If, like me, you learned your dating ABCs in the ’90s, you may wrestle with the idea of approaching a guy first.
This guide on how to start a conversation with a guy (and keep it going!) has all the answers, supported by my experience and some expert advice.
Best Ways to Start a Conversation With a Guy
Compliment his taste in music
People love being complimented on their taste in music, which is why it makes for such a great conversation starter.
You know, like that scene in 500 Days of Summer when Summer drops the “I love The Smiths” line in the elevator. Instant chemistry.
How about recreating that moment in real life?
So, if you notice his cool band T-shirt or overhear him talking about a concert, it’s the perfect opportunity to say, “Hey, I didn’t think anyone else was into Arctic Monkeys. What’s your favorite album?”
This invites him to engage in a non-invasive way.
Ask for his help (but be genuine)
I know you’re a strong, independent woman who doesn’t need a man, but . . . A little damsel in distress reenactment might just be the perfect way to start a conversation with that cute guy you’ve been eyeing at the airport. Isn’t your bag a bit too heavy anyway?
Research published in Clinical Psychological Science suggests that if we do small things for others, such as holding a door open for someone, we won’t feel as poorly on stressful days.[1]
So really, by asking him to help, you’re not just getting your bag lifted, you’re also making his day better. Win-win!
Whether it’s tech advice or reaching for something on the top shelf, giving him a chance to shine will make him feel valued. (And while I haven’t found a specific study on that part, I’m pretty sure it’s just human nature to want to help someone in need, especially when they’re as cute as you.)
Just remember to keep it genuine. People can always tell when you’re faking it!
Comment on the situation you’re both in
People naturally bond over shared experiences, whether it’s a concert, conference, or that one-time-you’re-both-waiting-forever-in-line-at-Starbucks scenario.
A study from Psychological Science explores how shared experiences, even difficult or painful ones, can enhance social bonding. This highlights how mutual experiences, especially those with some level of discomfort, can deepen connections and strengthen relationships.[2]
Try something like, “Do you think they are back there hand-picking the coffee beans?” A little humor helps break the ice and shows you’re laid-back.
Talk about his interests
One of the easiest ways to get a guy talking is to show interest in what he enjoys.
Research published in Psychological Science shows that people are more likely to be attracted to someone when they feel uniquely liked by them.
The study found that individuals who showed selective interest in someone, rather than being equally interested in everyone, were better liked and more likely to foster a reciprocal attraction.[3]
This suggests that by expressing a sincere curiosity about his passions, you’re indicating that you value him as an individual.
A quick, “I noticed you’re into basketball . . .” could get him chatting for hours. Plus, if it’s a passion of his, it’ll give you plenty of material to keep the conversation going.
Again, you need to be genuinely interested. If you’re only pretending to listen while your mind is elsewhere, don’t waste his/your time. Authenticity goes a long way in building meaningful connections.
Give him a lighthearted tease
If there’s one thing most people enjoy, it’s a little playful banter (within reason, of course).
Imagine you’re at a bar, and he’s playing pool. You throw out a flirty, “I bet I could beat you in two shots.” It’s fun, and a bit intense, but keeps the mood playful.
Now, personally, I’d never challenge anyone to a pool game, not only because I’d definitely lose, but also because it’s too bold of a move for me. But maybe you’re more daring than I am.
It really depends on the situation, and you’ve got to read the room. You don’t want to come across as too aggressive or brash, but if you’re both feeling it, go for it!
At the end of the day, whatever you do needs to feel genuine and authentic to who you are.
Teasing only works if it’s part of your personality, so don’t pretend to be someone you’re not. Keep it real, keep it fun, and most importantly, keep it you.
Topics to Talk About With a Guy
I’ve written a whole article on this, 25 Topics to Talk About With a Guy, with some example questions and prompts, so if you need more inspiration, go check it out, and for now, let’s explore five of my favorites.
Flirty debate topics
Flirty debates are a fun way to blend playful teasing with just the right amount of tension.
A study published in Evolutionary Psychology found that humor plays a significant role in romantic attraction (you don’t say). Men, in particular, tend to use humor to signal warmth, extroversion, and sociability, but it’s that magical moment of shared laughter that truly seals the deal.[4]
Funny debate topics are perfect for keeping things light while sneaking in a glimpse of how he thinks, how he handles confrontations, and what he values, especially when you’re “arguing” over the best dessert or passionately defending your choice in the classic cats vs. dogs debate.
Travel and world cultures
Talking about travel is the perfect gateway to uncovering how adventurous and curious someone is, and discussing other cultures can lead to some of the most fascinating revelations.
Maybe he’s been to Japan recently and has experienced the Kanamara Matsuri, that eyebrow-raising fertility festival with some rather unusual sculptures. What a subject to discuss!
