Top 20 Smooth Conversation Starters With Strangers

Picture this: it’s your middle school orientation, you’re ready to start a new chapter, and you’re completely terrified. That was me about fourteen years ago. I didn’t know who my friends would be or where I would fit in. And then I saw another girl, alone like me, and though the thought made my stomach tangle into a ball of knots, I went right up to her, stuck my hand out, and said, “Hi, I’m Jamie. What’s your name?” Not the smoothest, but not the clunkiest either. She wasn’t mean. She didn’t tease me. She didn’t point and laugh at my face. Instead, she simply responded, “Hi, I’m Shannon.” We didn’t become best friends forever or any cheesy moral like that, but that day, because of that short conversation, we were always friendly. And we were always kind to each other, even throughout high school. That’s the first time I remember starting a conversation with a stranger. And now, I’m a bartender, where it’s basically my job to start conversations with strangers. So from one professional conversationalist to a stranger, here are the top 20 smooth conversation starters to use with strangers.

Break the ice. Get 'er done. Go for it. Set the example. Start the conversation. If you’re alone and they’re alone, they probably want to chat with someone also. Humans are social creatures, always vying for connections with others. Stranger danger doesn’t last forever, folks. Now of course, only approach safe strangers and make sure to read the situation. If you’re both at the bar, drinking your respective cocktails and just scrolling through your Facebook feeds, you’re probably both open to chat. But if you’re at a library and the object of your attention is writing or reading a book, they may not want to be approached… although…

You’d be surprised how many people come into the bar to just sit and read with a beer (or an old-fashioned… welcome to the post-Mad Men era). People who enjoy reading books typically enjoy conversations about books, too. Plus, it’s a great way to get a feel for their tastes and tendencies. You can learn a lot about a person by what they read, and it gives you a lot to bounce off of. For example, if they’re reading Harry Potter and the Half-Blood Prince for the seventh time, you can talk about anything in the Magical World of Witchcraft and Wizardry, as well as the fact that the sixth book is the superior book in the series. Now, if they’re reading it for the first time… no, that’s impossible, everyone’s read the series, right? In all seriousness, someone’s taste in books can open up infinite doors of conversation. Lean into the old-fashioned way to meet people, physical copies of books, and leave the online world behind!

Never underestimate the power of, “The weather is amazing today! I can’t believe it’s 70 degrees in the middle of February in New York City.” This is real. As a bartender, one of the first conversations I have with every stranger is about the weather. For example, “How’s the rainy day treating you?” “Ah, it’s not so bad. Definitely not like yesterday, though.” “Yeah, yesterday was beautiful! I’m pretty sure the world is ending, but I definitely do not mind.” From there you can have a conversation about what you both did yesterday or the last time you remember being in the beautiful sunshine, or even about climate change and politics if you’re up for it.

People like sharing their opinions. They like talking about things they care about. And you can usually get there by asking their opinion on something. If you see text scroll across a TV screen at a bar, reading something like, “Man Claims to See U.F.O.” you can say to your stranger, “Do you think he really saw a U.F.O.? What do you think it could be?” Then you can talk weird conspiracy theories.

What movies do they like? Do they prefer iMessage or Whatsapp? Why? Do they watch Netflix? Listen to podcasts? Go running? Climb mountains? Fly to outer space? Try your best to stay on topic, though. You don’t want to come off as interrogative, just curious and interested in their life.

How would you feel if you were texting someone or sending them a WhatsApp message, and they continued the conversation by asking a lot of random questions but not responding to what you actually had to say? It’d be kind of weird right? It’s much clearer to see that with text on a screen, but in person, these things can get a little muggier. It can be easy to zone out, but if you really care about making conversation with this stranger, listen to what they have to say, and respond appropriately - acknowledge what they said, and add your own opinion to the conversation!

I don’t mean, “Wow, I love your bracelet, where’d you get it?” Regina George style, but if you want to have a conversation with this stranger, there’s clearly something drawing you to them. What is it? Is it their mermaid-dyed hair? Their floral printed pants? Their Clark Kent-style spectacles? Plus, everyone loves a compliment. Sharing a compliment starts the conversation off on a positive note, and opens up a chat about what the other person likes, where they go, and what they do.

