Starting a conversation with a guy you’re interested in really just comes down to finding a natural way in. You can comment on something you both see, offer a genuine compliment, or ask a question that actually makes him think. The secret is to be yourself and create a small opening that invites him to respond.
Breaking the Ice Without the Awkwardness
That first moment can feel like the highest hurdle, right? But it doesn't have to be so intimidating. Forget the generic advice—let's talk about practical strategies for making that first move, whether you're standing in the same room or connecting through a screen. The best approaches always feel confident and natural, never forced.
This infographic lays out three incredibly effective ways to kick things off.
Each of these methods—using your surroundings, giving a real compliment, or crafting a smart app opener—gives you a simple but powerful framework for starting a conversation that he'll actually remember.
Use Your Surroundings
Honestly, the easiest way to talk to a guy is by using what’s right there in front of you. A shared environment gives you an instant, low-pressure topic.
- At a coffee shop: "I always have trouble deciding here. What's your go-to drink?"
- At a concert: "They've been amazing so far! Have you seen them live before?"
- In a class or at work: "That project was surprisingly tricky. How did you find the last part?"
This approach works because it’s observational, not personal. You aren't putting him on the spot; you're just inviting him into a brief, shared experience. It’s one of the most effective and good conversation starters with guys precisely because it feels so organic.
Give a Genuine Compliment
A specific, well-placed compliment can be ridiculously effective. Just skip the generic lines like "You're cute" and go for something more personal and observant. It shows you’re actually paying attention.
For instance, instead of a simple comment on his looks, try something like, "That's a really cool band on your t-shirt. I love their music." This immediately opens the door for him to talk about his interests, making the whole interaction more engaging from the get-go.
The goal of a great first compliment isn’t just to flatter him. It’s to spark an immediate connection based on a shared interest or a specific detail you genuinely noticed. That's what makes your approach feel authentic and memorable.
Craft the Perfect App Opener
Dating apps have completely changed the game. Today, with over 350 million people using them worldwide, crafting an opening message that stands out is absolutely essential. In the U.S. alone, about 30% of adults have tried online dating, so it's a super common place to make the first move.
The key to online openers is making them personal. It shows you actually took a second to see who he is.
A simple "Hey" gets lost in the noise. Instead, try digging into his profile for a unique angle:
- "Your pictures from your hiking trip in Peru look incredible! What was the best part of that adventure?"
- "I see you're also a fan of classic sci-fi movies. What’s your all-time favorite?"
This approach proves you’ve read his profile and are interested in more than just his photos. Plus, it gives him something easy and interesting to respond to, setting the stage for a real conversation.
Conversation Starters Online vs In-Person
Starting a chat in a DM is a totally different ballgame than approaching someone at a bar. What works in one scenario can fall completely flat in another. Knowing the difference is key to making a great first impression, wherever you are.
| Scenario | Ineffective Opener | Effective Opener | Why It Works |
|---|---|---|---|
| Dating App | "Hey" or "Hi" | "Your dog is so cute! What's their name?" | It's personal, references their profile, and asks a simple question. |
| In-Person (Bar) | "Do you come here often?" | "This band is great. Have you heard them before?" | It's about a shared experience, making it feel natural and low-pressure. |
| Dating App | "You're hot." | "That's a cool tattoo. Does it have a story behind it?" | It's a specific compliment that invites a longer, more personal response. |
| In-Person (Coffee Shop) | (Silence) | "Sorry to interrupt, but is that the new fantasy novel everyone's talking about?" | It shows you have a shared interest and creates an instant, easy topic. |
Ultimately, the goal is the same whether you're typing or talking: create a connection. The best openers, online or off, are the ones that feel genuine to you and give the other person a reason to want to keep the conversation going.
Keeping the Conversation Flowing Naturally
You’ve broken the ice. Amazing! But that first moment is just the starting line.
The real challenge—and the real art—of talking to a guy you like is keeping the dialogue going long after that first hello. We all know that dreaded fizzle, where the small talk just… stops. Dead end. Awkward silence.
There’s actually a simple framework I love for this: ask, share, connect. It’s a game-changer for keeping the conversational ball rolling without it feeling like a Q&A session.
You ask a good question, share a little something about yourself in return, and then find a way to connect the dots between your two experiences. This creates a natural back-and-forth that feels more like you’re discovering things together, not just interviewing him.
Ask Better Questions
If you want to keep a conversation alive, you have to move past the boring, surface-level stuff. Ditch any question that can be answered with a single word. Think beyond, "How was your day?"