So, ask him about his travel bucket list because swapping travel stories can spark some seriously fun and thought-provoking conversations.
Culinary experiences and gastronomy
Food is more than just sustenance — it’s culture, memory, and personality all in one.
We all remember that Friends episode where Ross has a meltdown over his leftover Thanksgiving sandwich. Food matters, and sometimes, it matters a lot.
Whether he’s into spicy street food or fine dining, talking about favorite dishes and culinary experiences can open up a whole world of conversation.
Ask him what his ultimate comfort food is or about a meal that holds a special meaning for him.
Skills and talents
Asking him about his skills and talents is fun for him because he gets to talk about what he’s good at, but it also gives you a sneak peek into his passions, strengths, and how he uniquely contributes to the world.
Interestingly, research published in Proceedings of the National Academy of Sciences shows that talking about oneself activates brain regions associated with pleasure, much like the rewards from food or money.[5]
So when he shares his particular set of skills or talents, he’s not only revealing what makes him tick but likely feeling pretty good while doing it!
Hypothetical scenarios and thought experiments
Hypothetical questions are like mental playgrounds, offering a glimpse into how someone handles abstract concepts and solves problems.
They also spark creativity and deeper discussions. One notable study, often referenced in discussions about creativity and problem-solving, is found in the 1992 book Creative Cognition. It highlights how people use mental imagery and thought experiments to generate and develop creative ideas.[6]
How to Keep a Conversation Going With a Guy
Ask open-ended questions
Open-ended questions invite longer, more thoughtful responses. Instead of “Did you like your weekend?” ask, “What was the best part of your weekend?” This prompts richer stories and keeps the dialogue alive.
According to The Fine Art of Small Talk by Debra Fine, “With creative usage of these three elements (questions, follow-up comments, follow-up questions), the possibilities and variations in conversation are virtually limitless.”[7]
It’s like choosing between skimming through a book quickly and diving deep into the juicy chapters of Outlander. Open-ended questions lead to deeper, more compelling dialogue, making the conversation far more engaging.
Share something about yourself
Reciprocity is the backbone of any meaningful conversation.
In a study published in the Handbook of Personal Relationships, reciprocal self-disclosure was found to significantly enhance feelings of connection between people.[8]
Sharing your own stories after he shares his helps create a sense of balance, which builds connection. You don’t need to overshare or jump straight into deep personal details — just share something relatable.
If he mentions his weekend hike, you could talk about your love for the outdoors, or if he’s into movies, mention that you have a MUBI subscription.
It’s about finding common ground to keep the conversation both balanced and interesting. Think of it like conversational tennis: If one person is serving, and the other is not returning, there is no interaction.
Use humor to keep things light
Humor is one of the most effective ways to create rapport and keep a conversation fun and lighthearted.
Whether it’s sharing a funny anecdote about your disastrous attempt at a DIY project or recalling how you binge-watched The Great British Bake Off and ended up burning your own batch of cookies, humor adds a playful vibe to the conversation.
This isn’t just about being a stand-up comic, though.
Gentle, self-deprecating humor or witty observations about everyday life can keep things flowing without the pressure to be too serious.
Reflect on what he says
Active listening is a subtle but powerful way to show someone you’re truly paying attention.
It’s not just about nodding or saying, “I hear you,” but understanding what they mean and reflecting it back.
A study published in the Journal of Counseling Psychology found that active listening significantly increases feelings of empathy and understanding between individuals.[9]
For example, if he talks about his love for mountain biking, instead of just saying, “Cool,” you might say, “It sounds like you love the thrill. What first got you into it?”
This keeps the conversation flowing and shows him that you’re genuinely interested, helping to create a deeper connection.
Be curious, not nosy
Curiosity can be a great way to keep a conversation engaging, but there’s a fine line between being curious and coming off as nosy.
A study published in the Journal of Personality and Social Psychology found that asking about someone’s hobbies or favorite activities increases the likelihood that they will open up and share more.[10]
You want to be more Jessica Day from New Girl rather than Agatha Christie’s Miss Jane Marple.
In the beginning, skip his family history or past relationships and stick to light topics like favorite sports, music, or travel experiences.
The goal is to make him feel at ease and understood, not like he’s being interrogated.
How to Start a Conversation With a Guy Over Text
Open with something casual
I personally believe there’s no need for a grand entrance with a text that feels like you spent 30 minutes agonizing over every word. That’s just giving intense. This is not Shakespeare in the Park — it’s Tinder. A simple “Hey, how’s it going?” can work like a charm.
How he responds to a super simple message speaks volumes about his level of engagement.
If he hits you with a “fine,” “k u,” or any of that half-hearted nonsense, it’s pretty clear he’s swiping out of boredom, to get his validation fix, and is not committed to actually finding a partner.
