30 Ways to Effortlessly Start a Conversation With A Guy

Learn 30 effortless ways to start a conversation with a guy over text or in person. Build confidence with smiles, eye contact & openers—backed by science. Spark attraction now!

Imagine you’re at a party, spot a great guy across the room, but your nerves kick in and words vanish. What if a few simple tweaks—like a warm smile and bold eye contact—could turn that moment into an exciting chat? Discover how to start a conversation with a guy with confidence in these 30 science-backed tips.

Your Step-by-Step Guide to Approaching Him with Confidence

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.

Turns out, a 2017 survey on Singles in America (source) found high percentages of men appreciate women making bold moves, such as asking them out. 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.

In fact, approximately 30% of U.S. adults have used an online dating site or app (source), where conversation initiation is completely normalized. And here’s something fascinating: 64% of men who used dating apps felt insecure due to the lack of messages they received (source), compared to 41% of women. That means when you make the first move, you’re actually helping ease his anxiety too.

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 can increase feelings of attraction and arousal (source), even in strangers. Use this simple trick when you start talking to a guy you like.

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

A study found that men rated smiling women as the most sexually attractive female emotion expression (source), while women rated smiling men as the least sexually attractive male emotion expression. According to Jessica Tracy, Associate Professor of Psychology at the University of British Columbia, “Men thought happiness was the most attractive female emotion, but women found the smile on a man’s face the least appealing.”

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, flashed smile looks 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 you respond to your cues.

Research from Monica M. Moore, Professor of Psychology at Webster University, found that women display an average of 4.5 nonverbal signals to communicate romantic interest. Guys use similar cues!

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.

Did you know that around 12% of U.S. adults report regular feelings of worry, nervousness, or anxiety every day or most days (source) And 7.1% of U.S. adults had social anxiety disorder in the past year (source), which directly impacts the ability to approach strangers or start conversations.

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 (source) 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 drinking water can influence heart rate in certain physiological contexts (source), helping you feel less stressed.
• 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 are plenty of more unique conversation starters to use when talking to a guy:

• 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)?

As social anthropologist and ‘Flirtologist’ Jean Smith explains in her TEDx talk on The Science of Flirting, “Humour, specifically a shared sense of humour, is really important” in flirting. Look for ways to bring lightness and laughter into your opening lines.

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.”

Conversation Starters for Specific Situations

Knowing what to say to start a conversation with a guy depends heavily on where you meet him. Here are targeted conversation starters for the most common scenarios:

At a Party

• “How do you know [host’s name]?”
• “Have you tried the [food/drink] yet? It’s amazing!”
• “I love this song! Do you know who sings it?”
• “What brings you here tonight?”

At Work or School

• “What project are you working on right now?”
• “Did you catch that meeting/lecture? What did you think?”
• “Where do you usually grab lunch around here?”
• “I’m heading to [coffee shop]. Want anything?”

At the Gym

• “Mind if I work in between your sets?”
• “How’s your workout going today?”
• “Do you have any tips for [specific exercise]?”
• “What’s your favorite way to train?”

At a Coffee Shop or Café

• “Is that seat taken?”
• “What are you reading/working on?”
• “Have you tried their [menu item]? I’m trying to decide what to order.”
• “This place has great vibes, right?”

At a Bar or Club

• “What are you drinking? Is it any good?”
• “Are you here with friends or flying solo tonight?”
• “Have you been here before? I’m trying to figure out this place.”
• “Want to grab the next round together?”

#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 (source). 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? A genuine compliment is one of the easiest ways to start a conversation with a guy and make an instant connection. 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.

The key is authenticity. Choose something you genuinely appreciate:

Style compliments:

• “That’s a great jacket. Where’d you get it?”
• “I love your sneakers—are those the new [brand]?”
• “Your style is really put together.”

Skill or talent compliments:

• “I overheard you talking about [topic]—you clearly know your stuff!”
• “That was an impressive presentation earlier.”
• “You’re really good at [activity I observed].”

