How To Start A Conversation With A Guy – 30 Tips

Dating experience | | , Expert Blogger
Updated On: September 22, 2023
how to start a conversation with a guy

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 there’s no one answer to how to approach a guy. 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.

Wondering how to make the first move on a guy? Well, there are a host of things to talk about with a guy, including 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

Are you up at night wondering, “I really like this guy but we barely even talk”? Or you might be thinking, “I want to start a WhatsApp conversation with a guy, but I have 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 doesn’t mean it’s actually a ‘life or death’ situation.

When you’re thinking about how to start talking to 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 really are. Whether you are chatting up a new guy at a social gathering, are in need of some tips for a first date, or are just trying to make a friend at your office, this article will help you with some tried and tested tips on how to strike up a conversation with a guy. So, let’s begin!

1. Reply to his stories 

Social media makes it easy to connect. Instagram and other social media apps with the ‘stories’ feature have made it quite simple to figure out how to start a conversation with guys you’re interested in. So, if you like a guy’s story on Facebook or Instagram, 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 or flirty emoji can get you two talking. Replying to his story is quite literally the best answer to how to begin a conversation with a guy on social media.

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

2. 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 mentioned in his bio. After all, be it guys or girls, people usually flaunt things that interest them on their dating profiles. This will also tell him that you’re actually paying attention to his profile and not just to his pictures. So, here are some tips:

  • 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 on the internet may lie in his dating profile.

3. Comment on his photos

One way to start a conversation with a guy on Instagram or Facebook 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 start by a simple comment, such as:

  • “The water looks beautiful! Where was this picture taken?”
  • “Wow! How do you always manage to go to such mind-blowing places?”
  • “Hey! This looks like [name of the place]. I was there last year.”

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

4. Meme your way into his heart

Gen-Z usually sends memes to tell someone they’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 on Instagram or other social media channels. 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

5. Ask outlandish questions

Wondering how to start a Snapchat conversation with a guy? Go all out with the outlandish questions, such as:

  • “What is the one food you simply cannot live without?”
  • “What is the craziest thing you have done?”      
  • “Have you ever committed any minor crime?” 

Such questions are all the rage, especially if you are up for dating online or want to impress a guy on social media. You can also try some simple get-to-know-me questions to keep the conversation going. There are 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.

Related Reading: 55 Best Ice Breaker Questions For Dating

6. Compare him to someone famous 

Say something like “You look just like Ashton Kutcher from No Strings Attached,” but make it accurate. Chances are 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, and this confidence sets the tone for more interesting topics to talk about with a boy. 

7. 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.

Related Reading: Best Netflix Series And Shows For Couples

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?” 
  • “Don’t you think Jenna Ortega was awesome in the series Wednesday?”
  • “Have you taken a look at the Top 10 shows on Netflix? I think it’s great that a lot of documentaries are making the cut!”

People love sharing pop-culture content that they enjoy, so he will definitely enjoy talking to you about such topics     . If he’s cute and passionately nerdy about shows and web series, he will most likely 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.

Netflix and chill
Send him memes to make his day

8. Use music to break the ice

A conversation starter such as “What are you listening to these days?” always helps break any initial awkwardness on social media or on Tinder and other dating apps. 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 online, you can ask him about his music preferences or about his favorite artists.

9. Talk about his pets

If you see a guy posting photos with his pets on social media or on apps for online dating, the easiest way to get to know him better is to talk about his furry friends. If he is a pet parent, it’s safe to assume he likes animals. So, 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.

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

10. 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.

How To Start A Conversation With A Guy In Person

A lot has been said about scoring guys on social media. But what happened to the old-school way of getting to know a guy in a face-to-face situation? Do you often wonder how to start a conversation with a guy in person? Here are some tips to consider to start a conversation when you meet someone special for the first time or bump into a guy you fancy:

1. Start simple and straightforward

Start with something simple and fresh, even if you are discussing something as mundane as the weather. Here are some examples:

  • “I only love rainy days when I’m indoors. Are you enjoying the weather today?”     
  • “Can you believe how hot it was in Seattle yesterday?”     
  • “Do you think the skies might clear soon? I have a trip planned for this weekend that I don’t want to cancel.”