Instead, try some of these swaps to get a real conversation going:
- Instead of: "Do you like movies?"
- Ask: "What’s a movie that you could watch over and over again?"
- Instead of: "What do you do for work?"
- Ask: "What’s the most interesting project you’ve worked on recently?"
- Instead of: "Have you been busy?"
- Ask: "What’s been the highlight of your week so far?"
These kinds of questions invite him to share a piece of his personality and what he’s truly passionate about. Suddenly, you have so much more to work with.
Share a Piece of Yourself
Once he answers, it’s your turn. This is crucial. Sharing a relevant story or opinion shows you’re actually in the conversation, not just directing it. It’s what makes the interaction feel mutual and builds a foundation of trust.
Let's say he mentions a recent hiking trip. Here’s how you can jump in.
Him: "I went hiking up at the national park last weekend. The view from the top was incredible."
You: "That sounds amazing! I went hiking there last fall and was blown away by the colors. I’m always looking for new trails—did you find any hidden gems?"
See what happened there? You validated his experience, shared a quick, related story of your own, and then tossed the ball back to him with another open-ended question. Smooth.
Find the Connection Point
The final piece of the puzzle is to highlight what you have in common. This is the moment a simple chat starts to feel like a real connection. Pointing out a shared interest, a similar experience, or even a mutual perspective is what solidifies your bond.
In our hiking example, the obvious connection is a shared love for the outdoors. You can easily build on this. You could talk about other favorite trails, dream travel spots, or other outdoor hobbies. This shared interest becomes an anchor you can always come back to.
Keeping this flow going is even more important when you’re talking online or on an app. Research into communication patterns shows that dating app users are willing to invest real time into conversations that feel like they're building a genuine connection. You can check out more stats on how users engage on dating platforms at jploft.com.
Whether you’re chatting online or standing face-to-face, the goal is always the same: make the exchange feel meaningful. Show him you’re genuinely interested in getting to know the person behind the surface-level facts.
Decoding His Signals and Showing Your Interest
Okay, so the conversation is flowing. Awesome. You’ve moved past the initial awkwardness, and now you’re in that exciting, slightly nerve-wracking space where you’re trying to figure out… is he into this, too?
This is where the real dance begins. It’s all about reading the subtle cues he’s sending while confidently dropping a few of your own. It can feel like you’re trying to solve a puzzle, but honestly, most guys aren't as mysterious as they seem. You just have to know what to look for.
Reading His Green Lights
Is he leaning in when you’re talking? Or finding little reasons to keep the chat going when there's a natural lull? These are the classic, unspoken signs that he's hooked. Pay attention to his body language and the small things he does—they’ll tell you everything you need to know about how he’s feeling.
Here are some of the most common signs a guy is interested:
- Mirroring Your Body Language: If you rest your chin on your hand, watch to see if he does something similar a few moments later. It’s a totally subconscious thing people do when they feel a connection. It’s his brain’s way of saying, “Hey, we’re on the same wavelength.”
- Asking Thoughtful Follow-up Questions: He isn’t just nodding and waiting for his turn to speak. He’s digging deeper, asking why you felt a certain way or how you got into a hobby. This shows he’s genuinely curious about who you are.
- Mentioning Future Plans: This is a big one. He might casually drop something like, "We should check out that new coffee shop sometime," or "You’d love the band that's playing downtown next week." He's testing the waters and picturing you in his life, even in a small way.
Spotting these signals is your cue to reciprocate. When you see him showing interest, it's the perfect green light to express your own enthusiasm without feeling like you're taking a huge risk.
How to Show You're Interested
Now it's your turn to send a few signals back his way. Showing your interest doesn't mean you have to be super bold or aggressive. It's more about making him feel seen, appreciated, and giving him the green light to keep things going.
A sincere compliment is always a great place to start, especially one that goes beyond his looks. Try something like, “I love the way your face lights up when you talk about your work; you're clearly so passionate about it.” It shows you’re paying attention on a much deeper level.
A little bit of light-hearted teasing can also work wonders for building a fun, flirty vibe. If he tells a cheesy joke, you could flash a smile and say, "Okay, that was terrible… but I’ll let it slide this time." This creates a playful dynamic and a little inside joke just between the two of you.
Most importantly, just show your enthusiasm. When he’s telling a story, react! Simple phrases can make all the difference:
- "No way, you have to tell me more about that!"
- "That’s actually really cool. How did you get into that?"
