30 Ways to Effortlessly Start a Conversation With A Guy

When you’re shy, nervous, and single, it can feel impossible to meet someone you connect with. Striking up a conversation with a stranger is hard enough, but finding something to talk about with a guy you’ve got a crush on feels even more daunting. 

What if you could approach a guy with effortless confidence and ease that leaves him craving to get to know more? With these simple tips, you can. 

Here’s how to talk to a guy (even if you’re shy) in ANY situation: 

How to Start a Conversation With a Guy

Whether you’re looking for a fun date night or a long-term relationship, interesting conversations are the fuel to any romantic attraction. Even the most physically attractive people often struggle with what to say to the opposite sex. 

Starting a conversation with a guy comes down to two main parts: confidence + action. First, build up your confidence behind the scenes. Then use some of these straightforward methods to initiate a discussion. 

You could be one conversation away from a new love interest. Or you could simply meet a new friend or business contact. What do you have to lose? 

Watch our video below to learn how to start a conversation with anyone using these killer conversation starters!

#1 Be bold and make the first move

A lot of women wait for guys to approach them. Some societal norms may have deemed it “unladylike” to initiate a date, or maybe that guys “enjoy the chase.” But, modern surveys show it’s quite the opposite. 

A 2005 study in the Journal of Sex Research found that 72% of men prefer for women to make the first move. Similarly, a 2017 survey on Singles in America found that 95% of men prefer a woman to ask for their phone number. Even more surprising, most men want the woman to initiate the first kiss or sexual encounter. 

Most ladies simply aren’t aware of these preferences. Although every dude is different, the modern shift away from traditional gender roles and courting rituals means that females have a new upper hand in the dating game. 

While most women are waiting for guys to make the first move, you could be the bold one that sets yourself apart. Men are often pleasantly surprised and even impressed when women take the initiative to start a conversation. 

Approaching a guy in public shows you are confident, attractive, and willing to flip the switch on standard dating “rules.” 

Here’s how to turn on your effortless charm and approach him with confidence:

#2 Make eye contact with him

Before beginning a conversation, eye contact lets you test the waters to see if someone is interested. 

• Start by glancing in his direction. 
• If he returns your gaze, hold it for a few seconds, then look away. 
• After a few minutes, make eye contact again. 
• If he returns your look, it’s a good sign he may want to talk to you.

Prolonged eye contact triggers oxytocin release in the brain, which links to increased attraction and arousal, even in strangers. You can use this to your advantage when initiating a conversation with a guy you’re interested in. 

Just be sure not to stare for longer than 3-5 seconds at a time. Otherwise, you may seem socially awkward or a little creepy. 

Pro Tip: Since eyes are the windows to the soul, it helps to understand eye contact cues as much as possible. Learn How to Read People’s Eye Direction and Behavior with the 34 most common eye cues. 

#3 Exchange a warm smile

Studies show that men are most attracted to smiling women. Men perceive a smile as a flirtatious signal that you’re interested in them. 

Before you walk up to a guy to initiate a conversation, send him an easygoing smile with both corners of your mouth raised evenly and your teeth slightly showing. 

If you’re afraid of looking uncomfortable or forcing a grin, it helps to think of something that makes you happy or excited so that your smile appears more natural. 

Pro Tip: Take at least a half-second to form a slow “savor smile.” A quick, most see flashed smile as inauthentic or fake. Learn more about the science of smiling and 9 Tips to Smile Better so you appear warm, relaxed, and genuine.

#4 Read his body language

Once you’ve used eye contact and a smile to demonstrate your interest, it’s time to double-check that he is receptive to having a conversation in the first place. Whether you’re across the room or adjacent to each other at a bar, pay attention to his body language as he responds to your cues.

Signs He Wants to Talk To You (Approach!)	Signs He May Not Want to Talk (Don’t Approach)
Holds your eye contact for more than 1-2 seconds	Averts or avoids eye contact
Returns a grin when you smile at him	Frowns or has a tense facial expression
Turns to part of his body to slightly face you (feet, torso, or head)	Turns away from you or starts a conversation with somebody else
Relaxed arms or open, visible palms	Crossed arms or hidden hands (unless it’s cold, then he might just be keeping warm)

Remember that every guy has different preferences and cues he uses to show interest. Often, men are just as nervous as you are about dating and starting conversations. If you’re getting mixed signals, approach him anyway and see how things go. Worst case scenario, you get another practice run under your belt.

