How to Start a Conversation with a Guy: 25 Subtle Moves That Work

Knowing how to start a conversation with a guy can be intimidating at first, but they’re only human. Read this to know how to talk to a guy confidently.

We always expect men to be the ones to approach us. Have you ever approached someone of the opposite sex? Knowing how to start a conversation with a guy can be overwhelming, but it gets easier when you know how.

However, you shouldn’t expect guys to make the first move all the time. After all, what happens when you deal with someone shy and awkward? A conversation with them will never happen if you wait for them to approach you.

We’re well into the 20s and it’s perfectly okay to approach a guy first! Especially if you have the confidence and charm to do so, why not? He might even find it attractive that you didn’t hesitate to approach him first.

[Read: How to approach a guy you’re into and remain calm and cool all the way]

Why should you start the conversation first?

There are several reasons why you should initiate the conversation first. One of the reasons why you should learn how to start a conversation with a guy is because you’re literally one conversation away from a potential date or even a relationship. Even if a guy is too shy or awkward to approach you, or whetever else the reason may be, why ruin a perfectly good opportunity waiting for him to pluck his courage.

All great relationships start with a simple approach! You never know, it could be what your crush is waiting for before asking you out on a date. Secondly, it eliminates the missed opportunity of dealing with awkward and shy guys. Really, you’d be doing them a favor by initiating the conversation.

Lastly, it gets all the anxiety and fears out of the way. You’ll never get anywhere with your fear of rejection or fear they don’t like you back. How will you know the answers to these if you don’t start the conversation, right? [Read: 15 subtle but very effective ways to encourage a guy to make the first move on you]

How to start a conversation with a guy

Okay, we get it, you’re scared of rejection *you’re not alone there!*. However, the fear of rejection won’t get you anywhere in your dating life. If anything, this fear is holding you back from going out on such great dates! Learning how to start a conversation with a guy won’t give you a bad reputation for being straightforward.

In fact, it eliminates that pressure off guys by talking to them first. Don’t know how to start the conversation? Don’t worry, we have some tricks up our sleeve for you to try out!

In this feature, we’ll guide you through everything you need to know on how to start a conversation with a guy. [Read: How to start a conversation with a stranger & say the right things]

1. It’s all in the eyes

Sometimes, guys just need a sign that you’re interested. It doesn’t have to be anything intense, but it can be as simple as eye contact with a smile. This is the most subtle way on how to start a conversation with a guy.

If he notices that you’re engaging in eye contact, it gives him a sign you’re interested in a conversation with him. If he looks back, that’s your cue! It’s the easiest way to start a conversation with him, without making the initial approach. [Read: The all-in-one woman’s guide to making eye contact with men]

2. Classic accidental bump

This is another subtle move on how to start a conversation with a guy without being too obvious. Perhaps you could “accidentally” bump into his shoulder while walking or in a bar, bump into a guy while you’re about to get drinks.

Of course, you say sorry and smile, giving him an opportunity to comment something back if he’s interested too. It completely avoids you having to think of a witty conversation starter. You never know, it might be effective enough to turn into a full conversation, landing you a date invitation! [Read: Do guys like it when women make the first move on them?]

3. Ask for help

Got lost? Sure, you live the next block over, but you’re not very familiar with the area *at least, that’s what you want him to think.* Guys like feeling needed so asking for help is the perfect way to initiate a conversation with them.

If you’re at loss for the perfect conversation starter, you can pretend like you need help with something. So, he may actually walk you to where you need to be or show you on the map. If he walks you to your destination, this is your chance to converse with him! [Read: Damsel in distress – Why men find them so irresistible]

4. Don’t I know you from somewhere?

Ah yes, the classic “you look so familiar” line. This is a great way to start a conversation as you two spend minutes listing and naming off people and places that you go to.

Whether you’re just pretending to know him from somewhere or not, it still works enough to initiate a conversation. [Read: 15 easy conversation starters with a guy you like]

5. Have the time?

This one works well enough if you use your creativity to your advantage. You also have to think fast when he responds with the time otherwise, it’s going to end in an awkward silence.

