How To Start A Conversation With A Guy – 30 Tips

how to start a conversation with a guy
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You’ve been eyeing up a cute guy for a while, and it’s time to take the next step. “How to start a conversation with a guy?”, you wonder. Well, we’re here to tell you that all it’s going to take is a little courage, a lot of interest, and your truest self. When trying to talk to a guy, you’re probably worried about saying the right things, asking interesting questions, and wanting to seem charming in the way you talk to him. 

Trust us, it’s really not that hard. In a nutshell, the answer to how to start a conversation with a guy is that it’s just like starting a conversation with anybody else. Though it may seem like the hardest thing in the world, the minute you get a reply to the first message you send, you’ll realize it’s really not as big a deal as you made it out to be.

There’s a host of things you can bring up, questions that you can ask, or commonalities you can talk about. To help you get the ball rolling, we list out how you can start a conversation with a guy over texts, calls, or any other way you prefer.

30 Tips On How To Start A Conversation With A Guy 

You might be thinking, “I wanted to start a WhatsApp conversation with a guy, but I just had no idea what to say.” Unless you’ve never talked to this person before, starting a random conversation with someone won’t really seem that out of the blue to the recipient. Just because you’ve given this a lot more importance in your head than you should’ve, doesn’t mean it’s actually a life or death situation.

When you’re thinking about how to start a conversation with a guy, remember one important detail: it requires you to be your best, most unabashed self. It is only worth hitting it off with a guy if he gets to see you for who you actually are. Whether you’re chatting up a new guy at a party, in need of some tips for a first date, or just trying to make a friend at work, here are 30 tips on how to start a conversation with a guy: 

1. Start simple and straightforward

“I only love rainy days when I’m indoors. Are you enjoying the weather today?” This is a simple and effective answer to how to start a conversation with a guy. It’s also a conversation starter that can help you ease into a longer exchange. Start with something simple and fresh, even if you are discussing something as mundane as the weather. 

“Can you believe how hot it was in Seattle yesterday?” is another way you can start your conversation with a guy. It does not command immediate interest but will guarantee a response that you can build upon. 

Related Reading: Best Dating App Conversation Starters That Work Like A Charm

2. How to start a conversation with a guy you like? Music is a great ice-breaker 

“What are you listening to these days?” always helps break any first-talk awkwardness. Everyone enjoys different kinds of tunes, and it is always an engaging conversation to discuss musical genres. If you’re wondering how to start a conversation with a guy, you can ask him about his music preferences or who his favorite current artists are. 

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3. Send him a snap of what you’re doing 

If you’re trying to chat up a guy on text, you should probably send him a snap of what you’re doing at the time. It could just be a picture of your coffee mug, or your laptop to indicate your long workday, your dog, or your surroundings if you’re out somewhere. That is sure to start a back and forth of pictures and a cute conversation for you to get healthy flirting cues from. See, figuring out how to start a conversation with a guy online isn’t too hard, is it?

4. How to start a conversation with a boy on text? Compliment him! 

“That shirt really brings out the color of your eyes” or “Your new haircut looks fab!” are some things that you can use as conversation starters that are actually compliments. Believe us, men love compliments as much as women do, and they’re sure to respond with interest.

It’s undoubtedly one of the best things you can do to get his attention. If you’re looking to start a flirty conversation with a guy, compliment his physique. That’s bound to get the ball rolling. Moreover, he’ll be super glad that you noticed these little details about him. 

5. Play up your common interests 

“Hey, I saw on your Instagram that you went to Applebee’s last night! I love that place. Have you tried their mozzarella sticks?” Boom! Instant conversation and you’ve identified a common interest. If you don’t happen to come across a story or a post that suggests a commonality, you can always ask him what his hobbies are and try to see if you two have anything in common.

If you’re wondering how to DM a guy you’ve never talked to but know that you two have a shared love for books, start there. Find what you both like and enjoy together and get talking. Since WhatsApp also has stories now, this can also work when you’re figuring out how to start a WhatsApp conversation with a guy.

