girl texting guy learning how to start a conversation

How to Start a Conversation with a Guy— 20 Ways to Keep the Conversation Going over Text!

Learning how to start a conversation with a guy can oftentimes feel intimidating.

Girls, please know, boys aren’t as judgmental as you may think— they aren’t constantly analyzing every text you send over or every sentence you speak. So, breathe and be what you are best at— express what your heart desires to talk about and ask what you genuinely want to know without a pretentious gimmick.  

The anxiety, judgment, and fear of rejection often set us back and away from our love interest! The conversation seemingly starts at an awkward “hi!” and stops at a miserable “Bye.” 

We are constantly trying to be interesting, intellectual, funny, charming, cute, and sharp, but failing miserably. You want to speak every word with utter perfection, whether it justifies your personality or not.  

girl texting guy while sitting on the stairs

Trying to force something without nature will probably never work in your favor. A true conversation only needs your genuine and shameless self— unapologetic and unabashed. 

Trust me, your boy crush would enjoy talking to your most authentic self more than some to-be-chic. 

Easier said than done, right? It’s still scary to put yourself out there for judgment and rejection. That being said, starting a conversation itself is quite a do-or-die situation— It definitely feels like one!

You don’t want to seem boring with a simple hi! However, you also don’t know what’s the most exciting conversation starter that will mop your crush’s world. 

I got your back, girl. This article will take you through every hook and crook of “How to start and continue a conversation with a guy you like.”

How to start a conversation with a guy over text?

Texting has become an intrinsic part of today’s dating world, and it’s definitely not a bad thing! It’s no secret that meeting someone in-real-life is bound to get awkward and clumsy. At times like this, online dating serves as a platter of fruitful luck.

However, starting a conversation may sweat your neck. “Hi,” “Hey,” “Hello,” and “How are you?” have become so generic that they go unnoticed heavily. 

Studies suggest that almost 84% of online users don’t respond to “Hi!” at all. In the crowd of all the messages your boy crush receives, a “Hi” doesn’t stand a chance. A generic message wouldn’t allow you to stand out despite your enchanting personality. 

To stand out and start an interesting conversation, a creative and natural conversation starter is a must to catch your crush’s interest. 

How to hold a conversation with a guy? Don’t start with a “one-word answer” question. 

  • “How was your day?” Fine.
  • “Did you go outside today?” Yes.
  • “Did you eat?” No.
  • “What are you doing?” Nothing
  • “Do you like coffee?” Yes. 

Although some individuals may turn these one-word replies into engaging conversations, others may get disheartened. If you are in the same boat, don’t send one-word reply texts. Moreover, don’t expect a detailed answer to a one-word question either. Instead, ask open-ended questions. For instance, 

  1. “What did you do all day long?” 
  2. “What was your best experience outside today?
  3. “Did you eat sushi again? Why do you like sushi so much?
  4. “Between sushi and sex, what would you choose and why?”
  5. “How do you like your coffee?”

These open-ended questions will allow intriguing revelations and fascinating change of events. 

How to make conversation with a guy? Read your room and read the man!

It would be futile to talk about astrology with a guy who doesn’t find zodiac signs interesting. There’s always a possibility of different interests and tastes. Read him and whatever there is to him to initiate a more captivating conversation. 

couple talking in the morning

For instance, you can read through his Instagram or tinder bio to know his interest and personality or, perhaps, surf through his IG feed. Posts can tell many stories. 

  • If his profile is an entanglement of coffee, nature photography, sunsets, and mountains, you have to talk about traveling, his best city, his best vacation, his adventures, etc. 
  • Talk about food & recipes if he posts pictures of dishes. 
  • Talk about fashion if you constantly find him well-dressed. On the go, compliment him at the same time! 
  • If your boy crush isn’t active on social media, bring that to light. 
  • If he’s into poetry— rhythm with him, send him sweet poetry or ask about his favorite author’s work. 

