
15. Just say hi and see where it goes.
Source: Unsplash At the end of the day, the simplest approach is sometimes the best. A confident “Hey, how’s it going?” is often all you need. If they’re interested, they’ll take it from there. Overthinking can kill a conversation before it even starts. The key is to relax, be yourself, and enjoy the chat rather than stressing over the ‘perfect’ opening line.
