21 Ways to Start a Conversation with a Guy You like ...


21 Ways to Start a Conversation with a Guy You like ...
21 Ways to Start a Conversation with a Guy You like ...

You’ve seen him on the morning train every day for the past few months, and he’s so fine! Out of the corner of your eye, you think you’ve seen him looking at you, but you can’t tell for sure… the attraction is there, so how do you start an actual conversation? Here are my top 21 ways to start a conversation with a guy you’re interested in, along with a success percentage and how much courage you’ll need, on a scale of one (shy girls!) to ten (so bold!).

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Catch His Eye and Smile

Catch His Eye and Smile Level of Success: 60%
Level of Courage Needed: 6 of 10
The next time you see that guy, catch his eye and smile, maintaining eye contact for about three seconds before looking away. If at all possible, blush a little when you look away. I can almost guarantee that if the guy is interested too, he’ll smile back and probably even approach. If he doesn’t, make sure to catch his eye and smile one or two more times, each time a little longer. Toss your hair a little, and flirt like mad. Let HIM start the conversation!

Photo Credit: Alex Rozhenyuk


Ask to Borrow a Pen

Ask to Borrow a Pen Level of Success: 50%
Level of Courage Needed: 7 of 10
Bring a crossword or even just your agenda, day planner, or notepad. Rifle through your handbag, then get up the courage to smile brilliantly and ask him if he has a pencil or a pen. Chances are, he will, and will be more than happy to share with you. Use it to write a quick note or fill in a word, then put your notebook away and return the pen, thanking him gracefully. Say something like, “Thank you so much! You’re such a lifesaver!” If he’s interested, he’ll use this as a segue to begin a more meaningful conversation. If he just takes the pen back with a nonchalant, mumbled “No problem,” move on. He’s cute, but not at all clever.

Photo Credit: biffybeans

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Ask for the Time

Ask for the Time Level of Success: 50%
Level of Courage Needed: 7 of 10
If he’s one of those guys who still wears a wristwatch, or for some reason can pull off carrying a pocket-watch, ask him for the time. He’ll be delighted to show off his timepiece, and may even start the conversation then. If not, nudge him by thanking him for the time, and compliment his watch. That will give him another chance to start a conversation with you. Subtle but effective — just don’t have your cell phone handy or he may wonder why you didn’t just check the time on the screen.

Photo Credit: practicalowl

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Comment on the Weather

Comment on the Weather Level of Success: 60%
Level of Courage Needed: 7 of 10
Is it raining cats and dogs, snowing piles, or is it a perfect sunny day? One great way to start a conversation is to make a comment about the weather. Be cheerful, not complaining, and make sure to smile and make eye contact if possible. If it happens to be raining, and you have an umbrella, but he doesn’t, offer to share! If it’s bright and sunny, sigh deeply, smile brilliantly, and say something like, “What a gorgeous day!” If he’s interested, he’ll use this as an opening to start a conversation with you.

Photo Credit: oblivion head

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Compliment His Pet!

Compliment His Pet! Level of Success: 90%
Level of Courage Needed: 5 of 10
If the guy brings his pet pooch to the dog park, or brings an oversized lizard on a lead, chances are, he’s used to being stopped by little old ladies and pretty young ladies (like you!) alike. Compliment his perfect puppy and ask if you can pet him or her. This is a great conversation-starter because you can continue to ask questions and engage the fellow for at least a few minutes. Ask questions about the pet’s name, age, breed; comment on the dog’s size, cuteness, and obedience. If the guy is interested, he’ll keep the conversation going. If not, he’ll pack up his pooch and continue on his way.

Photo Credit: Dragan*


Wow, what a beautiful coat your pet has! Pets often mean the world to their owners, and showing genuine interest in something that he loves is a surefire way to his heart. You can even share a cute anecdote about your own pet or a fun fact you know about animals. This approach showcases your caring side and ability to connect over common loves. Often, pet owners are eager to discuss their companions and this could effortlessly lead into discussions about your respective lifestyles, hobbies, or even setting up a pet playdate if things go well.