These little affirmations make it clear that you're enjoying the conversation just as much as he is and open the door for a much deeper connection.
Transitioning from Talking to a Real Date
The conversation is flowing, you're both laughing, and you can feel a genuine connection sparking. This is that perfect little window of opportunity to bridge the gap between just talking and actually meeting up. The trick is to make it feel like the most natural next step in the world, not some sudden, high-stakes proposal.
Timing really is everything here. You don’t want to jump the gun, but you also don’t want to let that amazing momentum fizzle out into the friend zone. A golden opportunity to suggest a date is right after he’s shared something he’s passionate about, or you’ve just discovered a mutual interest. It makes your suggestion feel thoughtful and directly tied to the bond you’re building.
Proposing a Low-Pressure Date
Steer clear of vague invitations like, "We should hang out sometime." Let's be honest, vague plans usually turn into no plans at all. Instead, come up with something specific, totally low-pressure, and super easy for him to say "yes" to. You want it to sound fun and casual, wiping out any potential for awkwardness.
Good first date ideas often involve an activity. It takes the pressure off trying to keep the conversation going nonstop.
- Grabbing coffee: It's a classic for a reason. A coffee date is short, casual, and can easily turn into something longer if you're both feeling it.
- Visiting a local market: A farmers' market or a cool flea market gives you tons of things to look at and chat about.
- Going for a walk: A simple walk in a nice park is as relaxed as it gets—and it's completely free.
The absolute best date suggestions tie back to something you've already talked about. It shows you’re not just asking him out; you're asking him out because you've been listening and genuinely want to explore a shared interest together.
For example, if he mentioned he loves old bookstores, you’ve got the perfect opening. You could say something like, "You mentioned you're a big fan of old bookstores. There's this really cool one downtown I've been meaning to check out. Want to go with me this weekend?"
This approach is so effective for a few key reasons. It's confident and direct, but because it's tied to his interests, it feels incredibly personal. You aren't just asking for a date; you're suggesting a shared experience based on your conversation.
For a deeper dive on making your move, our guide on how to ask a guy to hang out has even more tips. By suggesting a specific plan, you take all the guesswork out of it for him, making it way easier to get an enthusiastic "yes!"
Building Unshakeable Confidence
Okay, before you even start worrying about the perfect thing to say, let's talk about the real first step. It all starts with you. The biggest thing that holds us back is usually the fear of rejection, right? It builds this huge mental wall before we even get a chance to say "hi."
That little voice in your head starts spiraling. "What if I say something dumb?" or "What if he's not even interested?" It's enough to make you give up before you start.
But what if you thought about rejection differently? It’s not a personal attack. It's not a judgment on whether you're cool or attractive enough. All it is is a compatibility filter. If he’s not into it, you just weren’t a match. That actually saves you both a ton of time and energy.
Rejection isn't a judgment—it's just information. It tells you that this specific connection isn't the right one, freeing you up to find one that is. Seeing it this way removes the sting and empowers you to act without fear.
When you can approach someone from a place of genuine self-assurance, it changes the entire vibe of the conversation. Your mindset really does set the tone for everything that follows.
Cultivate Your Inner Confidence
Confidence isn't this magical thing you're either born with or you're not. It's something you build, piece by piece. It comes from truly knowing your own worth, completely separate from what anyone else thinks about you. Knowing who you are and what you bring to the table is your secret weapon when you're figuring out how to talk to a guy you like.
A big part of this is just feeling good in your own skin. When you present yourself in a way that feels authentic and comfortable, it gives you a major boost. For example, learning about dressing to flatter your body type can make you feel more put-together and poised before a single word is exchanged.
Here are a few practical things you can do to pump yourself up before you make your move:
- Mindful Mantras: Seriously, try it. Start your day with something simple like, "I am worthy of a great conversation," or "I am interesting and engaging." It sounds a little cheesy, but it genuinely helps shift your mindset from nervous to ready.
- Recall Past Successes: Take a second to remember a time you felt totally on top of your game. Maybe it was nailing a presentation at work or just a time you felt awesome with your friends. Channel that feeling. You've been confident and capable before, and you can be again.
- Focus on Your Strengths: Quick, list three things you actually like about yourself. Your killer sense of humor? The fact that you're a super loyal friend? Your passion for vintage sci-fi movies? Remind yourself of what makes you, you.
These aren't huge, life-altering changes. They're small exercises that ground you in your own value. It makes approaching someone feel less like a high-stakes performance and more like a simple, authentic interaction.