#5 Use these techniques to reduce anxiety

There’s no doubt that approaching the opposite sex can be crazy nerve-wracking. Sweaty palms, an elevated heart rate, and flutters in your stomach are all your body’s way of responding to the discomfort. Thankfully, there are also some proven ways to reduce stress so you can feel calmer and collected before a conversation. 

Try these techniques to keep your cool before approaching him: 

• Deep box breathing: This relaxation technique can quickly reduce your stress levels and heart rate. Deeply inhale for 4 seconds, hold for 4 seconds, then exhale for 4 seconds. Repeat as many times as necessary (in the bathroom or while still at your table in a public place) until you feel more relaxed.
• Hydrate: No, this doesn’t mean you should gulp down another cocktail. Research shows that simply drinking water helps reduce your heart rate, making you feel less stressed and nervous at the moment. 
• Self-affirmation: Internally repeat your favorite affirmation 3-5 times to boost your confidence and remind yourself what an empowered, beautiful woman you are. You can do this in the bathroom mirror, in your car, or before walking to a guy. 
• Laugh: If you’re out and about, try to get in a lighthearted mood before approaching a guy. Ask your girlfriends for a confidence boost or a goofy joke. Maybe call your grandma or your best friend to have them remind you of a super hilarious moment. Laughter can help you feel relaxed and ready to share your best smile. 

#6 Roll back your shoulders and walk calmly over to him

Once you’ve gotten solid signals that he’s interested in you and relaxed your mind, pay attention to your body language as you approach him. This helps set the stage for an excellent first impression and gives you momentum to start a good conversation. 

Even if you are shy, you can still “fake it ‘till you make it” with body language. 

Here’s how to radiate confident body language as you approach a guy: 

• Relax Your Body: Stand up tall, roll your shoulders down and back and try to stay relaxed and expansive. 
• Keep your hands visible: Try to hold only one item (like a purse or drink glass) and keep the other hand free. Visible palms are a social sign that you are trustworthy and calm. This also makes you appear more organized and “put together.”
• Walk the walk: Don’t look like you’re in a rush to get over to him. Instead, portray casual confidence by moving with ease and grace. Find a speed that is relaxed yet deliberate. Allow your hips to sway naturally and embrace your feminine charm.

• Take slow deep breaths: Be aware of your breathing as you move. Slowly breathe through your nose and relax your body. 
• Know where you’re going: If you are approaching a guy, you want to look poised and purposeful in your walk. Decide if you’ll walk up and stand next to him, sit at an empty bar seat, or casually lean over the table when you get over to him. It helps to survey the surrounding social setting ahead of time. 

Pro Tip: If you accidentally trip over your feet, stumble over your words, or do something embarrassing while trying to approach a dude, don’t sweat it! Believe it or not, making a small mistake and laughing at yourself can make him like you more. 

The Pratfall Effect explains why people can be perceived as more attractive when they make small mistakes or clumsy blunders. In a dating setting, it can be endearing to see the little imperfections in someone who may at first seem intimidating or superior.

As a woman, laughing at your small mistake makes you seem more down-to-earth and less “stuck up.” Just try not to trip and fall down any stairs in the process! 

#7 Simply introduce yourself and ask his name

Some things never go out of fashion: introductions are a timeless way to transform a stranger into a friend. Once you know each other’s names, interactions get a little smoother.

You can reach out your hand for a handshake, hold your glass up for a “cheers,” or just nod your head and say a simple opening line like:

• “Hey, I’m Logan. What’s your name?”
• “How’s it going? I’m Britney. Nice to meet you.”
• “What’s up? My name’s Vanessa. What’s yours?”
• (After a short discussion) “By the way, I’m Bianca. What’s your name?” 

You may not want to introduce yourself immediately, so feel free to skip the intros until you start talking for a minute. Then, once you’ve caught his interest, you can ask for his name or see if he asks for yours. 

Or, defy his expectations, skip the intros and be super forward:

#8 Use a conversation starter 

It often seems like a continuous stream of small talk around us. 

“Where are you from?” and “what do you do?” are a little boring. If you want to have a memorable interaction, there a plenty of more unique ways to initiate a good conversation:

• What was the highlight of your day today?
• Have you ever been to an event like this before?
• How do you know the host?
• Working on anything exciting lately?
• How’s that drink/appetizer/artwork/game (whatever they are holding or doing)? 

Having great conversation skills can be one of the best ways to connect with a guy. Knowing what to say is one element, but knowing how to continue a conversation and end it on a high note is a skill you can take with you for life. Here’s how!