Personality compliments:

• “You have a great energy—very welcoming.”
• “I appreciate how thoughtful that comment was.”
• “You seem like someone who’s really passionate about what they do.”

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 (source) are powerful because they solidify a sense of connection or even shared secrecy. It’s flirty and mysterious, and he’ll be dying to know what you mean.

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.

30 Questions to Ask a Guy: Icebreakers, Fun, and Deep Topics

Once you’ve started talking, asking the right questions keeps the conversation flowing naturally. Here are open-ended questions organized by category to help you connect on multiple levels:

Icebreaker Questions (Light & Easy)

Perfect for first conversations when you’re just getting to know him:

• What’s the best thing that happened to you this week?
• If you could have dinner with anyone, dead or alive, who would it be?
• What’s your go-to karaoke song?
• Are you more of a morning person or a night owl?
• What’s the most interesting place you’ve ever visited?

Questions About His Passions

People light up when they talk about what they love:

• What are you most passionate about right now?
• If you could master any skill overnight, what would it be?
• What’s a hobby you’ve always wanted to try?
• What’s the best advice you’ve ever received?
• What achievement are you most proud of?

Fun and Playful Questions

Add humor and personality to your chat:

• If you were a superhero, what would your power be?
• What’s the most embarrassing thing that’s happened to you?
• In a zombie apocalypse, what’s your survival strategy?
• What’s your guilty pleasure TV show or movie?
• If you could only eat one food for the rest of your life, what would it be?

Deep Conversation Questions

Once you’ve built some rapport, go deeper:

• What’s something you believe that most people disagree with?
• What motivates you to get out of bed in the morning?
• What do you value most in a friendship?
• What’s a risk you’ve taken that you’re glad you did?
• How do you define success for yourself?

Questions About Interests and Hobbies

Informing others about oneself activates brain regions associated with reward (source), similar to food, money, and sex. Ask about his hobbies and he’ll chat for days.

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 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 favorite 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

Guys love to help women out. 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. Letting him do a small favor strokes his ego and can nudge him 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.

Text Like a Pro: Openers That Spark Replies Instantly

So you swiped on his Tinder dating profile or got a guy’s number from that random Instagram DM, now what?

With approximately 30% of U.S. adults having used an online dating site or app (source), knowing how to start a conversation with a guy over text has never been more important. To start a conversation over text, you want to avoid boring one-word answers and catch his attention.

Here’s the interesting part: 54% of women who used dating apps in the past year felt overwhelmed by the number of messages they received (source), compared to 25% of men. This tells us that men are usually the ones initiating online—so when YOU start the conversation, you immediately stand out.

Here’s how to text a guy you like:

How to Start a Conversation With a Guy on Dating Apps

On Tinder:

• Reference something specific from his profile: “I see you’re into rock climbing! What’s the scariest route you’ve done?”
• Use humor: “Your dog is adorable. Can I date both of you? 😄”
• Ask an engaging question: “Okay, hot take from your profile—is [opinion he mentioned] really controversial or are you just being bold?”

On Bumble:

• Since you have to message first, make it count: “Your travel photo from [place] is amazing! What was the highlight of that trip?”
• Compliment + question combo: “Great smile in that pic! What’s something that always makes you laugh?”

On Hinge:

• Comment on a specific prompt: “Your answer about [prompt topic] made me laugh. Have you always been this [funny/adventurous/honest]?”
• “I had to swipe right when I saw you’re into [shared interest]. What got you into that?”

On Instagram DMs:

• React to a story: “Just saw your story about [topic]—I totally relate! Have you tried [related thing]?”
• Keep it casual: “Hey! Your feed is really cool. Are you a [his apparent profession/hobby]?”

#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? Once you know what shows or movies he likes, pick a meme that’ll make him laugh. 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

Want an easy way to be more likable? Ask questions. 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).

FAQs: How to Start a Conversation with a Guy

How do you start a conversation with a guy without being awkward?