These conversation starters can lead to a longer exchange. This is a simple and effective answer to “how to start a conversation with a guy?” These remarks don’t command immediate interest but will guarantee a response that you can build upon. And if he shows you interest, it’s a good sign that you should continue the conversation.

2. Try some tattoo talk

When people get tattoos, they often have an interesting story and reason for getting them. So, the guy you fancy in your French class has a visible tattoo! Well, all you have to do is ask him about it. He would love to tell you his backstory if you show some 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. Check if he’s making eye contact, and match his vibe.

Related Reading: 20 Simple Ways To Make A Guy Miss You

3. Bring up current events 

So, you like the nerdy coworker and want to make friends with him? Start with discussing current affairs. But don’t go too deep because you don’t know how interested or well-versed someone might be in these things (unless you’re confident you too are equally well-acquainted with such topics). When something is 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.

4. Go old school 

One way to charm a guy in a face-to-face conversation is to simply introduce 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 over you in no time. Take him out to a coffee shop. Relax and have a soothing conversation. Make eye contact to let him know you like him. Remember, positive body language goes a long way into making a guy talk.

Related Reading: Expert-Backed Signs Of Male Body Language Attraction

5. Offer help or ask for it

When a guy says “hi” every time he sees you, and you like him too, offering help when you see him struggling is a good idea. And the guy is almost sure to respond to you. If you’re still wondering, “Being a girl, should I reach out to him first?” Hell, yes, you should! Here are some examples of what you can say to a guy at work you’ve been trying to start a conversation with:

  • “I think you could use some help with those cartons”      
  • “Do you need me to bring out the other files for you?” 
  • “Hey! Looks like you’re new here and a little lost! The cafeteria is on the other side, if you want some hot coffee.”

While you’re helping him, go ahead and flirt just a little bit. And it’s needless to say that guys usually don’t say “no” to girls who ask for help. Make the first move and ask him for a small favor.

Offer help or ask for it
Discuss your common friend

6. Use your surroundings

Striking up a 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. If you’re at a coffee shop, talk about how you like your coffee. 

Keep it simple and slowly rope him into the conversation. This way, there will be no dearth of things to talk about with a boy. But remember to read his eye contact and pay close attention to his body language in social interactions, as that will help you connect with him.

7. At a party, ask him what’s ‘his poison’

When you want to approach a guy at a social gathering or a party, you can go over and ask him what’s in his glass. Try saying something like “Looks fancy, what are you drinking?” If you’re lucky, he will let you try his drink and maybe even ask if you want the same one. Just be a bit confident, and half the game is won!

Related Reading: How To Flirt With A Guy At Work?

8. Guess his type

If you’re approaching him directly for the very first time, you can try this subtle and flirty trick. Just comment on what you think he does or what vibe he is giving off. If you think he is the quiet type, say something like “You seem like a writer to me. Are you into poetry?” Even if he is the total opposite of what you’ve guessed, the fact that you approached him will still impress him.

9. At a library, ask what he’s currently reading

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. Try saying something like “Oh I’ve read that book. You should totally try it!” Or you can also look at the book he’s picked up and give him your opinion on it

Related Reading: 21 Best Relationship Books That Everyone Should Read

10. Discuss a mutual 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 or share an inside joke that you usually share with your friend. That might open up a treasure trove of stories that you two may start discussing. In fact, this is a sure-fire way to begin small talk with guys in social situations.

How To Start A Conversation With A Guy On Text

There’s nothing like texting when it comes to striking up a good conversation. While hitting on a guy on a modern dating app or approaching him at a party may be too obvious, texting is a subtle way of letting someone know you wish to know them better. So, here are a few tips on how to how to start a conversation with a guy on text:

1. 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. It could be a photo of your dog or of some place you’ve been to. That is sure to start an exchange of pictures and a cute conversation for you to get healthy flirting cues from.

Related Reading: Types Of Guys Women Want And Don’t Want To Date

2. Rely on those GIFs 

GIFs are hilarious and can convey messages wonderfully if you use the right one. They’re amazing icebreakers and usually incite positive responses from a guy if he’s genuinely interested. Don’t end up getting confused because of the sheer number of GIFs available. 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 GIF, and you’re bound to get him laughing. If he replies with another GIF, start texting him.