Pro Tip: Guys love the sound of their name. After asking a conversation starter question, try adding his name at the end to show that you remember it. For example, “what’s your story, Kevin?” or “so, tell me about you, Sebastian.”  

#9 Ask for his recommendations 

Who doesn’t like to share their opinion? When you ask a man for his advice or recommendation, you instantly demonstrate that you are interested in what he says.

• At a restaurant: What’s your favorite thing on the menu? Have you ever tried the [menu item]?  
• At a bar: Have you ever tried the Montana mule? What’s your favorite thing on tap here?
• At work: Where do you like to go on your lunch break? Do you know any good coffee or sandwich spots? What’s your secret for making so many sales? 
• At school: What’s been your favorite elective class this semester? Do you have any study tips for this upcoming test? 
• At the gym: What’s your favorite supplement for building muscle? What do you think about HIIT training? Are you more into weight lifting or cardio? 

#10 Comment on your surroundings

Psychologists have found that people feel more connected when they have a sense of shared experience. Long before you know if you have anything in common with a guy, your surroundings are an instant source of similarity. 

You and this guy happen to be in the same place at the same time, so use that to your advantage by mentioning: 

• The ambiance of the coffee shop
• The drinks or food at the bar
• A mutual friend or acquaintance 
• How crowded it is 
• A nearby building or artwork
• Wildlife (a particular plant or bird)
• A sign or menu item in a cafe

Pro Tip: With the right conversation tactics and psychological tricks, you can master the art of approaching guys in public. Learn more about How to Talk to Strangers Like a Pro and Avoid Awkwardness.

#11 Compliment him

Who doesn’t like to receive compliments? While you probably shouldn’t gush over a guy, a simple “I like your shoes” or “you have a nice beard” are great ways to flatter him and get the conversation rolling.

Ideally, he will respond with something about where he got the item, or he’ll return a compliment your way. Then, you can follow up with related questions or switch to another topic.

#12 Notice the subtle details

When you want to show a guy that you’re paying attention, notice the details about him that others may not point out.

Does he have a unique vintage band tee? Is he wearing a necklace or bracelet that caught your eye? Is there a book or journal on the table near him? Is he wearing a nice cologne? 

Whatever it may be, look for something subtle to ask him about or to take your compliments to a more personal level.  

Pro Tip: Avoid mentioning anything that might be a source of insecurity. For example, don’t point out a scar or facial blemish. Most importantly, don’t say anything people could accidentally perceive as insulting. 

#13 Pet the puppy

You’d be hard-pressed to find a more straightforward conversation starter than a dog. If he has a dog, you’re in luck. Everyone loves their pets, and he is probably glad to tell you about his pup. 

Head over and ask if you can pet the dog(s), then follow up with questions about their name, age, or breed. Then, you can quickly shift the conversation into asking about his name, places he likes to go with his dog or hobbies he may have that involve animals. 

#14 Mention his celebrity look alike

If he has a celebrity doppelganger or looks slightly similar to a movie star, you can use that as a fun opener to get him smiling. What guy doesn’t want to hear that he looks like Ryan Gosling, Idris Elba, or James Franco? Even if he doesn’t look much like a famous guy, the flattering compliment can quickly initiate some laughter and start a conversation. 

#15 Give him a wink 

Winking is irresistibly sexy. Psychoanalysts say that winks are powerful because they solidify a sense of connection or even shared secrecy. A wink across the room is simultaneously ambiguous and suggestive, which means you’ll leave a guy reeling for answers before you even start talking to him. 

If you want to catch a guy’s interest before starting a conversation, wink at him in a casual way, then look for the cues described above, and then (if he returns interest) approach after a few minutes.  

#16 Ask about his hobbies

When guys talk about themselves, it lights up the same parts of the brain as food, drugs, and sex. If you want to get him talking, ask about his hobbies. 

Here are a few non-awkward ways to bring up his favorite things to do:

• “What’s your current passion project?”
• “What are you into the outside of work?”
• “What skill would you like to master?” 
• “How do you like to spend your free time?”
• “What’s your favorite sport?”

Be sure to follow up his answer with a few more questions. For example, if he says his favorite hobby is acting, ask him if he’s been in any plays or films. If he says he likes to play football, ask what position he plays, what teams he’s played for, or how old he was when he started.

Even if you know nothing about his hobby, showing genuine interest with follow-up questions and listening skills (head nods, “mmm-hmm,” and eye contact) will make him feel important. 

#17 Connect over music 

The soundtracks to our lives say a lot about our people and what inspires us. Music is a super-easy way to connect with a guy, especially if you can find mutual musical interests. 