The secret to avoiding awkwardness is preparation + confidence. Before approaching him:

1. Use the anxiety-reduction techniques mentioned earlier (deep breathing, self-affirmation)
2. Have 2-3 conversation starters ready so you’re not scrambling for words
3. Remember that he’s probably just as nervous as you are
4. Focus on being genuinely curious about him rather than trying to be perfect

If awkward silences happen, don’t panic. You can:

• Ask a follow-up question about what he just said
• Comment on something in your environment
• Share something related to the conversation
• Laugh it off and say, “I’m a little nervous—you seem really cool!”

Honesty about your nerves can actually be endearing and breaks the tension.

What’s the best way to start a conversation with a guy you like?

Start with a warm smile and eye contact to signal your interest. Then use one of these proven openers:

• Give him a genuine compliment about something specific (his style, something he said, his skills)
• Ask for his recommendation or opinion on something
• Comment on your shared environment or situation
• Ask an open-ended question about his interests

The key is to show authentic interest while being yourself. He’ll appreciate your confidence in making the first move!

How do you start a conversation with a guy online?

On dating apps and social media:

1. Reference his profile: Mention something specific from his photos or bio
2. Ask an engaging question: Go beyond “hey” with something that requires a real answer
3. Use humor: A playful or funny opener stands out from generic messages
4. Be specific: “I loved your hiking photo from [place]!” beats “Nice pics”
5. Keep it light: Save deep conversations for after you’ve established rapport

Remember: 64% of men feel insecure about lack of messages (source), so your message will likely be very welcome!

What should I say to a guy to start a conversation?

The best conversation starters depend on the context, but here are universal options:

In person:

• “Hi, I’m [name]. What brings you here?”
• “I couldn’t help but notice [specific detail]. Tell me about it!”
• “This might sound random, but [observation about environment]. What do you think?”

Over text:

• “Hey! [Specific thing you noticed/liked]. I had to reach out!”
• “Quick question: [something related to shared interest or his profile]”
• “[Something funny/interesting] made me think of you”

The key is to be specific rather than generic. Personalized openers get better responses than “Hey, what’s up?”

How do you keep a conversation going with a guy?

Once you’ve started talking:

1. Ask open-ended questions: Questions that require more than yes/no answers
2. Listen actively: Really hear what he’s saying and ask follow-up questions
3. Share about yourself too: Conversation is a two-way street
4. Find common ground: Look for shared interests or experiences
5. Use the thread technique: Take something he mentioned and explore it deeper

For example, if he mentions he likes hiking:

• “What’s the best hike you’ve done?”
• “Do you prefer mountains or forests?”
• “I’ve been wanting to try [local trail]. Have you been there?”

To learn more conversation skills, check out How to Have and Hold a Dazzling Conversation.

What if he doesn’t seem interested in talking?

Pay attention to his body language and verbal cues:

Signs he’s not interested:

• Very short, one-word answers
• Avoids eye contact
• Turned away from you physically
• Checking his phone frequently
• Says he needs to go or has somewhere to be

What to do:

• Politely excuse yourself: “Well, it was nice chatting! Have a great day.”
• Don’t take it personally—timing matters, and he might just be having an off day
• Move on with confidence—the right person will be excited to talk to you

Not every conversation will lead somewhere, and that’s okay! Each interaction is practice for the next one.

Confidence Essentials: The Top Tips to Chat Effortlessly

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. With men reporting that they appreciate when women initiate, 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.
• Master the art of open-ended questions: The difference between “Do you like your job?” and “What do you love most about your work?” is huge. Open-ended questions invite storytelling and keep conversations flowing naturally. They show you’re genuinely interested in his thoughts, not just checking boxes.
• Handle awkward silences with grace: Every conversation has pauses—they’re natural! Instead of panicking, use the silence to think of a follow-up question, share a related story, or simply smile and ask, “So, tell me more about that.” Confidence during brief silences actually makes you more attractive.
• Ask for help and recommendations: Guys love to help women out. 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.

Take Your Conversation Skills to the Next Level

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