Famous Quotes

Happiness depends upon ourselves.


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Comment on His Attire

Comment on His Attire Level of Success: 50%
Level of Courage Needed: 7of 10
If you’re seeing him in a public setting, and he’s wearing something you like, tell him! But be specific. Say something like, “I really like those shoes,” and if possible, follow up with a question, like, “Are they Converse?” If he’s still not taking the bait, you can continue asking questions, such as “Where did you find those? They’re so different!” If he’s interested, he’ll go on and on about those shoes, just to keep you talking. When paying a compliment, make sure to sound sincere.

Photo Credit: [ البندري // ♥ QTR

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Ask about the Music

Ask about the Music Level of Success: 60%
Level of Courage Needed: 7 of 10
If you’re at a club or coffee shop with music playing, or if he’s listening to music that you can hear, you can start a conversation by asking him if he knows the name of the song or the band. You can say something along the lines of “I really like this song, do you know who this is?” Or, you can sing along with the song a little bit, and if he’s standing nearby, you can make eye contact, smile, and say, “I love this song,” and let him answer back. Either way, it’s a good way to open a line of communication, and hope he bites back!

Photo Credit: OMG its Shortiie ♥

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Ask about a Friend

Ask about a Friend Level of Success: 70%
Level of Courage Needed: 8 of 10
If the guy you’re after happens to be a friend of a friend, you can start a conversation by asking him about the friend. Feel free to ask a question you already know the answer to, or ask a very general question, like, “When was the last time you saw so-and-so?” or “Did you go to that party at so-and-so’s place last weekend?” Asking about the friend and listening closely to his response will give him a chance to keep the conversation going. It also gives you a chance to follow up with the friend later, to see if he mentioned running into you!

Photo Credit: Abundant Life Photography ~ Rebekah

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Ask for Directions

Ask for Directions Level of Success: 70%
Level of Courage Needed: 7 of 10
Men hate to admit when they’re lost, and love to give directions. If you can sum up the courage, approach him and ask him for directions. You can ask about a specific café or pub, or just for a street, but either way, he’ll be pleased to point you in the right direction, and may even offer to escort you. If he does, bingo! Use the walk to chat about other things, and once you reach your destination, you can offer him a drink or treat, and if the walk went well, maybe even your phone number!

Photo Credit: jghphoto21

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Ask about the Bus/train Schedule

Ask about the Bus/train Schedule Level of Success: 40%
Level of Courage Needed: 5 of 10
This one’s not as successful because it’s so vague he may not realize you’re trying to flirt. Anyone could ask him about a bus or train schedule! That’s why it’s important to use this one carefully. Catch his eye, smile, and walk over. Once you get close, ask him sweetly if he knows when the bus ought to arrive, then as soon as he tells you, if you get a good vibe, you can simply thank him and introduce yourself. If you only ask him about the schedule, he may not get bold enough, or clued in enough, to know he’s supposed to start a conversation with you.

Photo Credit: Intiaz Rahim

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Ask What’s Good

Ask What’s Good Level of Success: 80%
Level of Courage Needed: 7 of 10
If you’ve been eyeing him from across the restaurant, are sitting next to him at the bar, or have been standing in line with him at the coffee shop, ask him what’s good to eat or drink there. You could also ask what he’s having, and comment that it looks good. If it’s a coffee drink, you can ask what’s in it. If he’s interested, he will definitely start a conversation here, and may even offer you a taste!

Photo Credit: Gelchy

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Ask about His Book/magazine

Ask about His Book/magazine Level of Success: 90%
Level of Courage Needed: 8 of 10
If you’ve found him on a plane, in a waiting room, on a bus, or in the bookstore, when he looks up, catch his eye, smile, and ask what he’s reading. Be careful not to interrupt him if he’s deeply involved, though! If it’s an author you’re familiar with, you can jump off and ask him to compare it to the author’s other books, or ask if it’s good. Don’t ask what a book is about, because that’s usually hard to explain. Talking about a book or magazine is a great way to start a conversation because you’ll be talking about something you already know he likes!

