20 conversation starters that will almost always work when talking to strangers


You know how it is. You see someone you want to talk to, or that someone sees you, and the conversation begins. It’s easy to remember times when it doesn’t work out – maybe he used a bad pick-up line or you stumbled over your words when you tried to start chatting – but what about when you hit it off with someone for real? The conversation was interesting and funny, and made you want to get to know the other person better. How can you make that happen every time you see someone you want to talk to? Read on for 20 good ways to start a conversation with someone you don’t know!

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Introduce yourself. “Hi, I’m Rob”, is a great way to start. It’s real, it’s truthful and the polite response from her is to say “Hi, I’m Sarah.” Girls are wary of cheesy pick-up lines and no one wants to sound like they’re using one that’s been tried a thousand times before. Try an icebreaker that you’d do in “real” life and see where it takes you.

Ask what he’s having for dinner. Maybe you’re at a restaurant with a bar area that serves food, and you see a cute guy. An easy and not-too-risky way to start a conversation is to ask about that yummy-looking entrée he’s eating.

“How about those Yankees?!” Finding a common interest – or one relevant to your environment – is always a good option. If it’s a sports bar, or just somewhere that the TV is showing a game, if you’re a baseball fan (or, season-permitting, a football/hockey/basketball fan), seeing someone you want to talk to, who’s into the game too, is a perfect conversation starter.

Speaking of common interests, if you see someone who catches your eye, with a book or a stack of papers in front of him at dinner, it can be a great way to start talking. Mention that you’ve had a busy day too, or ask what he thinks about the book he’s reading.


“Your dog is so cute! What kind is it?” Maybe you’ve seen her walking her puppy at the park and wanted to strike up a conversation. Most people with pets love to talk about their “best friends” and are open to this kind of approach.

“Is this seat taken?” If there’s an open seat next to that cute girl, ask if you can sit there! Next? Introduce yourself and see where things go.

“Great shoes!” Everyone loves to be complimented. Be sincere, pick out one specific thing you notice about him or her (her purse or shoes are unusual, he has a nice smile, you get the idea) and use it to start talking.

Send over a drink. This can work for both women and men, in the right setting. Want to break the ice but not sure how to do it? Buy her one and have the bartender deliver it, and let her know you were the giver! Then follow up by going over to introduce yourself.

Make a joke. Pop culture is full of references to use, and in the right setting any one might work. The bartender’s just broken three glasses in a row and you can mimic a perfect Homer Simpson “Duh!”? Good way to get a laugh and start talking.

Ask her opinion, if you’re a guy. Maybe you’re at a park and want a good lunch spot after you’re done hanging out, or maybe you’re at a bar with friends and want a great place for dancing later that night. If you see someone you want to talk to, this is a great icebreaker.

Ask for help, if you’re a girl. Need directions? Need a suggestion on your dinner spot after you finish cocktails? Ask that cute guy what he likes in the neighborhood.

Be unexpected. Asking an off-the-wall question can work when done right! She’s reading “Rolling Stone” and you remember a great cover from two years ago? Ask if she read that particular issue! See where talk goes from there.

Draw someone in as a third-person “expert.” For example, you and a friend are debating whether tab collars or button-down are better for dress shirts, or whether Guinness in a bottle is as good as it is on draft. Ask that cute girl nearby to settle the dispute.

Recent movies, concerts and restaurants are great conversation-starters. Did you see Van Halen on their recent tour, or are you about to visit that new museum exhibit at a local gallery? Ask her if she’s interested in music/arts/etc., too, and then explore common interests.

“Need another?” Whether it’s the local coffee shop or the neighborhood bar, if you see someone interesting and notice he or she’s running low, a “refill” can be the perfect way to strike up a chat.

Ask if she comes there often. You can do it without sounding cheesy! If that pretty girl you’re eyeing seems to know everyone around, ask her why it’s her favorite Mexican place or sandwich shop.

Get to know the bartenders. If you make friends in places you like, it’s a great way to help you start conversations! They’re probably happy to help you meet someone new.

“Did you grow up here?” Many of us live far from our hometowns. Others among us are locals! You never know until you ask, and if that cute girl or guy is interested in you, too, you can learn a lot with this question.

“How long have you lived here?” Like #18, this helps you figure out what you have in common and interesting differences between you.

“Can I have your number?” Best after you’ve tried some of #1 – 19, but definitely a way to take the conversation to the next level and see if the other person’s up for it, too!