Tinder pretty much gives away your crush’s bio, his likes, dislikes, and hobbies on a platter. Use that information to start the conversation! 

  1. “I have been to the Himalayas, too! Where did you click that photo?” 
  2. “Enchiladas are the chef’s kisses! Do you have a Mexican restaurant in mind here in Amsterdam? I have been dying to have a proper Mexican meal!”
  3. “Mind If you join the adventure?” 
  4. “Did you make that dish yourself? Please, oh god, please— tell me the recipes or teach me!”
  5. “Okay, Monsieur, I have seen fashion, but where did you get that jacket from? It’s Muah!” 
  6. “Tell me all about it— your disinterest in social media; I might have a similar opinion.” 

Truth is, there’s so much to talk about— endless topics to discuss, argue, share, and rant about. You don’t even have to try; it’s literally served on a golden platter of today’s online dating world. 

What to say to a guy you like? Would you mind a compliment?

No, sir, no! Do go ahead and don’t stop! Who doesn’t like compliments, words of endearment, acknowledgment, and appreciation? Certainly, not me and most certainly, not your boy crush either. 

So, start with a genuine compliment. 

  1. “I don’t know what I’m more impressed with— your photography skills, your photos, your dedication, or your traveling list.”
  2. “I could look at those food photos for hours. How did you learn to cook? They all look so mouth-watering. Food porn, isn’t that what it’s called?”
  3. “You are quite the haute chef, sir!” (Haute as in hot)
  4. “That jaw is sharper than my counter’s edge.” 
  5. “You are very impolite, sir! I happen to like it!”
  6. “Your eyes… they change colors, like magic. It’s hypnotizing.”
  7. “Forgive me for being so impolite, but you are the most delicious man I have ever seen.”
  8. “You sing beautifully. Pure orgasm.”

A compliment will surely bring a smile to his face, and he might as well reply. However, I ask you to refrain from complimenting vaguely or with dullness. Don’t just compliment his looks, but his characteristic charisma. 

  • Appreciate his art
  • Acknowledge his effort
  • Flirty, sexy, and naughty compliments can start a great conversation. 
  • Be a little bold with your compliment. 
  • Everyone’s appreciating his online image already, be the one to compliment his very core and authentic self. 

How to start a flirty conversation with a boy? Be bold, flirty, daring, and confident.

  1. “I would best describe myself as an overly passionate girl who’s definitely interested in you.”
  1. “Can we meet again without a coincidence? My apologies, but my heart seems overly interested in knowing you.” 

Shyness would never allow you to speak your heart. If you let shyness rule the conversation, you will turn it into a tragic episode. It would be dull, awkward, and confusing for the guy.  

  • Instead, be confident with what you are about to say. 
  • Be bold when it’s time to flirt your way into his heart.
  • Be a little more daring to text him first. 
  • Be confident in your skin and in your essence. 
  • Be confident in your existence. 

How to text a guy to start a conversation?

Sometimes, letting go of old-dating rules will do you a significant amount of good. So, break the norms! 

  • It’s 2022, and girls are equally likely to make the first move. So, don’t sulk over an unreceived message; instead, be the one to text first. 
  • Break the three-day rule, and ask him to meet you again. 
  • It’s not offensive to leave a sexy compliment for him. Just be sure to ask for consent first.
  • Ask him out if you don’t want to play around the bush and continue online chatter! Direct and to the point. 

Don’t go overboard.

Being confident is one thing, but being too clingy is entirely another. Once you have made the first move, wait for his reply. Allow him the space to think over and come up with an answer before you jump to a conclusion. 

  • Don’t text him again and again. He will reply back to you when he’s free to chat. 
  • Don’t nag. 
  • Don’t allow your ego to stop you from texting. If he hasn’t replied to you in a while and it seems unusual for his personality— ask him before doubting him. 