Photo Credit: achew *Bokehmon*

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Ask about the Score

Ask about the Score Level of Success: 70%
Level of Courage Needed: 7 of 10
If you’re at a pub, bar, or live sporting event, ask the guy about the score, or to explain a ruling. You can also ask about which team he’s rooting for, or what he thinks of a particular player or coach. Men love to talk about sports, and to give their opinion, so this is a fantastic conversation starter! Even if you loathe sports, pay attention to what he says and be sure to smile!

Photo Credit: Derek Farr ( DetroitDerek )

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Send over a Drink

Send over a Drink Level of Success: 90%
Level of Courage Needed: 9 of 10
If you’re at a restaurant, café, or pub, and you’ve been making eye contact and flirting all night, try sending over a drink. He’ll know right away you’re interested, and will most likely approach, thank you for the drink, and introduce himself. Now’s your chance! Introduce yourself and compliment him in some way, but be sincere and specific. Don’t use a pick-up line or say anything too corny, but try and be clever and charming. I’ve rarely been bold enough to try this, but every time I have, it’s worked!

Photo Credit: |.molly.|

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Ask about His Tech

Ask about His Tech Level of Success: 80%
Level of Courage Needed: 7 of 10
If there’s one thing men love more than sports, it’s technology. They always have the coolest phones, iPods, netbooks, you name it. If the guy you’ve been semi-stalking always has a bit of technology with him, be bold and ask him about it. If it’s an iPod, of course you can ask what’s on his playlist. If it’s a phone or a hand-held gaming device, you can ask what he’s playing. This is a great conversation starter because once you get a man going about his toys, he won’t want to stop talking!

Photo Credit: ..nina.. [back again, but still busy]

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Ask for Help…

Ask for Help… Level of Success: 75%
Level of Courage Needed: 4 of 10
There are many locations where this conversation starter might come into play. Perhaps you’re at the library studying and you spot your guy. This is when you ask for his help to get a book down from the top shelf. Or maybe you’re at the grocery store and can’t quite get the box of cereal you have a coupon for when you can’t believe who you see! Asking a guy for help is a great way to get his attention and make him feel good.


When reaching out for assistance, it instantly creates a connection through an act of kindness. Guys often enjoy feeling useful and coming to the rescue. This doesn't have to be the cliché damsel-in-distress scenario—it's just a practical way to engage him. It could be as simple as needing help with a chore, a technical difficulty, or a work-related question if you're colleagues. By showcasing a touch of vulnerability, you're signaling that you trust his abilities, which can be incredibly flattering and a perfect icebreaker.

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Ask to Sit down…

Ask to Sit down… Level of Success: 60%
Level of Courage Needed: 8 of 10
Whether it’s crowded or not, if you really want to talk to this guy, ask to sit down next to him! Now don’t go making it an awkward situation if, say, there are tons of tables available or he is sitting at a table for two. However, if he is sitting at a long picnic table that has several seats, ask to sit down and introduce yourself.


When approaching, make sure you wear your brightest smile and keep your body language open and inviting. Confidence is attractive, but remember to gauge his reaction. If he seems receptive, slide into the conversation with a light topic. It could be as casual as commenting on the weather or asking his opinion on a common interest. A coffee shop might be a perfect place for this approach, where sharing tables is more common. Just remember, every situation is unique, so adapt your approach to the environment and his body language.

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Talk about School/Summer Vacation

Talk about School/Summer Vacation Level of Success: 70%
Level of Courage Needed: 7 of 10
If you’re taking the same class or sit at the same lunch table with a group of friends, talk about school, homework, or even the teacher. It’s the start of a new school year and the start of new possibilities. If you’ve been wanting to ask this guy out since last year, don’t let the opportunity get away from you again. Ask him how his Summer was and what class he is looking forward to the most.