6. Reply to his stories 

Social media makes it easy to connect. Instagram and other social media apps with the Stories feature have made it very simple to figure out how to start a conversation with guys. If you like a guy’s story, you can simply respond to it with a short message to indicate that you want to talk to him. 

Even an emoji works in this situation. If he’s posted something funny, something as simple as sending across a laughing emoji can get you two talking. Replying to his story is quite literally the best answer to how to start a conversation with a guy online.

Related Reading: 5 Emojis Guys Send Their Girl When In Love

7. Ask outlandish questions

“What is the one food you simply cannot live without?” Go all out with the outlandish questions. Some other ones you can try are, “What is the craziest thing you have done?” or “Have you ever committed any minor crimes?” 

Online or on dating apps, these questions are all the rage to get to know somebody. You can also try some simple get-to-know-me questions to keep the conversation going. Similar to questions you would ask in a “Never Have I Ever” game, use these engaging bits to get him to tell you a thing or two. 

8. Meme your way into his heart

sending memes to start a WhatsApp conversation with a guy
Send him memes to make his day

Sending memes is the new Gen-Z practice to tell someone that you’re thinking of them. Even if you’re wondering how to start a conversation with a boy for the first time, memes can come to your rescue. Most importantly, it is also a lot of fun. If you want to start a conversation with a guy, these days it is as simple as sending a funny meme and you are good to go.

9. Netflix and chill? 

Ok, maybe don’t start with that, but, “What are you watching on Netflix these days?” is a totally relevant conversation starter, especially to get dates on Tinder or any other dating app. Or you can even say, “I just finished watching the show Lucifer and need something new to be hooked onto. Care to give me a recommendation?”

People love sharing pop-culture content that they enjoy so he will definitely enjoy talking to you about this one. If he’s cute and passionately nerdy about shows and web series, chances are he will give you some hot recommendations and talk about his interests with you. Instead of racking your brain over how to start a conversation with a boy, just ask him what he likes to watch.

10. How to start a conversation with a guy you like? Tattoo talk

When people get tattoos, they often have an interesting story and reason for getting them. If the guy has a tattoo, all you have to do is spot it and ask him about it. He would love to tell you his backstory if you show interest, and it’s definitely a cute question to ask your crush.

You could even ask where he got it, and say you’ve been thinking about getting one yourself. Chances are, he’ll ask you where you intend to get inked, with a naughty glint in his eye.

11. Talk about his pets

If you’re an animal lover, getting to know more about his pets is always the easiest way to get to know him better. If he is a pet parent, it’s safe to assume he likes animals just as much as you, and you already have the best topic of conversation you could ask for.

Once you two start talking about your pets, it’ll usually lead to a conversation about funny pet stories. You could even start a conversation with a guy on Instagram if he posts a picture of his pooch. How to start a conversation with a guy can literally sometimes depend on whether he has a puppy or not.

Related Reading: 13 Proven Ways To Get A Guy’s Attention

12. Respond to his dating profile bio 

If you’re starting a conversation with a guy on dating apps such as Tinder, it can be interesting to respond directly to something that is in his bio. This will also tell him that you actually paid attention to his profile and not just to his pictures. 

Has he mentioned that he loves to read? Ask him about his favorite book. Is he into sports? Ask him what team he supports. Did he mention that he likes The Office? Make sure you crack a “That’s what she said” joke. The secret to successfully starting a conversation with a guy online may lie in his dating profile.

13. Wondering how to start a conversation with a boy for the first time? Go old school 

One way to charm a guy in a conversation can be by simply introducing yourself to him. “Hi! I’m Alanna. I saw you sitting here and thought I’d come over and talk to you.” Trust us, nothing oozes confidence like this one. He will be swooning. 