To initiate a musical conversation, ask him:

• Have you gone to any cool concerts recently?
• What album have you been listening to on repeat?
• What’s your favorite type of music?
• Who are some of your famous musicians of all time? 
• (When music is playing in the environment) Oh, I love this song. Have you heard it before?
• Do you play any instruments? 

If you pay close attention to his overall vibe, you may even be able to bring up a mutual musical interest. For example, if he’s wearing a band shirt, dresses a little punk rock, or hangs out at a record shop, these are all visual invitations for a musical discussion. You may even end up on a concert date! 

#18 Ask for a small favor

Men biologically enjoy helping women. They want to feel like they can “provide” and be of service. There is a “damsel in distress” archetype for a reason: many guys want to feel macho and strong by helping out a lady.

Try asking for a simple favor to initiate a conversation: 

• If you’re headed out of a store and see a cute guy, ask if he can help you carry something heavy to your car. 
• If you can’t get a container open, see if he’ll use his strength to unscrew the cap. 
• If you’re at the gym, see if he’ll help you set up a squat rack or give you a spot. 

Asking for help doesn’t necessarily mean you are needy or incapable. Accepting a small favor from a man helps boost his ego a bit and may give him the confidence to make the next move.

Pro Tip: While guys tend to enjoy helping out ladies, you don’t want to look helpless (“can you help me pump my gas?” … you can handle that on your own), nor do you want to ask for too big of a favor (“hey can you help me carry this couch up 4 flights of stairs to my new apartment?” … that’s more of a request for your brother or a moving company). 

Strike a balance between portraying yourself as an independent non-needy woman and accepting help from a man so he can feel useful. 

#19 Ask how he knows the party host

When you’re loitering on the edges of a party and feeling anxious about talking to anyone, remind yourself that the host or hostess is often the only common denominator between all the guests. 

Asking about a guy’s connection to the party host is a great conversation starter. How did he end up at the party? Maybe they know each other from high school, work, or a band they used to play in. Great, so where did he go to high school? Where does he work? What kind of music does he play?  

Mutual acquaintances or friends are a quick way to connect with someone and learn more about them. Better yet, if you are friends with the host or hostess, ask them if they’ll tell you a bit about the guy and make an introduction. 

#20 Brush by him and say, “excuse me.”

If a guy squeezes in a crowded place between multiple people, you may have an easy “in” to approaching him on your way to the bathroom, bar, or buffet. This trick is one of the oldest in the book (your grandma may have even used it in her day!), yet it still works because it seems candid and cute. 

Put on your actress persona for a second and try to gracefully move past him in a crowd and excuse yourself by bumping into him lightly. Exchange a smile or eye contact, see if he says anything, or loop back around to talk to him after you go to the bathroom

However, be careful that you don’t bump into his arm if he’s holding a drink or cause him to trip.

#21 Talk tattoos

If he’s got ink, he probably likes talking about it. Tattoos are a basic form of self-expression, and they usually have some story behind them. Point out a guy’s tattoo and ask him what it means to him, where he got it done, or what other ink he plans to get in the future. 

#22 Offer to buy his coffee

When you’ve got a slight crush on a man at work or school, you may see them regularly and not know what to say. If you head to a coffee run, try going up to him and saying, “Hey, I’m heading to Starbucks. Can I grab you something?”

Who doesn’t like a warm beverage? Buy him the drink, bring it back to him, and you may even start a fun mini-habit where he reciprocates the favor. 

#23 Ask if you can borrow something

Do you need a piece of paper? A pen? A phone charger? A lighter? Whether at a cafe, school, or an event, you can quickly get a man’s attention by asking to borrow something from him. This opens the door for conversation and gives him the satisfaction of feeling like he helped you. 

How to Start Conversation With a Guy Over Text

So you swiped on his Tinder dating profile or got a guy’s number from that random Instagram DM, now what? To start a conversation over text, you want to avoid boring one-word answers and catch his attention. Here’s how:  

#24 Send a compliment 

If it’s your first time texting someone, a compliment is the easiest icebreaker to warm up to each other and start things off on a good note. Try:

• Hey, it was so fun talking to you yesterday. Want to meet for a coffee sometime this week?
• You looked so handsome in that suit last night
• Our conversations were so interesting. Would love to chat with you again soon😊
• Loved hanging out at the gym yesterday. Lmk if you want to workout together tomorrow

#25 Cliffhanger text 

Pique his curiosity with a bit of a cliffhanger that will leave him wondering what you’re going to say next:

• I just had the best idea for something we should do this weekend! You’re going to love it
• I was listening to Spotify radio, and a song came on that reminded me of you
• The wildest thing happened to me this morning. I have to tell you about it
• You won’t believe who I just ran into

#26 Send him a photo of something that reminds you of him

If you’ve known a guy for a while, you’ve probably discussed a few of his favorite things. As you go about your daily activities, start looking for little reminders of him. Text him a photo of one of his favorite cars you saw on the road, a pic of a restaurant menu you think he’d like, or a dog you saw at the park that looks like his pup. 