You wouldn’t want your first conversation to end in disaster, right? Make sure you’re not wearing a watch or have your phone glued to your hand before trying this one out.

6. Work off your mutual friends

Do you actually recognize him? Is he a friend of a friend? Then why not start the conversation by asking him this. You don’t even have to be as nervous talking to him since he’s not practically a stranger to you.

This is an incentive to talk to him, more because if you share the same vibe, your mutual friend might invite him to more hangouts and parties! [Read: 20 signs he just wants to be friends even if you’re hoping for more]

7. Technological fail

Okay, let’s admit this sexist possibility of truth, women aren’t exactly known for being the best at fixing technological problems. Whether it’s something simple as your phone not working or your laptop misfunctioning, don’t hesitate to ask for help!

Most likely, he says yes and there you go, the ice has been broken. You can now talk about whatever you want at the back of your mind!

8. Social media is your friend

Social media is the easiest method if you want to try to start a conversation with someone. Honestly, if you want to learn how to start a conversation with a guy, social media is your very best friend and saving grace! If they post a picture, tweet something, or upload a story on their Instagram, you can easily comment!

This is a great way to start a conversation as it skips all the awkward and scary parts of an actual conversation. [Read: How to talk to your crush – The secrets to make them fall for you]

Want something more subtle? If this guy you like comments on any mutual friend’s post or even if you come across a random post he’s commented on, just reply to his comment. It’s subtle, it’s slow, but it will get his attention.

9. Is this seat taken?

You can be in class, on the bus, at the doctor’s office—ask him if the seat beside him is taken. It’s a very subtle yet effective way on how to start a conversation with a guy. Once you’re seated beside each other, you can talk about anything under the sun!

Just make sure to not share an awkward silence together. Go on, just talk about whatever and you’ll find that the rest will follow. [Read: How to make small talk without feeling awkward]

10. Must love dogs

You cannot fail at having a conversation about someone’s dog. This works for everyone. This is the entire logic behind why when you walk your own dog, a lot of strangers approach you because of how eye-catching your dog is!

If you see a guy walking his dog, don’t feel shy to stop and ask to pet it. This gives you an opportunity to start a conversation and develop a connection with him! You don’t even have to limit your conversation with dogs alone – it can be anything!

11. Ask about the music

If you’re at a coffee shop or bar, easily start a conversation about the song that’s currently playing. It’s a pretty safe way of starting a conversation.

Really, he’s not going to ignore your question. Also, everyone loves music so it’s an interesting starting topic to begin the conversation with. [Read: 20 very easy conversation starters you can use on a guy you bump into]

12. What’s he reading?

If you’re fond of books, this is a great line to use in bookshops and coffee shops! If you’ve always had the secret dream of potentially landing a date because of books, it’s your chance to use this line. Maybe he’s on the bus or at the airport and he’s just hanging out, reading a book.

Wait for him to look up and then ask him what book he’s reading. If he’s halfway through the book, you can even ask him what he thinks about the book so far and you can discuss your thoughts about it. [Read: 20 signs of attraction in the first conversation]

13. What’s the score?

If you’re at a pub and the game’s on, ask him what the score is. Make sure it’s a sport you’re semi-interested in or else you may have to sit with him and bear his rambling about offense and defense.

Guys can talk about games and sports forever, so make sure it’s something you have in common! Otherwise, you might bore yourself to death.

14. Dance!

This is only if you’re at a club or house party. You can dance next to him or grab his hands playfully. This is actually a pretty common way on how to start a conversation with a guy.

You get to have fun and show your playful side at the same time *while also showing off your dancing skills!*. You should ask him his name afterward and he might buy you a drink, if he likes where the conversation is headed. [Read: 25 subtle moves to start a conversation with any guy you want to talk to]

15. Compliment him

This may sound weird to you, but don’t be shy to let him know that you like his shirt or his hair. In fact, compliments work wonders in starting a conversation, even for a stranger!

