How to Start a Conversation With the Guy You Like

By on June 10, 2014

You’ve had your eye on this guy for quite some time now. He sits across from you in class, he works in the same office, or you can’t keep your eyes off of him as he works the weights in the gym. Wherever he is, you want to talk to him, but you don’t know how to start. Here are some great ideas on how to start a conversation with the guy you like!


1. Eye Contact With a Flirty Smile

This is probably the easiest (and best) way to go about things. Not only does a simple, flirty smile let you know that they are interested in them, but 9 times out of 10 men like to make the first move. Letting him know you like him by using your eyes and a smile makes it easier and more comfortable for him to come on over and strike up a conversation. Plus you don’t have to do any of the work. Perfect idea for the shy girls out there!

2. Accidentally ‘Bump Into Him’

You’ve probably seen this one in the movies. The girl walks by and ‘accidentally’ knocks right into the man she is interested in. Her books fall to the floor, and suddenly they are both on the floor picking up the books and setting up a dinner date for that night. While it may not be that dramatic and you might not score a date right that second, you will at least be able to say one word to the guy- even if it is “Sorry!”


3. Ask Him For Help With Something

Men absolutely love to help. With everything. It’s simply in their nature to be the hero, and they will almost never turn down a chance to help a woman out. Whether you need help sharpening your pencil, opening up your water bottle, or even needing your car jumped- ask him! He will probably be more than willing to help you. Plus, when all is said and done, you can keep the conversation going with a simple “You’re so helpful” compliment. Another something that men absolutely love to hear from a gal.


4. Ask Him About Work/School

If you’re both in the same class, ask him what his major is or what he thinks about the class you are both in. If you work at the same place, ask him how he likes the work or if he has other goals in life. This not only makes it easy to start a conversation on something you are both involved in, but also makes it easy for a more in-depth conversation to arise. Just think about it. You could start off talking about how terrible he thinks the class is, and suddenly the two of you are talking about your future goals 20 minutes later. Endless possibilities with a very simple startup!


5. Compliment Him on Something

Man or woman, big or small- everyone loves to hear a compliment. So why wouldn’t this be an easy way to start a conversation with a guy you like? You don’t have to go in depth or come up with anything totally clever. You could simply tell him you like the color shirt he wore today or you think his new haircut looks great on him. Something as easy as that lets him know you like what you see, you might have an interest in him, and he can definitely talk to you whenever he wants. ‘Killing three birds with one stone’, or so they say!

6. Tell Him He Looks Familiar

Have you ever had someone walk up to you and say something along the lines of, “Wow, you look just like my aunt Joy!” or “Do I know you from somewhere? You look awfully familiar”. Whether they were just trying to be friendly or it was a guy trying to make a conversation with you, this is an easy trick that almost always works. Simply ask him if he might know you from somewhere else or if he had a different class with you. This will surely open up a long-lasting conversation without looking to obnoxiously obvious.


7. Ask Him For the Time

Don’t you love those easy questions that let you talk to someone without letting them know you’re too interested or giving yourself away easily? Yeah, this is definitely one of them. And even though everyone can easily grab their phones and check the time, it doesn’t mean we sometimes forget them, right? If you need a really quick way to strike up a conversation with a guy you’re interested him, just ask him for the time. He will tell you the time- and probably tease you a bit for not having your phone or forgetting to check there first. All that for just a quick little question- it’s simply brilliance!


8. Tell Him He Looks Like a Celebrity

This is like a compliment and an easy way to spark up a conversation in one. I mean, what guy doesn’t want to hear that they look like Channing Tatum or Brad Pitt? The options are really limitless when it comes to choosing the celebrity you want to compare him to, but we can almost guarantee he will enjoy this easy compliment. He might even want to hear your reasoning for the comparison- which, of course, means a longer conversation between the two of you. Huge win!!

9. Ask About a Mutual Friend/Coworker

So the two of you work in the same office, and you haven’t seen that one girl Chloe in awhile. She is usually always on time and never misses a day, and you couldn’t ever imagine a reason why she would be fired. So what gives? Even if you don’t necessarily care all too much where she’s been, it’s still a great way to start conversing with the guy you like. Ask him where a coworker has been, if he has seen them, or something along those lines. Whether he has or hasn’t, he WILL have to answer you. And who knows what will happen after that?


10. Ask Him If He Knows Him/Her

Let’s say you saw the guy you like hanging out with one of your good friends John. Viola! This is a GREAT conversation starter! Simply go up to him and ask him if he knows (insert name of person you know here). Say something like, “Hey, do you know John Smith? I thought I saw you two hanging out at the pub downtown last weekend”. Then go on to tell him how you know John and ask him about their friendship. Easy, right!?

11. Ask Him For His Name

You mean to tell me you still don’t know the name of that cutie that sits across from you in lab? Ok, even if you do- you shouldn’t let him know that. If you want to make it a bit obvious that you’re interested in him while still easing the way into a good convo, we recommend simply asking him what his name is. Trust us- he will love the easy attention and it’s a definite way for him to know that you’ve been checking him out and simply must know the name attached to that handsome face.


