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How To Start A Conversation With A Guy You're Interested In

A Gay Man's Guide To Chatting Up A Hottie


Feeling shy and nervous about approaching that cute guy you've been eyeing? Don't worry, we've got your back with some fabulous tips to make that first move and leave him wanting to know more!


Master the Art of Chatting Up Your Crush


Whether you're after a fun date night or a long-term love, interesting conversations are essential. We're all about confidence + action. Boost your self-assurance and then dive into these amazing conversation starters. You might just find a new love interest or even an awesome new friend!


1. Be a Conversation Trailblazer: Make the First Move


Stop waiting for Prince Charming to approach you! Men actually love when someone else takes the initiative. Our fictional friend, Mark, says, "I'm always thrilled when a guy comes up to me first. It shows he's confident and isn't afraid to challenge the status quo." So go ahead, be a conversation trailblazer and set yourself apart!


2. The Power of Eye Contact: A Little Look Can Go a Long Way


Those dreamy eyes can do wonders for you! Our friend, Luke, advises, "Catch his gaze, hold it for a few seconds, and then look away. Repeat this a couple of times, and you'll know if he's interested." Just remember not to stare for too long (3-5 seconds max), or you might come off as a little creepy. Master the art of eye contact cues to make the most of this technique.


3. Flash That Irresistible Smile: Show Him You're Interested


Smiles are a guy's best friend, and they can work wonders when starting a conversation. Our charming pal, Daniel, shares, "When a guy smiles at me, it's like an instant connection. It's a sign that he's approachable and open to talking." Before approaching your crush, flash an easygoing smile with both corners of your mouth raised evenly and your teeth slightly showing. Remember to think of something that makes you happy so that your smile appears more natural.


Pro Tip: The Savor Smile


Make sure to take at least half a second to form a slow "savor smile." A quick, flashed smile can come across as inauthentic or fake. Learn more about the science of smiling and 9 Tips to Smile Better, so you appear warm, relaxed, and genuine.


Let's Get This Chat Started!


Now that we've covered the essentials, it's time to take a deep breath and put these tips into action. Go on, unleash your inner flirt and start chatting up your crush. Remember that the modern shift away from traditional gender roles and courting rituals means that you have a new upper hand in the dating game. Embrace your confidence, make that first move, and show him just how amazing you truly are. You've got this, darling! 🌈💕


Understanding His Signals and Calming Your Nerves


Decode His Body Language: Is He Into You?


Once you've caught his eye, it's time to read his body language. Pay attention to his response to your cues, and look for signs that he's interested. Remember, every guy is different and might show interest in various ways. If you're getting mixed signals, approach him anyway; it's just another opportunity to practice!


Keep Calm and Carry On: Anxiety-Busting Techniques


We know approaching a guy can be nerve-wracking, but don't worry, we've got some proven techniques to help you feel calm and collected:


  • Deep box breathing: A quick way to reduce stress and lower your heart rate.
  • Hydrate: Drinking water can help you feel less stressed and nervous.
  • Self-affirmation: Boost your confidence by repeating empowering affirmations.
  • Laugh: Get in a lighthearted mood before approaching him, with the help of friends or funny memories.


Strut Your Stuff: Confident Body Language


Now that you're feeling calm and confident, pay attention to your body language as you approach your crush. Radiate confidence with these tips:


  • Relax Your Body: Stand tall, roll your shoulders back, and stay relaxed.
  • Keep Your Hands Visible: Hold only one item, like a drink, and keep the other hand free.
  • Walk the Walk: Move with ease and grace, portraying casual confidence.
  • Take Slow Deep Breaths: Be aware of your breathing as you approach him.
  • Know Your Destination: Decide where you'll stand or sit when you reach him, and survey the social setting.


Pro Tip: Embrace Your Imperfections


If you trip, stumble, or make a small mistake while approaching your crush, don't sweat it! Laughing at your imperfections can actually make you more attractive, thanks to the Pratfall Effect. Embrace your endearing quirks and keep your head held high!


Armed with these tips, you're now ready to approach that special guy and start a conversation. Embrace your inner flirt, and remember: confidence is key! Good luck out there! 🌈💕


Timeless Introductions: Name Exchange


Introductions are a classic way to turn a stranger into a friend. Once you know each other's names, the conversation becomes smoother. Try a simple opening line like:


  • "Hey, I'm Logan. What's your name?"
  • "How's it going? I'm Bret. Nice to meet you."
  • "What's up? My name's Van. What's yours?"


Feel free to introduce yourself after talking for a minute, and then exchange names.


Stand Out with Unique Conversation Starters


Ditch the boring small talk and try some unique conversation starters to make your interaction memorable:


  • 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're holding or doing)?


Pro Tip: Use his name in the conversation to show you remember it, like "What's your story, Kevin?" or "Tell me about you, Sebastian."


Engage Him with Recommendations


People love sharing their opinions, and asking a guy for his advice or recommendation shows you're interested in what he has to say. Tailor your questions to your environment:


  • 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?"


