First of all, take a breath. It’s really not that deep. Talking to a guy is just talking to a human—one who probably isn’t analyzing your every syllable like you think he is. If you can chat with your friends about which pizza toppings are acceptable (pineapple is a whole debate), you can definitely start a conversation with a guy.
Start with the basics
You don’t have to launch into a mind-blowing opening line. A simple “Hey, how’s it going?” works just fine. The key is to sound natural, not like you rehearsed a TED Talk in front of your mirror. If you’re in a social setting, commenting on something around you is an easy way in. “This music is way too loud” or “That dog over there is living its best life” gives you a shared moment to talk about.
If you’re dealing with a guy you already kind of know (like a coworker or someone from class), something specific helps. “Hey, did you see the game last night?” or “How’s that project coming along?” makes it feel more like a normal chat and less like a mission.
Use humor (even if it’s corny)
A little humor goes a long way. No, you don’t need a full stand-up routine, but a light joke makes the conversation feel easy. If he’s holding a ridiculously complicated coffee order, you could say, “Wow, that’s a commitment. Is this your usual, or are you just feeling bold today?”
People like to laugh, and a guy who enjoys your humor will likely want to keep talking to you. Plus, even if your joke flops, that awkward little moment can actually be charming.
Ask something simple
Questions are great because they take the pressure off you to keep talking. But—and this is important—don’t turn it into an interrogation. Keep it light. “What’s your favorite kind of food?” is a lot easier to answer than “What’s your five-year plan?”
If he gives short answers, don’t panic. Some guys need a little warming up. If he seems interested but just isn’t a big talker, try a follow-up: “Okay, but if you could only eat one food for the rest of your life, what would it be?” This keeps it fun and easy to build on.
Read the room
Not every guy is in a chatty mood all the time. If he seems distracted, gives one-word answers, or looks like he’s about to escape, don’t force it. It’s not necessarily about you—maybe he’s having a rough day, or maybe he’s just not the talkative type. Either way, that’s fine. You’re looking for a conversation, not an interrogation.
On the flip side, if he’s engaging, asking you questions back, and generally keeping the conversation going, congrats! You’re doing great. Keep the energy going and don’t stress about what to say next. Let it flow naturally.
Use compliments (but keep it casual)
Compliments can be a great conversation starter, but there’s an art to it. A simple “Cool jacket” or “I like your sneakers” is enough to get the ball rolling. It feels natural and doesn’t put too much weight on the moment.
The key is to avoid overdoing it. Saying, “Wow, you have the most amazing eyes I’ve ever seen,” might sound intense if you’ve just met. Keep it light, and if he responds well, the conversation can build from there.
Don’t overthink it
The biggest mistake? Getting so caught up in your head that you psych yourself out before you even say a word. The truth is, most people are just happy when someone makes the effort to talk to them. Worst-case scenario? The conversation fizzles out, and life goes on. Best-case scenario? You hit it off and end up with a fun new connection.
Think about all the times someone randomly started talking to you—at a coffee shop, in line somewhere, at a party. Did you analyze every word they said? Probably not. You just responded, and the chat went where it went. The same logic applies here.
What if you’re shy?
If you’re not naturally chatty, that’s okay. You don’t have to suddenly become the life of the party. The trick is to lean into what feels comfortable. Maybe you start with a simple question or a casual remark about something around you. The goal isn’t to impress anyone—it’s just to start talking.
Also, body language helps. A friendly smile, eye contact, and an open posture (aka not crossing your arms like you’re bracing for impact) make you look approachable. Sometimes, that alone is enough to invite a conversation.
It’s just a conversation
At the end of the day, talking to a guy is just that—talking. It’s not a job interview, it’s not a life-or-death situation, and it definitely shouldn’t feel like a performance. The more relaxed you are, the easier it’ll be. So take a breath, say something simple, and see where it goes.And hey, if it doesn’t go anywhere, there’s always chocolate. Chocolate is self-care.