How to talk to a guy you like? Debate your way into his heart

Yes, you heard it! You have to agree; debating and arguing develop a weird and intense tension between two people. 

The tension literally burns the room, and all that’s left behind is you and your counter-attacking boy crush. Take it from me; I date every guy who surpasses me in an argument. It’s infuriating but also kind of hot!

So, this time, attack him with an intriguing debate instead of sugar-coating your text. 

  1. “I think instant coffee is just as good as freshly-brewed coffee. I don’t see much difference.” 

If he’s a coffee aficionado, he will lose his shit and have multiple arguments ready for you. That’s what romance needs to bloom— furious tension, uncontrollable emotions, and hidden attraction. 

  1. “No way summer is better than winter. Winter rules!” 
  2. “Social media isn’t as bad as you may think.”
  3. “Between introverts and extroverts— introverts are bound to win when it comes to creativity.”
  4. “No, I think pineapple is fine with pizzas. In fact, it’s all the more delicious.” 
  5. “Peaky blinder and money heist suck. Bite me.”

The cute banter and his defense will woo your heart. Boys are cute when they argue and fail/win. These debates don’t necessarily have to be something you strongly believe in— They simply need to trigger his angry pout. 

Debates would maintain an exhilarated conversational flow— which is accurate and full of emotions. Through these arguments, you would also get to know your crush’s beliefs and ideology. 

Don’t stop yourself at hilarious banters. Once you are both comfortable, you can discuss more complex topics to learn from each other and understand each other’s personalities. For instance, discuss feminism, legalizing weed, prostitution, polygamy, etc. 

How to continue a conversation with a guy you like? Find common ground, similar interests, and hobbies. 

While debating will increase tension between you two, finding common interests and hobbies will connect you both emotionally. 

  1. “Wow, you seem to love Freddie Mercury! Have you listened to ‘Somebody to Love?'” It’s a masterpiece. 
  2. “I’m into classical music, too. We should definitely try singing together sometimes or start a band together.”
  3. “I have been planning to go on a cultural voyage in Asia. Can you suggest a good itinerary of the continent?
  4. “Dark chocolate slays! Tell me about it.” 
  5. “Here’s a song you would love, love, and love!”
  6. “I absolutely love Suga. You got to listen to Daechwita.”
  7. “Your cutlery collection is muah!” Where did you get all these antiques from?”

Your boy crush would love to discuss something he’s passionate about! So, dig the dug and get juicy details on his likes and dislikes. 

How to have a conversation with a guy? Sometimes, being random and weird is good.

It’s always “Hi, I love your profile.” and never “Do I look like a koala bear?” 

I always say it’s better to be weirdly fascinating than boringly mediocre. So, embrace your weird self and introduce that very personality to your boy crush. 

A random question has more chances of starting an interesting conversation than a numb “Hi.” So, be as weird as your character allows you to be, and he might dig that persona more than you may think. 

  1. “Who would you rather be— Trump or homeless? 
  2. “How would you like to die?”
  3. “If you had to escape prison, what would be your master plan?”
  4. “Do you think you can escape prison?”
  5. “religion or science?”
  6. What’s the pettiest thing you have ever done in your life?”
  7. “Who is sexier— Sherlock or Damon from TVD?”
  8. “What’s the weirdest sex you ever had?”
  9. “Villains or heroes?”
  10. “Dogs or cats?”
  11. “Do you think aliens exist?”
  12. “What do you think happens after death?”
  13. “Let’s invent the time machine and travel to outer space.”
  14. “What planet best defines you— the lost and cold Pluto or the diamond Jupiter? 
  15. “What animal best defines you?”
  16. “On a scale of 1-10, how dumb do you think humans are?”
  17. “Rate your intelligence on a scale of 1-10.”
  18. “If you had to execute a robbery, how would you do it?”
  19. “What was worse— money heist or Peaky blinders?”
  20. “Slow dance or drunk dance?” 
  21. Do you think I can be the next president?”