14. Compare him to someone famous 

Something along the lines of “You look just like Ashton Kutcher from No Strings Attached”, but make it accurate. Chances are that if he’s heard it before, he will blush. If he has not, he will still ask you why you think so and probably ponder over it. Either way, you’ve made your move. 

15. Discuss your common friend 

discuss common friend to start a WhatsApp conversation with a gu
Discuss your common friend

If you’ve met a guy at a friend’s party or through a friend, you can approach him by asking how he knows your friend. That sure is to open up a treasure trove of stories that you two may start discussing. To keep it going, you can also ask him if he wants another drink. And if after this you’re wondering, “How to start a conversation with a boy on text?”, just text him, “Had a great time at the party that night. Want to catch up someday?” and you’re good to go.

16. Rely on those GIFs 

Social media has truly revolutionized online flirting. GIFs are hilarious and can convey messages wonderfully if you use the right one. They’re amazing icebreakers and usually incite positive responses. Don’t end up getting confused because of the sheer amount of GIFs available, though. Just pick the first funny one you see, and don’t think twice.

Start a WhatsApp conversation with a guy by sending him a funny meme, and you’re bound to get him laughing. If he replies with another GIF though, it’s probably best to send him texts after that.

17. Negging is not a good idea 

A lot of people think negging can be subtle, fun, and flirtatious, but that’s not true. Negging is when you use a backhanded compliment that can confuse people and undermine their confidence. Even if some people are thick-skinned, it just does not work for everyone. So, steer clear if you’re serious about how to start a conversation with a guy, and do not use it as one of your Tinder openers.

18. Don’t keep your replies too short 

“Oh, fun!”, or “Nice to hear” are responses that you may not always get a quick reply to. Your response should always have bait for a follow-up conversation or a new topic that you can start. While short and sweet is the way to go, too short might just kill the conversation completely. 

Before you send a text, ask yourself how you’d reply to it if you were on the receiving end. Once you realize it’s hard to reply to “Nice”, you’re probably not going to use it too often. A simple tip: always follow your replies with “What about you?” and you’re good to go. For example, “Yeah, I like to read. What about you?” When you start a conversation with a guy over text, it’s important to keep him engaged.

19. “Looks fancy, what are you drinking?” 

In person or at a party, when you want to approach a guy and he’s not drinking an obvious beer, you can go over and ask him what’s in his glass. If you’re lucky, he will let you try his drink and maybe even ask if you want the same one. How to start a conversation with a guy just relies on you being a bit confident.

20. Comment on his photos 

One way to start a conversation with a guy on Facebook or Instagram is by commenting on his pictures and complimenting him a bit. It does not necessarily have to be a photo of him. It could be a photo of him on a surfboard or any other update in his life. You can comment and ask, “The water looks beautiful! Where was this picture taken?” 

21. “Oh I’ve read that book. You should totally try it!” 

If you’ve spotted a cute guy in a library, you should ask him about the book he’s picked up or what he’s currently reading. Or you can also look at what he’s picked up and give him your opinion on it. This way, you can continue the conversation about your interests and preferences, and discuss your views on literature. 

Related Reading: 21 Best Relationship Books That Everyone Should Read

22. Try not to come off as too sexual 

Even if you’re texting a guy you want to hook up with, don’t make it too obvious right off the bat. Get to know him a little before you really start to come on strong. While some sexual innuendos can really storm it up, too many will do just the opposite. They could turn him off or make him unnecessarily aggressive. Be careful about how far you go when you’re flirting with a guy. 

23. Comment on the situation and surroundings

How to make conversation with a guy is all about using the space that you are in wisely. If you’re at a garden party, you can mention how much you love the place and how beautiful it is. If you’re meeting at a farmer’s market, you can comment on what a busy day it is. Keep it simple and slowly rope him into the conversation. 

24. Keep it casual 

When you start talking to a guy, try to steer clear of any heavy or uncomfortable questions that may not be right at that moment. You don’t want to touch a nerve or make him conscious. Keep it simple, fun, and not too serious. Don’t straight up ask him about his problems, struggles, or so on. There is a different time and place for controversial relationship questions.

