How to Start a Conversation With a Guy: 30 Charming Ways

Whether in person or over text, it can be intimidating to be the one who initiates conversation with a guy. If you are unsure how to start a conversation with a guy you’re interested in, know you’re not alone. 

It can be challenging to determine the best way to approach a guy and strike up a conversation that will hopefully lead to something more. 

How to start a conversation with a guy?

Perhaps you’ve had your eyes on someone at the gym or a coffee shop you frequent, but you’re stuck pondering how do I talk to him. Or maybe you’ve already exchanged numbers, and you’re stumped trying to come up with an interesting opening line.

This article will explore practical tips on talking to guys in any setting.

Related Reading : What to Look For in a Guy: 35 Good Qualities in a Man

30 best ways to start a conversation with a guy

Let’s jump into the best ways to start a conversation with a guy and form a connection.

1. Simply introduce yourself

Your opening line does not have to be anything fancy or elaborate. Sometimes the best thing is not to overthink it. Please take a deep breath, walk over, smile, offer your name and ask for his. 

If you’re unsure how to start a conversation with a guy because you don’t know anything about him, a simple introduction could be the way to go.

Related Reading: What is Flirting? 7 Signs Someone is Into You

2. Use the setting as a conversation starter

Try commenting on a shared environment that you find yourself in. This could look like pointing out the unique ambiance at the coffee shop or how packed it is at the gym. This can easily lead to further conversations! 

And for some reason, if you don’t receive a response, you can always play it off like you were talking to yourself.

Also Try: Platonic Or Romantic Love Quiz

3. A remark about the weather

While this may not be the most thrilling conversation starter, the goal is to make initial contact- and from there, you can branch out into more fascinating topics. Simple statements like “It’s such a nice day today” or “Did you see the snow this morning?” can be enough to get the ball rolling.

4. Offer a genuine compliment

Tell him how much you love his colorful shoes or the stickers on his laptop. Or if he’s a co-worker, note what a great job he did on a recent presentation. 

That being said, it’s important to be thoughtful about what compliments you give. The key is ensuring your compliment comes off as authentic and unforced.

5. Comment on something he’s wearing

When considering how to start a conversation with a guy, an important strategy is to be observant and pay close attention. Ask him about the band on his t-shirt, or whether he went to the school displayed on his hat. 

6. Ask about his tattoo(s)

If the guy you’re interested in has noticeable tattoos, ask what they mean to him. This gets the conversation started and can give you more insight into who he is as a person.

7. Pose a question about his hobbies or interests

It can be difficult to start a conversation with a guy if you don’t know his interests, but you must start somewhere! 

This is also where commenting on the environment can work to your advantage. Say you’re at a concert; you could ask, ‘Do you go to shows often?’ or ‘Have you seen this band before?’

Related Reading : How Important Are Common Interests in a Relationship?

8. Start with the pup

A dog is a low-pressure way to talk to guys! Upon running into a cute guy walking his dog in a local park or your neighborhood, ask if you can pet his pup. 

From there, the conversation may unfold into a discussion of the dog’s name and breed, and you can also inquire about his favorite local parks or hikes.

9. Have a mutual friend make an introduction

Perhaps you are at a party when you spot a guy that intrigues you from across the room. Ask him how he knows the host, or see if your friend could make the introduction.

10. Ask him for a favor

If you’re looking for a subtle idea for how to start a conversation with a guy, ask him to assist you with something. People love to feel helpful and needed. 

Go up to him and ask if you could borrow a pen if he could help you open something or teach you how to use a machine at the gym.

Related Reading: Romantic Love Messages for Your Partner

11. Request his advice or recommendations

Ask him if he knows a spot for good Thai food in the area. If you know he’s a writer, see if he has any tips for increasing motivation and boosting creativity.

According to relationship coach Christiana Njoku,

Seeking his recommendations has a way of making him feel heard and valued. For example, “Learning new skills is like leveling up in life! I’m looking for a great academy to learn some new life skills—do you have any recommendations or experiences you’d like to share?”

12. Prompt him for his thoughts

See if he’s ever watched a TV show or movie you’re considering checking out. Or inquire what he thinks of the book he’s carrying with him. This not only ignites conversation but shows that you value what he thinks.

Let’s also look at some strategies for how to start a conversation with a guy over text.

13. ‘Thinking of you’

Simple and direct, this is a sweet way to let your crush know he’s on your mind. It can be easy to get caught up trying to craft the perfect opening line. Sometimes, it’s best not to overthink it. A short and sweet message like this demonstrates thoughtfulness and interest.

14. Reference a common interest

Tap into previous interactions you’ve had when considering how to start a conversation with a guy. If you know you both watch a TV show, ask him if he’s seen the latest episode yet. If you follow the same sports team, you could say, ‘The game last night was wild!’

15. Offer a compliment

Christiana Njoku has this to say,

Positive affirmations and compliments are good conversation starters. Learn how to start a conversation with a guy by simply giving him a compliment.

It can be more challenging to come up with a compliment when not sharing the same physical space. 

However, if you noticed an awesome photo he posted on social media, compliment him on his photography skills. Or maybe you’ve picked up on his characteristics from your interactions thus far and can point out, ‘I admire how hardworking and driven you are.’

Related Reading  : How to Compliment a Guy- 100+ Best Compliments for Guys

Watch this video to learn how to compliment a guy:

16. Send a funny video or meme

A recent study revealed that humor is one of the top three most desired traits in a partner. Sending a silly video or meme can be a great way to break the ice and start things off with a laugh.