Since guys barely get any compliments regularly, giving him one would definitely grab his attention. Everyone likes to be complimented, so why not use that as a way to talk to him. [Read: 30 unique compliments for guys that will absolutely make his day]

16. Airport chatter

Wondering how to start a conversation with a guy when you’re traveling? If you’re on a train, bus, or plane, just ask him where he’s going. This is one of the most common ways on how to start a conversation with a guy when traveling.

You never know, you could be travel buddies or develop into something more! You two can exchange travel stories and maybe even contact information, right?

17. You look like…

Playing the “you look like this celebrity” isn’t a bad way to start a conversation. You just need to make sure that the celebrity is attractive.

It could even pass off as a compliment that’ll flatter him completely. Of course, don’t go overboard and say he looks like Brad Pitt when clearly he doesn’t. [Read: Clever ways to get a guy’s attention in any circumstance]

18. The weather

Are you sweating from the heatwave that just hit your town? I know it sounds lame, but the weather is a great excuse to talk to someone. Even if this is probably the lamest starter you can think of, it’s an effective way to grab a guy’s attention and just start talking.

Especially when the weather’s particularly intense, he won’t even notice that you’re just trying to start a conversation with him.

19. Tattoo

If he has an interesting tattoo and it’s visible, well, why not ask him about it? Usually, people have a story behind their tattoos, so it’s a great way on how to start a conversation with a guy.

After he reveals the story behind his tattoo, you can use that as a stepping stone for other topics. Plus, it gives you a reason to stare at him without looking creepy. [Read: Just being me: 15 unexpected things guys like about girls]

20. Send him a drink

Okay, if you do this, you’re a real girl boss, and we applaud you. If you’re at a restaurant or bar and you have glanced at each other, send him a drink. Again, we’re living in the modern dating culture and there’s no shame in buying a guy a drink!

At least, he’ll know you’re interested and maybe, just maybe, he’s interested in you too! [Read: How to make the first move on a guy – 15 really creative but sweet ways]

21. Open with a joke

Jokes will never go out of style, especially when trying to learn how to start a conversation with a guy. The best way to start a connection without making things awkward is by making them laugh.

Whether it’s a pick-up line or sarcasm, just use anything to your advantage in making them laugh! This is probably one of the most effective ways in starting a conversation. [Read: How to make someone laugh when they’re down & lighten their burden]

22. Working on anything exciting lately?

This is the perfect conversation starter when learning how to start a conversation with a guy. Especially when you’re in an office event or you’re around corporate individuals, it’s a great line to use.

This question is basically an alternative to asking what they do for a living. People love talking about what excites them, so it’s perfect to use when talking to a guy!

23. Having fun?

If you’ve ever been alone at a party, then someone must’ve already used this line on you. If you notice a cute guy alone at an event or party, it’s a great question that can break the ice.

It’s a much better question than asking them how they are. Frankly, how do you answer the question, “how are you?” [Read: Life of the party – How to be noticed and loved by everyone]

24. What’s your story?

Okay, we know this seems like an intimidating conversation starter, but it works! This is best used in a bar setting. So, the next time you see a guy drinking alone in a bar, feel free to ask him what his story is.

It’s not just an effective way on how to start a conversation with a guy, but an interesting one. It’s a question that’s filled with meaning and substance.

25. This is my first time here

There’s nothing more inviting than being a lost girl *remember how guys love to help and be the hero?*. By asking this question, you’re letting him guide you around a new place, event, or whatever new situation you’re in.

[Read: Drawing a blank? Try these 25 good conversation starters!]

So, what are the easiest ways to start a conversation with a guy?

Being approachable and friendly is always the best way to start a conversation. Of course, you can’t build a connection if you seem intimidating and stiff.

Ease up and don’t hesitate to joke around when you first talk to him. After all, everyone likes a sense of humor *including that cute guy you like!*

[Read: 13 very charming ways that’ll instantly make you way more approachable to guys]

Now that you know how to start a conversation with a guy, you’re going to have to give these methods a try. Don’t be nervous – go on and try them out!