3. Compliment him 

Ego-boosting texts do wonders! React to his WhatsApp display picture with a compliment and make him feel special. Here are some examples of what you can text as conversation starters, though they are basic compliments: 

  • “That shirt really brings out the color of your eyes” 
  • “Your new haircut looks fab!”
  • “That pair of glares sure looks classy! You have good taste!”

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 and that you have shown genuine interest.

Related Reading: 15 Compliments For A Man’s Smile To Make Him Smile More

4. 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. So, how to tell a man he’s hot? Get to know him a little before you really start to come on strong. While some sexual innuendo can really spice it up, too much of it will do just the opposite. Sexual hints at the very beginning of a conversation could turn him off or make him unnecessarily aggressive. Be careful about how far you go when you’re flirting with a guy. Don’t give in too easily. Instead, make a man want you.

5. Share an interesting anecdote

Wondering how to leave him wanting more over text? Well, to keep him hooked onto your texts, you can bring up an interesting anecdote. It could be something from your childhood or even something you just experienced the day before. Saying something like “I have to tell you the craziest story” works in such cases. Not only will you be able to start a conversation with a guy, but if your story is amusing, you’re probably going to make him laugh too. And trust us, this will be a great start!

Related Reading: 35 Best Conversation Topics If You Are In A Long-Distance Relationship

6. Keep it casual 

Do you often say to yourself, “I really like this guy but we barely even talk”? Wondering how to get him to open up over text? Well, give it time. When you start texting a guy, try to steer clear of asking questions that he may not be comfortable with. You don’t want to touch a raw nerve or make him conscious of his insecurities. Keep it simple, fun, and not too serious. Don’t straight up ask him about his problems or struggles. There is a different time and place for controversial relationship questions. Be a good listener and hear him out.

art of woowing

7. Play up your common interests 

If you’re wondering how to text a guy you’ve never talked to but know that you two have a shared love for something, start there. Any common interest is a good excuse to text your crush. Find out what you both like and get talking.

“Hey, I saw on your WhatsApp status 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 ground. If you don’t happen to come across a status or photo that suggests a commonality, you can always ask him what his hobbies are and try to see if you two have anything in common.    

Related Reading: How Important Are Common Interests In Relationships?

8. Don’t reply with one-word answers

So, how to text a guy you just met and keep the conversation going? “Oh, fun!”, or “Nice to hear” are responses that you may not always get a quick reply to when you’re texting a guy you like. Your response should always have a bait for a follow-up conversation or a new topic. While short and sweet is the way to go, texts that are 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 open-ended questions such as “What about you?” Here are some examples:       

  • “Yeah, I like to read. What about you?” 
  • “I see you love traveling. But do you think over-tourism is a rising concern?”
  • “Wow! You seem to be a foodie. Did you try that new Chinese restaurant two blocks away?”

When you start a conversation with a guy over text, it’s important to keep him engaged this way. This will also help you end the chat on a high note.

9. Text him about sports

Since Americans are largely passionate about sports, it’s hard to find someone who’s totally indifferent to it. Text the guy something like “Did you watch the Lakers play last night?” or ask him which sports team he supports. This is a sure-fire way you can get him pumped up and talking about his team.  

Related Reading: 51 Impressive Second Date Ideas

10. Add variety

Don’t linger on one topic for far too long when you’re texting a guy, and keep an eye out for when the spark is fizzling out. If the conversation is losing momentum, hop on to another topic or ask him a new question. A conversation can quickly turn monotonous if you don’t keep working on it. Moreover, your attempt to talk to him may just turn into one of those flirting signs guys miss if he is not invested in the moment. Add variety to keep your love interest hooked!

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 meme, or even flirting with him
  • Find a common ground and talk about it, show an interest in what he’s saying, and steer the conversation toward interesting topics 
  • Don’t overthink it. All you have to do is shoot your shot!

So, hope we helped you with enough examples of conversations to have with a guy you like. Starting a conversation with a guy is really no rocket science. Guys are just as human as us girls. All you need to do is take a deep breath, 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. But most importantly, 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.” Starting a conversation with a guy isn’t that hard. All you’ve got to do is be confident. Once you begin, take the help of open-ended questions to keep him engaged in the conversation.

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. Likewise, you can comment on his photos or send him a funny meme. Once you get started, you’ll have no dearth of things to talk about with a guy.

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