17. Share a joke

Along the same lines, send a cute knock-knock joke you’ve heard or even look one up online. It’s okay if it’s a little cheesy! He’ll have to reply to get the punchline.

18. Create suspense

Send something like, ‘The craziest thing happened this morning. Remind me to tell you about it later!’ or ‘I thought of the funniest story; you’ll crack up when you hear it.’ He will be on the edge of his seat to find out more!

Related Reading: Is He into Me? How to Tell If a Guy Likes You

19. Send a relevant photo

Say you’re checking out that great donut place he recommended, or you see something that reminds you of him. Sending that with a short caption can be a conversation starter that feels authentic and unforced.

20. Ask him for recommendations

It can be simple, like ‘I’m craving a good croissant, where should I go?’ or ‘Have you read any good books lately?’

21. Let emojis do the talking

If you’re stuck on how to start talking to a guy, stop worrying about finding the right words. Instead, send over a row of emojis describing your day or mood to see if he can decode your message.

22. Get your flirt on

On days you’re feeling particularly bold, send something direct like ‘I can’t get you off my mind.’ This demonstrates clear interest and confidence and can escalate your connection to a new level.

Also Try: Quiz: Do His Texts Mean That He Likes Me?

23. Pose a thoughtful question

It’s easy to overthink how to start a conversation with a guy. It’s important to remember that what we say is less important than displaying genuine interest. Asking something like ‘how was your weekend?’ or ‘How did work go today?’ can be all you need.

24. Follow-up

Perhaps your crush shared with you that he had a big deadline coming up or was doing some traveling. Strike up a text conversation by asking how everything went or what he did on his trip. 

25. Show interest in learning about him

Whether it’s asking him more about his job or hobbies, prompting him to share more about himself shows that you are invested in making a meaningful connection. 

It is scientifically proven that people love to talk about themselves; therefore, giving them the space to do so can go a long way in building a bond.

26. Suggest a game of twenty questions

Initiating a game of twenty questions can alleviate the pressure of figuring out how to talk to a guy. It provides a built-in structure for learning more about each other and can be a way to move past the small talk and go deeper.

Perhaps you are worried about your rapport with your love interest getting trapped in cyberspace. Let’s end by exploring how to start a conversation with a guy in a way that can move your interaction into the real-life realm.

27. Reference a current task

Toss out an SOS- ‘I need a study break; meet me at the coffee shop?’ This offers a low-key opportunity to see each other in person while keeping it lighthearted and casual.

28. Gauge his interest in a certain activity

You might send something like, ‘I want to play mini golf, but my friends aren’t into it. Would you want to go?’ Proposing a specific activity or event offers the chance to spend time together and get to know each other better without the pressure and formality of asking him on a date.

Kick-starting a conversation with a guy should be strategic – it’s all about timing! Something like “I see you’re a football fan; which club do you support and why?”.

adds Christiana Njoku

29. Get his opinion

Ask if he’s ever tried a certain restaurant or ice cream spot. Whether he says, ‘Yeah, it’s the best!’ or ‘I haven’t but it looks good,’ there’s your in to suggest checking it out together sometime.

30. Leave him wanting more

If you’re wondering how to start a conversation with a guy that will keep him intrigued, send a message telling him that you have the funniest thing to tell him. Suggest meeting up for a walk or coffee sometime soon so you can relay the story in person.

Some commonly asked questions

It can be intimidating to know how to start a conversation with a guy over text, especially if you want to steer away from the generic ‘Hi, what’s up?’ or ‘How are you?’

Please keep reading for more suggestions on how to send him a message that stands out. 

• What should I text a guy first?

Some simple ways to spark conversation are:

• • Referencing a common interest like a movie series you both love or a musical artist you mutually follow
  • Sending a picture of something relevant to past discussions you’ve had
  • Opening with a funny video, meme, or joke
  • Sharing an anecdote of something that happened to you that day
  • Asking if he might be interested in joining you for a specific activity/event
  • Posing a thoughtful question like ‘What did you do over the weekend?’ or ‘What projects have you been working on recently?’

• Do I text him first or wait?

If you’re interested in progressing your connection with your crush, there’s no need to wait for him to reach out! 

A recent study on attitudes around modern dating shows that most men appreciate when a woman demonstrates interest. 94% of men would like it if a woman reached out first following a successful first date.

Given the research, being the one to initiate a text conversation just might brighten his day. Reaching out first clearly demonstrates that you’re interested in pursuing the connection further; you’re confident and not one to play games. 

Final takeaway 

Throughout this article, we have discussed how to start a conversation with a guy by either initiating interaction in person or through text. It can be intimidating to make the first move; however, it can be a relief for many people on the receiving end. 

Instead of arbitrarily ‘waiting a certain amount of time,’ you can decide to demonstrate confidence and genuine interest by opening the avenue for connection.

If you believe you may benefit from further guidance surrounding building or maintaining healthy relationships, consider seeking individual or couples counseling support. Working with a trained professional can help you move closer to the relationships you want in your life.

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Noah Williams Author

Noah loves to write on matters of the heart and mind. His experiences have taught him that being an honest friend who communicates well and giving importance to self-love can go a long way in maintaining loving relationships. When... Read more he’s not writing or advising people on how to thrive in their relationships, he loves exploring new places with his partner, working out, and pretending that he’s good at cooking exotic stuff. Read less