For example, “Hey it’s three o’clock on a Tuesday and we’re both here in this bar, what do you do?” Easy! Much easier than trying to find and look through the entirety of the Facebook profile of a potential Tinder match. And if they say something like, “I’m an engineer for a company in which I go to people’s homes and figure out if everything is working properly,” and you’re like, “I’m an elementary school teacher and the most advanced mathematics we do are fractions,” you may think you have little in common. But, this is only an opportunity to learn something new! Take the conversation and run with it.

This keeps the conversation comfortable and friendly. Obviously don’t go up to a stranger and be like, “Guess what? I ate an entire tub of ice cream last night all by myself.” Although if you did, more power to you, eat that ice cream up like a slew of Facebook messages from your middle school crush. But, that might be a little much to share upon your entering approach. Instead, for example, if there’s a song on overhead, you could say something like, “Wow, I love this song! This is actually my go-to karaoke song. Well, basically anything Katy Perry is my go-to. Do you ever do karaoke?” This not only reveals something fun and quirky about yourself but is able to bring it back to asking a question to your stranger. By leaving the last thing you said open-ended, it allows the conversation to continue. It always comes back to questions.

Don’t be afraid to let your true self shine through! We all think weird thoughts (right?) and do things that are a little silly and different from most other people. Pointing out these things shows you’re comfortable in your own skin and you can laugh at yourself. For example, I met a guy when I was travelling and in our first conversation, I told him all about how I will get home after a night out and drunkenly fall asleep with peanut butter toast on top of me. That may not sound like the cutest trait a girl could have, but then he countered with one time he drunkenly fell asleep with pizza on himself, and it got all in his chest hairs! We had a good laugh and didn’t really feel like we were speaking stranger to stranger anymore.

Now, there are two types of teasing. There’s the type we try to avoid from ages five to eighteen, and then there’s the type we crave from age eighteen and up. And I’m not talking about the first type. I’m not talking about pointing at your stranger’s shoelaces and saying they’re untied, then smacking them in the nose. That’s for siblings, not strangers. (kidding, don’t do that to people.) I’m talking about the type of teasing when you see a person smoking a cigarette, you can say, “Hey, I hear that’s really bad for you,” and then pull out your own cigarette (if you’re a smoker. Don’t pick up smoking to impress a stranger.) Or like me, when I met this guy while travelling, I asked if he was cheating at a drinking game, like Tom Brady in football, knowing he's a Seahawks fan. Regardless, playfully teasing your stranger is a great way to get a conversation going.

Are they wearing a Mets hat? Start the conversation with, “You think Syndergaard’s going to come back in full force this season?” Or even something more basic like, “You a Mets fan? Same!” Or maybe they’re carrying a yoga mat, so you could ask, “Where do you go to yoga?” And consequently, chat about all the different types of yoga and the differences between the studios in your area. You may even end up exchanging info on Facebook or WhatsApp to hit up a yoga class or Mets game together!

Now, I’m not a huge proponent of talking to strangers online. I find face-to-face conversations to be much more telling as far as communicating via body language, facial expression, and vocal inflections. Online conversations are a whole other ballpark, especially when you haven’t yet met the stranger behind the screen. Whether you’re starting the conversation off on Tinder, or a friend connected you to one of their friends via Facebook, Whatsapp, or some other text messaging service, I strongly believe the best way to get a conversation going is to suggest meeting in person. Some people may be uncomfortable with this, especially on a dating app, but the only way you can really get to know someone and figure out if you’ll like them is face to face. So, I have two conversation starters for you based on the context: 1. Dating app - “Hey, I find it’s difficult to get a sense for people based solely on a screen. So let’s save the small talk for when we meet and pick a time and place *insert sassy girl emoji here*” and feel free to add a fun little GIF to toss in a piece of your personality to the conversation. 2. Networking/exchanging info via a Facebook friend, Whatsapp text, etc. - “Hey! *insert friend’s name* suggested we meet since we’re both active ladies in the comedy scene here. Want to go to a mic together sometime?” In both examples, you’re giving context for the urge to meet in person, as well as leaving it open to the other person to accept the invitation and add their own input.