Random conversations without a direction may also help you lead the way to his heart; you never know. In fact, random questions are considered one of the best conversation starters. Collect all your random thoughts and questions and swiftly slide them into your crush’s inbox. 

  1. “Whenever I’m drunk, I always pretend to fly. Do you think I can fly, too?”
  2. “If I could fly, I would have taken you for a great ride. Would you mind joining me?” 
  3. “I had a weird morning dream today. It was horrifying, filled with ghosts, eariness, and silence. Somebody kept following me, and I ran and ran. When I reached home, I couldn’t get inside. The mysterious ghost was so close to me that I could feel him behind me. I found its fingers on my back, and then I woke up. I had goosebumps and sweat all over my body when I woke up. Do you think ghosts are real?”
  4. “Would you go to a haunted house alone?”
  5. “Do you believe in ghosts, evils, and god?”
  6. “Do you think black magic exists?” 
  7. “Did your speedo ever get stuck in your ass in public?” How did you get out of it? Lmao. 
  8. “Who do you think are more intelligent— girls or boys?”
  9. “On a dark rainy day, what would you do— would you sit inside and watch the rain or go outside and get drenched?”
  10. “Morning or night?” 

It doesn’t only have to be questions. Send him over your weird, random thoughts, too. He would absolutely admire you for being bold and open and will also respond with the same enthusiasm. 

How to start a convo with a guy? Give and take recommendations.

Individuals love to give suggestions, life lessons, and recommendations— sharing our wisdom is human essence. Use this opportunity to offer a fine collection of your taste and knowledge. Simultaneously, ask for his recommendations, and you may spark a beautiful conversation on the go. 

  • Share music, art, books, novels, poetry, and random facts.
  • You can ask him for a good restaurant, a serene library, an excellent place to visit, movies, series, youtube vlogs, etc. 

There are limitless suggestions to take and give, trust me! 

  1. “You might like this book; the genre is philosophy.” (The storm by Khalil Gibran) 
  2. “Listen to this masterpiece; you will be damned.” (Thunderstruck by 2cellos)
  3. “This series will explode your brain.” (Dark, the german series by Baran DDo Odar and Jantje Friese.)

Once they go through your recommendations— a detailed discussion is undoubtedly on your way, especially if you recommend the series Dark. Its story will make him lose his mind. Recommend, sit back, and smile when he returns bewildered. 

Use Social Media in your favor. 

Thanks to social media, you have endless means to contact a guy and start a conversation without ever saying much in return. There’s Snapchat, Instagram, and of course, Twitter (For our highly opinionated doodles) 

social media usage strong

Starting a conversation has become as easy as sending a meme or a snap. So, why lose the opportunity? 

Send a meme, and let the fun begin. 

Presently, literally, everyone enjoys sharing and receiving memes. It’s hilarious and stimulating. If you both share a similar sense of humor, the trail of messages may never end! 

Send a snap and continue the streak. 

Snapchat is a unique social media platform— it allows you to communicate through pictures. You can send a photo of yourself, a picture of your surroundings, your pet, the party you are at, or anything around you worth clicking— and the streak will begin. 

Leave comments on his profile.

Compliment him on his recent photo or ask about the location of his current travel voyage. Individuals may or may not look at their inboxes but often reply to comments. 

So, be genuine and crafty when leaving a comment;

  1. “Love the way you smile.”
  2. “Those dance moves are sleek.”
  3. “Where is this place? It looks great!” 

Reply to his stories/snap.

Engage with him on social media! Don’t play the pretend game and leave his stories unnoticed. You must show genuine interest in his life and not allow ego to stop you from trying. 

Please know, replying to his stories isn’t a desperate move; it shows interest! 

What to talk about with a guy? Talk about his interests.

Showing genuine interest in his life will naturally attract your boy crush towards you. Plus, he would actually enjoy talking about his passion.