25. “I have to tell you the craziest story”

To keep him hooked on text, you can say this or bring up an interesting anecdote from the time you last hung out with him. It could be something from your childhood or even something you just experienced the day before. Not only will you be able to start a conversation with a guy online, but if your story is amusing, you’re probably going to make him laugh too.

26. When wondering how to start a conversation with a guy, bring up current events 

But don’t go too deep because you don’t know how interested or well-versed someone might be in these things. When something is common and very much in the news, people often always have some reaction to it. “Did you hear about the new Mayor’s faux pas the other day?” is a good way to get started. 

art of wooing

27. Offer help 

Offering help is a great way to appear likable and the person will instantly have a positive response to you. “I think you could use some help with those cartons” or “Do you need me to bring out the other files for you?” to a guy at work are some things that you can try. While you’re helping him, go ahead and flirt with your eyes just a little bit.

28. Ask him about sports 

With Americans being hugely passionate about sports, it’s hard to find someone who’s totally indifferent to it. “Did you watch the Lakers play last night?” or asking a guy what team he’s supporting in tonight’s game is a way you can get him pumped up and talking about his team. If you’re wondering how to start a conversation with a boy, you can always rely on sports.

Related Reading: 51 Impressive Second Date Ideas

29. “You seem like a writer to me, are you into poetry?”

If you’re approaching him in person for the very first time, you can try this subtle and flirty trick if you’re wondering how to start a conversation with a guy. Just comment on what you think he does or what vibe he is giving out. Even if he is the total opposite of what you guessed, this will still impress him. 

30. Have variety 

Don’t linger on one topic for far too long and keep an eye out for when the spark is fizzling out. If the conversation is losing momentum, hop onto another topic or ask him a new question. A conversation can quickly turn monotonous if you don’t keep working on it. Moreover, your attempts will quickly turn into flirting signs guys miss if he is not invested in the moment.

How To Start A Conversation With A Guy On Text Online

If you’re still a bit stuck on how to start a WhatsApp conversation with a guy or are wondering how to slide into his DMs, don’t worry, your anxiety is understandable. However, you must also acknowledge that you’re probably overthinking this whole scenario. How to start a conversation with a guy really isn’t that hard, especially if it’s online. Observe a few of the following points and see for yourself:

  • Reply to his story on his social media
  • Send him a meme or something relatable
  • Text him about something you know he likes and ask him follow-up questions
  • Send him a random snap of what you’re doing
  • Send him a funny GIF to get things started
  • Compliment him but follow it up with a conversation
  • Ask him about something on his dating profile, if you’re on a dating app
  • Ask him for a recommendation for a new series
  • Talk about a common interest you two may have
  • Ask him out on a date

Key Pointers

  • Starting a conversation with a guy isn’t too difficult, you just have to be confident and interesting 
  • You can try complimenting him, sending him a funny meme or even flirting with him
  • Talk about common interests, be interested in what he’s saying and steer the conversation into interesting topics 
  • Don’t overthink it, all you have to do is shoot your shot! 

How to start a conversation with a guy is really not rocket science. Guys are just as human as everyone else. All you need do is ignite their interest, gauge their personality and keep it light and fun. A little compliment here, a flirty text there, and you’ve already got him focused on you. And most of all, be yourself.


1. How do you text a guy first?

If you’re looking for an example of how to text a guy first, just go ahead and send him something like, “Hey! You seem like you’re into some good music. Got any recommendations for me?” or “I’m going to try my best to flirt with you now, but you know what they say, it takes two to tango.” How to start a conversation with a guy isn’t that hard, all you’ve got to do is just be confident.

2. How to start a conversation with a guy on Snapchat or Instagram?

The best way to start a conversation with a guy on social media is to reply to his stories. Or, you can send him a picture of what you’re doing or just randomly send him a funny meme or gif.

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