Bond Over Shared Surroundings


People feel more connected when they share experiences. Use your surroundings as a source of instant similarity, discussing things like:


  • The ambiance of the coffee shop
  • The drinks or food at the bar
  • A mutual friend or acquaintance
  • How crowded it is
  • Nearby buildings or artwork
  • Wildlife (plants or birds)
  • Signs or menu items in a cafe


Compliment Him


Everybody loves compliments! A simple "I like your shoes" or "you have a nice beard" can flatter him and get the conversation rolling. Ideally, he'll respond with more information or return a compliment, allowing you to continue the conversation.


Pay Attention to Subtle Details


Show you're paying attention by noticing details about him that others might not:


  • Unique clothing items
  • Interesting accessories
  • Books or journals nearby
  • Nice cologne


Pro Tip: Avoid mentioning anything that might be a source of insecurity or could be accidentally perceived as insulting.


Mention His Celebrity Look-Alike


If he resembles a celebrity, use that as a fun opener to make him smile. Even if he doesn't look much like a famous person, the flattering compliment can initiate laughter and start a conversation.


Try a Wink

A wink can solidify a sense of connection or shared secrecy. Wink casually to catch his interest, look for cues, and then approach if he returns interest.


Ask About His Hobbies


Guys enjoy talking about their interests, so get him chatting by asking about his hobbies. Here are some conversation starters:


  • "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?"


Follow up his answers with more questions and use active listening skills to make him feel important.


Connect Over Music


Music is an easy way to connect with a guy, especially if you can find mutual interests. Try these conversation starters:


  • "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?"
  • "Do you play any instruments?"


Pay attention to his overall vibe for clues about mutual musical interests, which could even lead to a concert date!


Ask for a Small Favor


Men often enjoy helping others, so asking for a simple favor can be a good conversation starter:


  • Ask for help carrying something heavy.
  • Request assistance opening a container.
  • At the gym, see if he'll help you set up equipment or give you a spot.


Pro Tip: While it's okay to ask for help, don't come across as helpless or ask for too big of a favor. Strike a balance between portraying yourself as an independent person and accepting help so he can feel useful.


Ask How He Knows the Party Host


Inquiring about a guy's connection to the party host can be a great conversation starter. Knowing how they met could lead to discussions about high school, work, or shared hobbies. Mutual acquaintances or friends are an easy way to connect with someone and learn more about them. You can also ask the host to introduce you or tell you more about the guy.


Brush by Him and Say, "Excuse Me."


Gracefully moving past a guy in a crowded space and lightly bumping into him can create an opportunity for interaction. Exchange a smile or eye contact and see if he says anything. Loop back around to talk to him after you've completed your task. Just be careful not to cause any accidents, like spilling his drink.


Talk Tattoos


If he has tattoos, he might enjoy discussing them. Tattoos usually have a story behind them, so ask him about the meaning, where he got it, or his plans for future tattoos.


Offer to Buy His Coffee


If you see a guy you're interested in at work or school, offer to buy him a coffee when you're heading out on a coffee run. This could lead to a fun routine where you take turns buying each other drinks.


Ask if You Can Borrow Something


Whether you're at a cafe, school, or an event, asking to borrow something from a guy can be an easy way to start a conversation. This approach allows him to feel helpful and gives you an opportunity to connect.


How to Start a Conversation with a Guy Over Text


Starting a conversation over text requires some creativity and confidence to grab his attention and keep the conversation going. Here are some tips to help you break the ice:


Send a Compliment


A compliment is an easy and friendly way to break the ice. Examples of compliment texts:


  • Hey, it was great talking to you yesterday. Want to grab coffee sometime this week?
  • You looked really handsome in that suit last night.
  • Our conversations were so interesting. I'd love to chat with you again soon! 😊
  • Loved working out with you yesterday. Let me know if you want to hit the gym together tomorrow.


Cliffhanger Text


Spark his curiosity with a cliffhanger text that leaves him wondering what's 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.


Send a Photo of Something That Reminds You of Him


Show him you're thinking about him by sending a photo of something he likes or that reminds you of him. This demonstrates that you pay attention when he talks, which can be a major plus.


Send a Funny Meme or GIF


Sending a funny meme or GIF is a lighthearted way to engage with him and show your sense of humor. Choose a meme or GIF that relates to his interests or something you've discussed.


Teasing Text


A flirty, teasing text can be a fun way to show your playful side without being too 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?


Remember to add emojis like 😜, 😉, or 😂 to convey playfulness.


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 use this opportunity to learn more about his preferences, interests, and sense of humor.


Reference his social media


Strike a balance between showing interest and not coming across as a stalker 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.


Ask a question


Asking questions makes you more likable. When in doubt, just send a text with a random question and see where it goes.


Key Takeaways: How to Talk to a Guy with Confidence

  • Be bold and make the first move: Most guys report wanting women to make the first move, so set yourself apart and do it!
  • Use body language as your gauge: The more you study body language, the better chances you have at approaching the right guys in the first place.
  • Express interest: Ask him questions, notice subtle details about him, and mention things you may have discussed in past conversations.
  • Ask for help and recommendations: Play into his ego by asking for help lifting something heavy or getting his opinion on the best thing on the menu.


Once you've started a conversation, focus on keeping it going. 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.

Michael Alvear • May 13, 2023
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