  • Ask him about his pet(s). 
  • Passionately talk about his passion, whatever it may be. He can be a rookie musician, a part-time magician, someone with great handwriting, someone who creates art, his selection in food, music etc., etc. 
  • Pay attention to the details he tells you. You remembering them will bloom his heart. 
  • Be aware of his emotions and ask about his health and whereabouts. (Don’t cross the boundaries, though.)
  • Be compassionate and appreciative. 
  • If he has tattoos, ask about the story behind them. 
  • Be curious about his childhood.

Simple and straightforward is good, infact, excellent. 

Use the environment around you— every corner has a story to reveal and a conversation to start. The cloudy weather around you or perhaps the indoor plant that doesn’t want to live. It can be literally anything. 

  1. “The weather is nostalgic, isn’t it?
  2. “My day was surprisingly hilarious; how was yours? I hope you didn’t spill coffee over your customer like me. 
  3. “My coffee is awful. Do you have a better cafe to recommend?”
  4. “What should I eat today?”
  5. “Do you want to have ramen? I know a great place. (If you know, you know)
  6. “Do you like sushi?”
  7. “What’s your go-to food?” 

Your conversations don’t always need to include serious discussions; they can be as breezy and as light-weighted. You can rant about your daily mishaps for all anybody cares, and it would still be fun! 

Go old-school

Introduce yourself like the good-old millennial you are! Old-school doesn’t limit to millennials— don’t stop yourself from taking the chance. 

  1. “Hi, I’m Laila. We met at the library. Your book suggestions were great! Can we meet again over a cup of tea for some more novel revelations?”
  1. “Hi there, we exchanged numbers at the puppy cafe near Busan. Just here to talk to you again.” 

Use an inside joke or reference the previous encounter. 

Have you shared silly jokes and moments with your boy crush when you first met him? Use it to break the ice. 

  1. “Your coffee spill was epic! Did you get the stain off your shirt?”
  2. “How’s the ass? I mean, you fell hysterically when we first met; I was concerned.” *add wink*
  3. “It was totally your fault why we were thrown out of that library. I wasn’t the one laughing out loud; you were!” 
  4. “Joe told me you had an interview— how’s the new company?” 
  5. “That book you recommended was lit! I still have goosebumps!”
  6. “Oh my god! Jonas is actually Adam!?” (Reference to the German series Dark) 

Even if you have the most minor history with this certain guy, use it! He wouldn’t mind talking to someone he’s already met! 

Good-old memories never die.

  1. “I can’t believe you are the same guy I kicked in high school. My apologies!”
  2. “You are still cute to me. I don’t know why girls find you intimidating.”
  3. “You have grown beautifully. I see abs. I call dibs.” 

If you both share a history together, things will get easier for you. 

Talk about mutual friends.

  1. “I can’t believe you are friends with Michael. Here I thought we were into sane people. Miserably wrong at that”
  1. “Martha tells me you go to the same gym. We should definitely work out together!.”

Being friends with his friends directly gains you his trust and kinship, especially if that friend is his best friend. Discuss and reference your friend to grab his attention. 

How to build confidence to talk to your crush?

“Remember, Rejection isn’t the end game.” 

If you think there’s not a human who has ever been rejected, think again! Rejection is a crucial part of our lives— it redirects us to something better, something worth our time. 

There are going to be men who may not find you interesting enough, but it’s also sure that there are men who will love your very existence. So, accept rejection and move on to the next sexy man you come across. 

There are only 3.9 billion men on earth— a few rejections may help you find the best one amongst them. Trust me, even the most charismatic people get rejected, not once, twice, or thrice— but more than a hundred times. 

The fear of rejection will never allow you to attempt; it may also make you lose a chance at a beautiful relationship. So, take the first step! 

“Rejection is always better than regret.” 

“Their Judgment doesn’t define you.”