That’s not your cue to jump in and make things more interesting or “get him to like you.” He’s showing you exactly what he’s willing to give from the start — believe him.
The key is to keep it laid-back so you can guide the conversation wherever you want, without feeling the need to prove anything.
Reference something specific
When you’re starting a conversation on a dating app, referencing something from his profile is a go-to move.
It shows that you’ve actually read what he wrote, already putting you ahead of 90% of the swipers out there. Did he mention a recent trip to New York or his undying love for ‘90s action movies? Use that to your advantage.
You could go with something like, “So, how was the pizza in NYC? Did it live up to the hype or just rob your wallet?” A message like this does two things: It shows you’re paying attention and it helps kick the conversation off in a fun, personal way.
Referencing something specific, whether it’s his obsession with the Die Hard franchise or his passion for hiking, creates an instant connection.
When the conversation feels more personal, it’s easier to move things forward, and bonus points if it helps you spot the “meh” guys early.
If he can’t even remember what he wrote in his own bio, you know . . . But if he’s all in and ready to share more, congratulations, there’s something to work with.
Use a flirty opener
Flirting over text doesn’t need to feel like a cheesy rom-com (though, I’d totally pretend-date Matthew McConaughey in How to Lose a Guy in 10 Days).
If he claims he’s a finance bro, hit him with a finance-related pickup line, like, “Are we a good investment? Because I’m feeling some serious interest.” It’s fun, flirty, and just the right amount of cringe — which is exactly what pickup lines are supposed to be.
I love a cheesy pickup line! Pickup lines can be charming with the right dose of irony, and his reaction will tell you if your senses of humor click. Something like “Are you French? Because Eiffel for you” works when delivered with a wink and a grin.
The key is not taking yourself too seriously. You’re flirting, not auditioning for a rom-com.
If he’s into the playfulness, awesome — banter away!
Start with a playful question
To truly get to know a guy, you’ve got to ask him questions. But in the beginning, hit him with something quirky and unexpected, like, “Would you rather have a pet dragon or a pet unicorn?”
Or try a fun “never have I ever” statement. It’s a great way to kick off any conversation, whether it’s a conversation with someone you’ve just swiped right on or someone you know like the back of your hand.
Playful conversation starters create a relaxed, flirty vibe and help spark an instant connection.
In 10 Things I Hate About You, remember how Patrick and Kat banter back and forth in that cheeky way that just draws them closer?
You’re not diving into anything too deep yet, but you’re building a foundation of fun, witty interaction. Who knows?
You might discover he’s got a secret talent for impersonations or an irrational fear of lawn flamingos. Either way, you’re setting the stage for a conversation that could turn into something more, maybe even your own rom-com moment.
Reference a mutual interest
If you know he’s into something you’re equally obsessed with — whether it’s The Mandalorian, retro video games, or that mutual love for ‘90s hip-hop that’s all over his profile — this is your golden moment to go beyond basic small talk.
Shared interests are like conversational rocket fuel, taking you straight to the fun, engaging banter without the awkward getting-to-know-you phase.
You can slide in with something like, “What do you think about the new Mandalorian?” It’s casual and shows you’ve read his profile instead of just sending a generic, “Hey.”
It gives him the perfect opportunity to engage in something he’s into, which is basically the online dating equivalent of handing him the controller in your co-op video game.
You’ve set him up, now let him play.
And who knows, you might find yourself bonding over a nostalgic trip down memory lane with old-school Street Fighter moves.
How to Keep a Conversation Going With a Guy Over Text
Be playful
Playfulness is mentioned for the third time in this article because it’s that important!
When you’re texting a guy, especially one you’re interested in, a lighthearted approach works wonders.
Try tossing in a cheeky challenge like, “Bet you can’t guess what I’m doing right now (hint: it involves caffeine).”
Whether you’re texting a guy you met online or someone you’ve already had a few great conversations with, being playful helps keep the mood light and shows you don’t take yourself too seriously.
Remember, every guy enjoys a fun, engaging convo that keeps things interesting without getting too heavy too soon.
Respond in a timely manner
You’ve got a busy life, and so does he — nobody’s glued to their phone 24/7. But leaving a guy waiting too long can sometimes kill the momentum.
You don’t have to reply immediately, but finding that sweet spot between casual and interested is key.
Texting back in a reasonable time frame keeps the convo alive without feeling like either of you is playing mind games. It’s all about balance: enough space to keep your independence, but close enough to keep the rhythm going.
You don’t like being left on read for too long, and I’m pretty sure he doesn’t either.
Ask follow-up questions
When you’re talking to a guy over text, one of the best ways to keep the conversation going is by asking follow-up questions that go beyond small talk.
Let’s say he mentions he’s into something like hiking or kickboxing — this is your moment to dive deeper. Ask, “When did you start?” or “What’s the difference between kickboxing and Thai boxing?”