Ultimately, that unshakeable confidence is built over time through small, consistent actions. If you want to dig deeper, our guide on how to be more confident socially has a ton of other practical tips. The goal is to walk into any conversation knowing your worth isn't up for debate—you're just seeing if there’s a connection.
How to Revive a Stalled Conversation
It happens to the best of us. You’ve nailed the opening line, the banter is flowing, and then… crickets. The energy just dips, his replies get shorter, and you're left staring at your screen wondering, "Well, now what?"
First, don't panic. This is completely normal. Having a few tricks up your sleeve for these moments is a huge part of learning how to talk to a guy you like with real confidence.
This isn't about trying to force a conversation that's clearly over. It's about learning how to skillfully steer through a temporary lull to see if there’s still something there. The goal is simple: either reignite that initial spark or gracefully let it fade without feeling like you failed.
Pivot to a New Topic
Sometimes, a topic just naturally runs out of gas. If you’ve been dissecting your workdays for the past 10 minutes, it’s no surprise that the conversation might hit a wall. This is the perfect moment for a smooth change of subject.
The trick is to make the transition feel organic, not abrupt. A simple pivot phrase that loosely connects to what you were just talking about works wonders.
Try one of these:
- “That actually reminds me of something funny that happened…”
- “Speaking of busy weeks, are you doing anything fun this weekend?”
- “Random question, but have you seen [popular new movie/show] yet?”
This approach gently closes the door on one topic while opening a fresh one for him to walk through. It keeps the momentum going without that dreaded awkward silence.
Ask a Re-Engagement Question
Okay, so a simple pivot didn't quite do the trick. Time to bring out a slightly stronger tool: the re-engagement question. This is a specific type of open-ended question designed to inject a little more energy and personality back into the chat. It's usually a bit more playful, hypothetical, or personal.
Think of a re-engagement question as a mini-restart button. It shifts the conversation away from basic facts and invites him to share an opinion, a memory, or a dream—all of which are way more interesting.
Instead of another question about his day, give one of these a shot:
- “What’s one thing you’re genuinely excited about right now?”
- “If you could have any superpower, what would it be and why?”
- “What’s the best concert you’ve ever been to?”
Questions like these require more than a one-word answer and can tell you so much more about who he is.
But finally, and this is important, you have to know when to let a conversation die a natural death. If you've tried a pivot and a re-engagement question and you're still getting one-word, low-effort replies, it might just be time to let it go. Not every chat is meant to turn into an epic, hours-long connection, and that is perfectly okay.
What If He… Or I…
Even with the best game plan, things can get awkward. It happens. You might clam up, or he might not give you much to work with. Here are a couple of the most common situations I get asked about and how to handle them without totally losing your cool.
What if I Get Really Shy When I Try to Talk to Him?
Oh, this is a big one. Your heart starts pounding, your palms get sweaty, and suddenly you’ve forgotten every interesting thing you’ve ever thought. We’ve all been there.
The trick is to lower the stakes. Don’t try to have the world's most amazing conversation right off the bat. Start somewhere you feel more comfortable, like shooting him a DM about a story he posted or bringing him into a conversation with a mutual friend. The pressure is way lower in a group setting or online.
Before you even approach him, have one or two open-ended questions in your back pocket. Just one! Something simple like, "What have you been listening to lately?" or "Any big plans for the weekend?" can get the ball rolling without you having to do all the work.
And remember, it’s completely okay to be a better listener than a talker. In fact, most guys love it. Showing you’re genuinely interested in what he’s saying is often way more compelling than dominating the conversation.
How Do I Handle One-Word Answers?
Ugh, the dreaded one-word reply. It’s like hitting a conversational brick wall. You ask a great question, and all you get back is "yeah," "cool," or "nothing."
This could mean a few different things. He might just be busy, maybe he’s naturally a bit shy himself, or—and this is the tough one—he might not be interested. Before you bail, it’s worth giving it one more shot with a really good open-ended question that he literally can't answer with a "yes" or "no."
Something like, "What was the best part of your trip?" is much harder to shut down than "Did you have a good trip?"
If the short replies keep coming after that, it’s probably your cue to redirect your energy. Honestly, trying to force a connection that isn't there is one of the most draining things you can do.
Here’s the thing: Someone's communication style tells you a lot. If he's consistently giving you nothing to work with, that’s your answer. It's so much better to move on than to keep pushing a conversation that isn't flowing.