Judgment often stems from one’s own shortcomings. They judge you because they cannot judge themselves. 

girl reflecting

“It’s not you… it’s them.” As mainstream as it may sound, their judgment circles around their own perspective, not yours. Let the world be; at least, don’t judge yourself. You are beautiful, charismatic, sexy, intelligent, and unique in your own ways— find your values. 

Develop a sense of worthiness and know any man would be blessed to have you! 

  • Continue to grow as a person
  • Learn from your past relationships
  • Recall your personality and make changes that seem suitable for you (not for them) 
  • Take criticism with a positive attitude. 
  • Don’t allow judgment to get to you. 

Instead of fearing judgment, invest energy in rebuilding and rediscovering yourself. 

Don’t overthink about texting him.

Texting first isn’t a crime! While calling after certain hours (midnight) should be illegal, the same is not the case with texting. You can text at any hour, and it won’t disturb the receiver much unless you decide to bombard them with multiple messages. 

They will reply to you when ready/available/accessible. I consider texting during non-office hours quite romantic. For instance, when you receive a text at midnight— there’s a different aura and feel behind that same message. 

  1. “The moon is beautiful at this hour. Are you looking at it, too?”
  2. “This night reminds me of our first encounter. It’s just as breezy and pretty as it was that night.”
  3. “Midnight is the perfect hour to start a calm conversation, care to join me?” 
  4. “I’m most definitely a nyctophile, what about you? Do you like the starry sky too, calm and vivid? Please, don’t tell me you prefer the Sun over the moon! 

Do’s and don’ts of texting.

  • Don’t constantly text, especially when he’s not available online. 
  • Allow him space to get back to you if he has mentioned so. 
  • Don’t hesitate to check up on him if you think something’s wrong. 
  • Don’t jump to conclusions if he doesn’t reply to you immediately.
  • Don’t talk about stuff that he isn’t enthusiastic about.
  • Allow the conversation to be a combination of questions, answers, discussions, teasing, and flirting.
  • Don’t ask too many questions continuously. Allow every conversation to flow smoothly and then jump to the next question. 
  • Allow the conversation to be light and fun initially. Don’t inflict heavy topics in the start. 
  • Don’t just talk about yourself, but be attentive and curious to listen to him. 
  • Learn texting red flags. 

Learn if he’s interested in you or doesn’t want a relationship at the moment here. 

Wrapping up

“You don’t have to see the whole staircase, just take the first step.”

The initial restlessness is worth every sweat once you receive your crush’s much-awaited reply. However, don’t burn yourself down with anxiety and overthinking. 

No matter how dreadful the situation may seem given all the overthinking— it’s not a life or death situation. It’s not even a percent of what you are making it to be— so breathe and take the first step, the rest will be history. 

by Genesis Gutierrez

Genesis is an accomplished entrepreneur, advocate, and coach who has dedicated her career to empowering women around the world. As the CEO of Harness Magazine, a digital media company, she has grown a platform that celebrates and amplifies the voices of women from all walks of life.

A first-generation college graduate with a degree from UCLA and growing up undocumented, Genesis brings a unique perspective and a deep understanding of the challenges that women face in today's world. Her work as a coach has helped countless women find the courage and confidence to pursue their dreams and achieve their goals.

Driven by a passion for social justice and a commitment to building a more equitable and inclusive society, Genesis has become a respected voice in the women's empowerment movement.

Through her work with Harness Magazine and as a coach, Genesis continues to inspire and empower women to take control of their lives and create a brighter, more hopeful future for themselves and for generations to come.

More From Relationships

Breaking the Cycle – 30 Years Apart

by Maria Beben

Lovers to Friends. Is It Worth It?

by Rebecca Espinoza

I Miss My Ex: Navigating Emotions and Moving Forward

by Genesis Gutierrez


by Anna Cambridge

Mine All Mine

by Lydia Allen

Leave a Reply

Your email address will not be published. Required fields are marked *