12. Tell Him He Did a Good Job on Something

Let’s say the guy you’re after just finished his oral report on the monkey species. You thought it was downright amazing and you can’t help but deem him one of the most (handsome) and intelligent men you’ve ever ran across. Why not tell him what a great job he’s done? This gives you a chance to compliment him, make him smile and feel manly, and also start a conversation. It could be anything from a nice dunk shot at basketball practice to an awesome job figuring out the hard math equation. If he did a great job, let him know! You can’t go wrong.


13. Ask Him If You Can Use His Phone

Ah, darn. Did you forget your phone at home again? Are you supposed to give your friend a call right when class is over to make sure she is there to pick you up? Well, you don’t want to be stranded, right? You really have only one option left available to you: go over to that cute guy and ask him if you can borrow his phone. Of course he will say yes, and the two of you can laugh about how hard it is to leave a phone at home. And if you’re lying and simply using this tactic to talk to him, make sure your phone is on silent so he doesn’t ‘catch’ you with a phone ringing in your pocket. I mean, how embarrassing would that be, right?


14. Start Small Talking Him

What better way to start talking to someone then by, well, talking to them? Small talk is obviously the easiest way to start talking to someone. Talk about how terribly hot it is out today. Talk about how mad you are that your favorite team lost last night. Talk about how you can’t wait for the weekend. Really, when it comes to small talk, anything goes. And don’t feel bad about it either. The only way to get to know someone is to start with the basics, and you never know where this simple small talk will lead.


15. Ask If You May Sit Next To Him

Even if there is a ton of seats available or none at all, give this a shot. Not only will you be able to sit next to him for the remainder of the event (and indulge in that masculine cologne he decided to wear that day) but you will also have an easy time making conversation with him. After all, he’s right next to you. You talk to someone who sits right next to you, right? It’s totally rude and awful not to do that, right? With this easy tactic, you are a show in for conversation.


16. Ask Him About a Feature, Such as a Tattoo

Want a unique way to strike up a conversation? Take notice of something that is different or unique about him, for instance a tattoo. Maybe you’ve noticed a tattoo of a little girl on his shoulder. Why not ask him what it is all about? You might find out he has a precious little 4 year old girl named Joan, or maybe you find out that is his little sister that passed away in a car crash. You never know until you ask, but you will have something to talk about nonetheless. Maybe you two will start sharing about other cool or special tattoos you have, and decide you’re a match made in tattooed Heaven?


17. Make a Small Joke

We can’t say this enough: men love it when a girl has a sense of humor and can make them laugh. So what better way to make a first impression than by telling him a silly joke? This will definitely intrigue him, and always give you two an easy way to keep talking. No awkwardness, to weird small talking. No quick questions, and no silly antics. Just a girl with a silly joke, making the man of her dreams laugh. Is there anything wrong with this picture? No, there isn’t. And if you have something funny to say, we definitely recommend relaying this funny message onto the guy you’re seeking. It’s simply one of the best ways to intrigue him!


18. Drop Something Near Him

Just like accidentally ‘bumping’ into him, this is one of the oldest tricks in the books- and probably another antic you’ve seen on television at one time or another. Whether you do the old ‘Oops, I dropped my pencil” right next to you or drop something else you will need right away, we simply can’t lie: it’s a great tactic and will definitely go places. He might pick up the pencil, look into your eyes, and suddenly realize that he hasn’t payed enough attention to you. Or he might just pick it up and hand it to you, continuing on with his day. We can’t guarantee anything, but you won’t know until you try, right? That’s like anything else!


19. Flirt With Him Casually

There is a huge difference between a casual compliment like the one listed above and a flirty compliment. If you really want to let him know right there and then that you are seriously interested in him, then try casually flirting with him. It doesn’t have to be anything outrageous like grabbing him by the arm, pulling him close, and telling him that you can’t stand another second without his lips attached to yours (although that might be the EXACT thought process going through your brain right now). Just come up with something simple. Unlike the casual, “I like the shirt you’re wearing today”, try something more romantic like, “Wow, I’ve never seen a man fill out a muscle tee like you do”, which could be proceeded by a bite of the lip or a touch of his arm. Either way, he will fall prey to your spell and you’ll be a shoe-in for future conversations.


20. Tease Him

When all else fails, why not revert back to our kindergarten days when showing someone you liked them was as easy as teasing them about their hair or chasing them around the playground. If you want an easy and cute way to start a convo with the guy you like, try a simple flirty tease. If he accidentally trips in front of you, giggle a bit and say “Ouch, nice one!” or if he does something wrong in class, smile and say “Way to go! Exit is that way!” something along those lines. Not only is it sure to get a smile, but he might tease a bit back- which can only lead to a little bit of conversation, and then who knows?


Tease him, flirt with him, ask him about the weather- there’s seriously tons of different ways to spark up a conversation with a guy you’re interested in. Nothing dramatic, and easy stuff even the shyest girl can do! What are you waiting for? Go get that guy!


What’s your favorite way to start a conversation with a man you like?

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