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Talk about a Big News Event…

Talk about a Big News Event… Level of Success: 65%
Level of Courage Needed: 5 of 10
Whether it’s the trouble in Syria or the trouble with Miley Cyrus, chances are he has an opinion about what everyone else has been talking about. Start the conversation with, “Can you believe what happened?" or "What do you think about this situation?” to get things rolling on the biggest topic that you heard on the news recently.

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Ask about His Tattoo

Ask about His Tattoo Level of Success: 75%
Level of Courage Needed: 8 of 10
If his only visible tattoo says “Mom,” you may want to stay away from this conversation starter! However, if he has something that looks really interesting and unique, this would be a great way to start talking to him. There’s always a story behind someone’s tattoo, no matter what it is, even if they have a tattoo of a dog. Ask him about his tattoo and maybe he’ll get the chance to see yours!

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He Looks like a Celebrity…

He Looks like a Celebrity… Level of Success: 65%
Level of Courage Needed: 8 of 10
This is not only a great way to start a conversation with the guy you like, but also a great way to compliment him. This is especially true if he happens to look like Johnny Depp or Brad Pitt! Though, you don’t want to go overboard by stretching the truth just so he’ll talk to you.

See? There are so many ways to start a conversation with someone new! I’m sure a man would be flattered to be approached by a cute girl, so if you’re brave enough, try just walking up and introducing yourself! Which of these tips have you tried, and did it work? Or is there a conversation starter you’ve used that’s worked, too? How do you approach a new guy and keep him interested? Please let me know!

Feedback Junction

Where Thoughts and Opinions Converge

There is this guy at my school he is in yr9 and im in yr7 but i should be in yr8 i know it sound weird but i like him even though i dont know any think about him and i dont know what to say to him when i see him and yesterday my friend went and started talking to him and she called me over so i went over and all we said to each other was hai i would love to talk to him and get to know him but i dont know what to say to him and i get nevers when i see him at school all the time but i really want to know what to say to him so could yu help me tori xoxo

Well I try to start conversations with him at school.. but I always get so shyy around him.. My heart beats real loud when I see him and he like smiles at me sometimes but welll I dunnno what to do. O.O plus he just got a girlfriend & I just so confused.. but he messages me on fb all the time and we talk alot... Im so confused at the signals.

I like this guy and we used to talk and say hi in the hallways and we had nick names for each other and everything then for some reason that all died off. Its not the same, how do i start it up again?

Okay there is this guy i like but i don't know if he likes me he has already asked out 1 of my friends i think she likes him back and i don't want to be a boyfriend stealer or anything. I don't even think he know me, he is in 1 of my twin sister's classes and he knows her but i don't think he even realizes that im alive. HELP!

2? Really? I don't think that I would notice somebody flirting with me by giving me a pen. I don't think many people would think that him saying "no problem" after thanking him is him rejecting you or not clever.

Hi, so there’s a guy I like. He is super cute and is really smart. But theres a problem, I’m in 7th grade and he’s in 8th. I really like him and I can’t stop thinking about him. He also has a great personality. Whenever we are walking to our next classes in the hallway and we pass each other, he always looks at me and I look at him but our eyes never meet. I like him more and more every day. He also looks at me alot, and now I sit next to his desk so when we switch classes I’ll see him more. He also says hi to me but he doesn’t say hi to any of the other 7th grade girls. I probably thought about him for 99.9% of the day today. I am on spring break and I already miss him. I have a phone but im not sure if he does, and if he does I don’t have his number. I don’t have a Facebook either so there is literally no way of communication unless we actually talk. I won’t see him for another week and three days. I’m going to go crazy. His sister was in my brothers grade. Also the only way I’d see him on weekends is if i go to church on Saturday but I’m not goin on Saturday cuz its Easter. Maybe he’ll be at the Easter mass on Sunday, but I hope at the same time as me. Thanks for reading!

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