Making the first move to approach a guy can be terrifying, so much so that you may just sit, make and watch him from the corner of your eye for weeks before you even consider going up to him. And maybe when you finally make the bold decision to go up to him, you're at a loss of what exactly to say. With these simple tips, you'll learn how to start a conversation with a guy with confidence and ease.

How to Start a Conversation with a Man


Ask him for help

When you see your guy approaching, causally ask for his help with anything. If your hands are full, accidentally drop your keys or a pen and ask him to get it for you. You'll want to plan this approach out ahead of time, but if all goes well, he'll stick around for a short conversation with you.


Ask to sit next to him

One the train, in the work break room, library...wherever it may be, just give him a warm and welcoming smile and ask if it would be alright to sit next to him. Chances are you'll draw him in with your smile and he'll start up a conversation with you!


Get a little close

If you just so happen to be in waiting in the same place as him, either for the train or bus or in a line, use this trick. Accidentally brush up against him as you go to look at something or pick something up. When he turns around, give him your warmest smile and apologize. You put the ball in his court and most often he'll start talking to you as you both wait.


Borrow a pen

Pull out your calendar or notepad and pretend like you are looking for something to write with. Move a little closer to him and finally ask him if you can borrow a pen. Take it graciously and write any quick note down and return the pen. Smile and thank him, or tell him he's a lifesaver. Most times he will then use this as a chance to talk to you if he's interested.


What time is it?

If the guy you've been watching for a while wears a watch, you have the perfect opportunity to start a conversation with him. Nonchalantly ask him what time it is. Once he has responded, be sure to give him a compliment on his watch. When using this simple conversation starter, just be sure to have your cell phone hidden away, otherwise he might just think you're odd for not checking the time on your phone instead.


Just say “HI”

Too shy to actually try and have a long conversation with the guy you've been eyeing up? Instead of stressing over how to start a conversation with a guy, simply smile and say “Hi” the next time you walk pass him. Just keep walking in the direction you are going, don't look back and don't pass or hesitate. The next time you happen to walk pass him again, read his body language. If he's smiling, he might be interested in you and may start the conversation this time.


Talk about the weather

It may seem cliché, but the weather can be the easiest way to get a conversation started. It's best to use this when it's fairly nice outside. Once you made a comment about what a lovely day it is, he will take this opportunity to comment, make and talk more with you if he's interested.


Compliment him

If it's a guy you see on a regular basis or he is just wearing something you think looks great, tell him. Be sincere and specific when giving him a compliment about his attire. Try to follow the complement up with a question. He'll then take the lead to try and get you to keep talking with him.


What's he reading?

If you see him constantly with a book in his hand, this can be an ideal opportunity to start up a conversation. You don't want to interrupt him, so wait until he looks up and you can make eye contact with him when you can smile and ask him what he's reading. If it's an author you are familiar with, you might want to mention a book you've read by the same author or simply ask if it's any good. This can get him talking a great deal if it is interested in you as well.


Talk sports

If you happen to be sitting at a bar or local pub close to someone you think is attractive, casually ask him about who he thinks will win or the rules of the game he just saw. Most guys love to talk about sports, so this can be a good way to start a conversation without any of the awkwardness.


Get directions

Even if you know where the place might be, the best way to strike up a conversation is to ask him for direction. Most often he'll love telling you the best way to get there and if he's really interested and headed in that direction, he might even offer to show you the way. How to start a conversation with a guy can begin in this least expecting way and can end up as an impromptu hang out or number exchange.


Ask about the weekend

It might take a little more courage to use this conversation starter, but if you regularly see the guy and you happen to be sitting or standing close to him, smile and ask how his weekend was. If the weekend is approaching, then smile and ask if he has any plans. This is one trick that might even lead to him asking if you want to make plans together one weekend.


His celebrity lookalike

Not only will this break the ice and get the conversation going, it can be an easy way to pay him a compliment. If he looks like a hot celebrity, let him know you think so or ask him if he's ever been compared to so before. You don't want to stretch this one too far but it can be effective as starter.


You look familiar?

This is often a common way to start a conversation with anyone. Simply tell him he looks familiar and if you guys may have run into each other before. This conversation starter almost always works and you never come off looking like you are trying to hard.


Mutual friend

If you know you both have a mutual friend or even a co-worker, use this as a way to get the conversation going. You can keep talking with asking if he happened to hang out with them recently.


Look for tattoos

If he has a tattoo, then you can easily use this to start a conversation. Most people have no qualms about showing off their ink work, so just take notice of any visible tattoos and complement it or ask for the meaning behind it. Every tattoo has a story, so this is a highly successful way to get him talking.


Be funny

How to start a conversation with a guy? Make him laugh and intrigued. Men will instantly take notice of a woman with a sense of humor, so whenever you get the opportunity, make him laugh. This doesn't have to be anything that takes carefully planning, just a simple joke with suffice. 


Be bold

If you have the confidence and know you both have been eye flirting back and forth, then just go up to him. Introduce yourself and the rest of the conversation will surely follow.


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