You can show you’re thinking about him by sending a quick photo of something he likes. Add a short text like “thought of you” or “don’t you love these?” 

This also demonstrates that you pay attention when he talks, which wins huge points in the listening arena!  

#27 Send a funny meme or GIF

Who doesn’t love a good old meme? If you know a guy’s sense of humor (or at least his favorite TV shows, movies, or musicians), you can easily find a meme or a GIF that will brighten up his day. This is a great way to show your personality and hopefully add some silly laughter to your text thread. 

On iPhone keyboards, you can click the little red emblem with a magnifying glass to bring up GIFs in the text. To find a meme, simply Google “funny meme” or a relevant topic and then screenshot the image, crop it, and text it to him.   

#28 Teasing text

A flirty midday surprise is a perfect thing to pop up on his phone to let him know you’re thinking of him. This text shows him that you have a playful, sexy side that isn’t overly serious: 

• I had a dream about you last night
• My day would’ve been so much better with you in it
• I’ve got a big workout planned for us (send a photo of you at the gym)
• If only you were here right now…
• It’s so cold today. Want to come over and warm me up?

Pro Tip: Add an emoji-like 😜, 😉, or 😂 to show that you are being playful. Here are 45 Emojis You Should Know and Their (Hidden) Meanings.

#29 Reference an inside joke or something he mentioned

Show that you have been paying attention by bringing up a joke or a topic from a previous conversation: 

• I was thinking of watching that Netflix show you mentioned,
• That song you played last night was so good that I want to add it to my playlist. Who sings it again?
• So you like pineapple on pizza, huh?🙄 Usually, that’d be a dealbreaker, but I’ll cut you some slack, lol
• What was the name of that trailhead with the beautiful overlook? I want to hike it this weekend. 

People love to talk about themselves, so this is your opportunity to learn more about his preferences, interests, and sense of humor. 

#30 Reference his social media

You want this guy to know that you checked out his social media pages, but you don’t want to come across as a stalker. Strike a balance by mentioning a newer post and complimenting his vibe. 

• I loved your last Facebook post about pushing toward goals. I’m a sucker for motivational speeches too
• I was just looking at your Instagram, can’t lie… you’re super hot😉
• That Snapchat/IG/TikTok video of your monologue was so incredible! You should post more like that

#31 Ask a question

Psychologists have repeatedly found that asking questions makes you more likable. When in doubt, just shoot a text with a random question and see where it goes. Here are 257 Juicy Questions to Ask Your Friends (or boyfriend). 

Key Takeaways: How to Talk to a Guy with Confidence 

Online dating can be incredibly frustrating, but starting a conversation in public can be equally as daunting. With so many people staring at their phones or avoiding eye contact, how do you know if somebody is interested in you? And what the heck do you even say?

Try a few of these time-tested tips to overcome your anxiety or nervousness when talking to guys, 

• Be bold and make the first move: Even if you forget every other tip for starting a conversation with a guy, this tip alone could transform your dating life. Stop waiting for them to come to you and take action to show you’re interested. Most guys report wanting women to make the first move, so set yourself apart and do it! What do you have to lose? 
• Use body language as your gauge: The easiest way to gauge his interest in you is to learn to read him. Is he returning your eye contact? Reciprocating your smiles? Turning to face you? The more you study body language, the better chances you have at approaching the right guys in the first place. 
• Express interest: Dudes love to talk about their interests and passions. Avoid making it all about you! Instead, ask him questions, notice subtle details about him, and mention things you may have discussed in past conversations. When a guy feels like you genuinely want to get to know him, it opens up deeper conversations and leaves him wondering about you, too.
• Ask for help and recommendations: Males want to help females whenever possible. Even in small daily interactions, guys want to feel like the macho hero of a story. Play into his ego a little bit by asking for help lifting something heavy or getting his opinion on the best thing on the menu. 

Once you’ve started a conversation, you must know how to keep it going. If you want to be more charismatic and stand out in the dating game, learn How to Have and Hold a Dazzling Conversation that will leave him excited for more.