It shows genuine interest and helps you both move past the superficial.
Plus, this is a great way to see if you have common interests, or maybe even plan a hiking date down the line. Asking thoughtful, open-ended questions is a sure way to keep things interesting.
Know when to end the conversation
Sometimes, leaving a conversation on a high note is the best move. You don’t have to drag things out until you’re both exhausted from typing.
Knowing when to end the convo — like after a good laugh or an engaging topic — keeps him intrigued and looking forward to the next chat. Something as simple as, “I’ve got to run, but I’ll catch up with you later!” leaves the door open for future conversations without making it feel like you’re cutting him off.
It’s like leaving a dinner party before dessert — he’ll want more of your company next time instead of wishing you’d stop texting him.
Sprinkle in some mystery
There’s something incredibly captivating about a little mystery, especially when it comes to texting.
You don’t have to lay all your cards on the table in the first few conversations. Instead, give him a taste and leave him curious for more.
For instance, drop a line like, “I’ve got a great story about my last trip to Italy — remind me to tell you later.”
It adds an air of intrigue and keeps him engaged, eager to know more about you. Think of it as an elegant game of chess — move with intention and let him want to know you better one message at a time.
Conclusion
Knowing how to start a conversation with a guy may not feel intuitive, but if you show genuine interest, keep things light, and don’t overthink it, you’ll be chatting away like it’s second nature.
A mix of humor, curiosity, and confidence will get the conversation going, whether it’s in person or over text. I know it’s brutal out there, but you’ve got this!
Need help with starting a relationship? We’ve got all the tips — check out the link.
FAQ
How do I message a guy first?
To message a guy first, start the conversation with a fun opening line or casual question. Mention something relevant, like a meme or recent event, to get the conversation going and show you’re interested. Don’t forget to add emojis to keep it light and engaging.
How do I keep a guy interested over text?
To keep a guy interested over text, ask questions that let him share more about himself. Bring up common interests like books, shows, or a coffee shop you both like. Don’t just ask yes/no questions. Instead, ask him about his thoughts and follow up on his responses to keep the conversation flowing.
How do you introduce yourself to a guy through text?
To introduce yourself to a guy through text, keep it simple. Introduce yourself with a smile (via emoji) and ask something light to start, like a fun comment on the weather or a recent game. Let him know you’re genuinely interested in getting to know him better and use a conversational tone to show you’re approachable.
References
1. Raposa, E. B., Laws, H. B., & Ansell, E. B. (2016). Prosocial behavior mitigates the negative effects of stress in everyday life. Clinical Psychological Science, 4(4), 691–698.
https://doi.org/10.1177/2167702615611073
2. Bastian, B., Jetten, J., & Ferris, L. J. (2014). Pain as social glue: Shared pain increases cooperation. Psychological Science, 25(11), 2079–2085.
https://doi.org/10.1177/0956797614545886
3. Eastwick, P. W., Finkel, E. J., Mochon, D., & Ariely, D. (2007). Selective versus unselective romantic desire: Not all reciprocity is created equal. Psychological Science, 18(4), 317–319.
https://doi.org/10.1111/j.1467-9280.2007.01897.x
4. Hall, J. A. (2015). Sexual selection and humor in courtship: A case for warmth and extroversion. Evolutionary Psychology, 13(3).
https://doi.org/10.1177/1474704915598918
5. Tamir, D. I., & Mitchell, J. P. (2012). Disclosing information about the self is intrinsically rewarding. Proceedings of the National Academy of Sciences, 109(21), 8038–8043.
https://doi.org/10.1073/pnas.1202129109
6. Finke, R. A., Ward, T. B., & Smith, S. M. (1992). Creative cognition: Theory, research, and applications. The MIT Press.
7. Fine, D. (2005). The fine art of small talk: How to start a conversation, keep it going, build networking skills—and leave a positive impression! Hyperion.
8. Reis, H. T., & Shaver, P. (1988). Intimacy as an interpersonal process. In S. Duck, D. F. Hay, S. E. Hobfoll, W. Ickes, & B. M. Montgomery (Eds.), Handbook of personal relationships: Theory, research and interventions (pp. 367–389). John Wiley & Sons.
9. Weger, H., Castle Bell, G., Minei, E. M., & Robinson, M. C. (2010). The relative effectiveness of active listening in initial interactions. The Journal of Counseling Psychology, 57(3), 387–391.
https://doi.org/10.1037/a0018840
10. Kashdan, T. B., Gallagher, M. W., & Silvia, P. J. (2009). The curiosity and exploration inventory-II: Development, factor structure, and psychometrics. Journal of Research in Personality, 43(6), 987–998.
https://doi.org/10.1016/j.jrp.2009.04.011