Have you ever been in a situation where you’re at a party and Dylan Sprouse just happens to also be there, because you’re at NYU and it’s one of your friend's parties? No? Maybe someone less high-profile, like it’s an office party and the cute guy from the accounting department is there? One of the easiest ways to initiate a conversation with him is to see if any of your office friends know him. Someone is bound to if you’re all at the same party! Ask your friend to give you an introduction. After all, the most common way people meet their significant others nowadays is through a friend, so you never know what could happen.

What better way to start a conversation than by talking about the world around you? Start small… for example, If there’s music playing, “This is a great song! Do you know what song this is?” If there’s a game on the TV, “Which team are you rooting for?” If you’re at a friend’s birthday party and your friend is singing terrible karaoke, “Susan is so ridiculous, but I love her. How do you know Susan?” You get the picture. Open up a conversation by being observant, taking in the world around you, and finding something you can both chat about.

Do you ever see a stranger on the street, looking a little lost? Or inside a bar looking for the bathroom? Point them in the right direction! They’ll be thankful for your help, and be happy to have a short conversation with you. When I spent a year in Barcelona, I would often see confused American tourists. I knew they often didn’t speak Spanish and didn’t know who around them could speak English to answer their questions. I would often help them out in finding where they needed to go, and a short conversation would ensue about where they’re from, why I’m in Barcelona, and some things they might enjoy doing. One time, a few tourists even came out to a comedy show I was in that night! That was a few minutes of conversation well worth the time.

People love being helpful. It’s in our human nature to want to feel useful and necessary. Although it’s sometimes tough in a big city to just approach a stranger and ask for help, the payoff of having an interesting conversation with a stranger is well worth the risk of a little rejection. The worst thing that’ll happen is they’ll ignore you and continue about their day. One of the most memorable times a stranger started a conversation with me was when he was sitting in a convertible car on 80th St in New York City, and he asked if I knew where Calexico was. I told him and though I was on my way to work, he was able to continue the conversation by being funny and charming. Although I didn’t give him my number straight up (look, I don’t need strangers all over my WhatsApp feed), I did tell him where he can find me at work to keep the conversation going. He ended up coming to the bar I work at, where our conversation continued smoothly.

Similar to asking for help, asking for advice on a challenging life decision or situation can be a great way to start a conversation. For instance, imagine you’re at a bar. It’s not too loud. You’re trying to figure out how and if you should tell your friend that her boyfriend sucks. It’s a perfect way to begin the conversation. You can simply say to the stranger at the bar, “Hey, can I ask you for some advice? You seem like a fairly well-balanced person and I need an outsider’s perspective.” If they’re looking to converse back, this can be a great way to start off an interesting conversation, especially if you’re a person who prefers to skip the small talk.

Have you ever seen that scene in the movie, Heathers, where Heather goes around the cafeteria with a poll of the day, asking different students what they would do with five million dollars? That’s definitely one way into a conversation. It’s easier than you think to just approach a stranger and just say, “Hey, my friend and I are having an argument over which show is better, Parks and Rec or The Office. What do you think?” And if they’ve never seen either show, either they’re not worth the conversation, or you now have an opportunity share passionately your love for a couple of your favorite sitcoms.

Do you like playing soccer? Find a soccer league and play! And guess what? The other people you play with probably like soccer too. Same goes for any sport or physical activity, such as Zumba, hiking, skiing, etc. You aren't an outdoorsy person? That’s cool too. Do you enjoy painting, knitting, reading, watching movies? Find a club! Check out your local library for a book club, find Facebook groups dedicated to the thing you love or use meetup.com and couchsurfing to find activities you’re interested in where you can have conversations with strangers. Once at the activity, it’s easy! You can ask anyone there any number of things. For example, “How did you get into painting?” or, “How long have you played soccer?” The possible conversations you can have are endless.

Going up to that stranger in the bar isn't so bad after all. Whenever you feel that social anxiety, or get a feeling of heat wash over your body before saying hi to somebody, just remember humans thrive on making connections. Everyone's afraid to take that first step, but the worst that can happen is they don't want to talk. And then what? It is important to remember that just because someone is alone does not mean they want to talk. And sometimes, you can be as smooth as velvet, but you can't control people. If someone doesn't want to talk, just accept it, walk away, and find another stranger! The only thing that can hurt your chances is not going out at all. For more conversation tips, check out some of these articles: