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How to Start a Conversation With a Guy (and How to Keep it Going + 100 Conversation Starters)

How to Start a Conversation With a Guy (and How to Keep it Going + 100 Conversation Starters)

Updated on May 03, 2022 | Published on Mar 17, 2022

Reviewed by Julianne Cantarella, MSW, LSW , Certified Relationship Coach

How to Start a Conversation With a Guy [100 Conversation Starters]

Wondering how to start a conversation with a guy? Always noticed that cute and hot mess, but never approached him? 

Gotta say, good job with the research… because this think-piece will spill all the secrets about starting conversations with him in real life and texts!

Let’s face it… when we see that sexy hunk/cute nerd… both of our palms sweat, butterflies flutter in our stomachs, and our mind becomes a gooey mess.

Well, this think-piece definitely can’t stop the physiological responses… however, you’ll become more confident. You’ll know exactly how to drive conversations and express your emotions.

Curious how? With hopes of successful encounters, let’s begin with…

How to start a conversation with a guy in real life?

Talking to a man in real life isn’t an easy feat. It becomes tougher when you think “Oh My Gosh he’s so out of my league!”

But you don’t really need much to break the ice. In fact, guys are quite simple… if they’re single, your courage can make them fall for you head over heels. 

Wondering how? Follow me, babe…

1. Begin with a confident intro

If you don’t know one another or they don’t know you exist… How will you begin? But hey, someone gotta break the ice why not you?

Whether he’s your bestie’s roommate, a co-worker, or that boy who works in the flower shop… take a deep breath, check your appearance, push back your shoulders, and approach them with a smile.

Don’t smile eerily or say anything like “I always noticed you doing…” that sounds stalkerish. Rather, keep it simple like…

“Hey there, <your name> here, can I get yours? You always caught my eye… so thought we can talk and maybe know each other”

Don’t let awkwardness creep in and try to keep a straightforward attitude. And if they give away their name, that’s a good sign.

2. Take advantage of the surroundings

This is another smooth way to begin a conversation. There is so much happening in your surroundings at all times…

It might be the international breaking news – war, covid, or something more positive like the weather, traffic, or specifically something around you.

For instance, if he’s a barista, ask about the rush hour… if he’s a co-worker, ask about their project (but don’t act like you’re spying on his project).

If you meet him in the supermarket, ask him if he knows about a product. Or, if it’s a ride, talk to yourself about how late you are.

Use indirect hints to break the ice.

3. Ask Superman to help

Let’s be honest, men love playing savior. It’s wired in them and they feel good about themselves. So, how about you boost his confidence today?

If that handsome hunk passes by while you’re carrying heavy things… ask him for help.

Ask them “Excuse me… can you please give me a hand in this”. Usually, men don’t refuse such a plea for help.

However, don’t repeat any trick, else they’ll catch onto you. We don’t want him saying “Oh that one is totally falling for me”.

4. Sneak in compliments wisely

If they do you a favor, don’t forget to thank them. This stereotyping world takes men’s efforts for granted. Men also have insecurities and feel low. A thank you can change their mood within seconds.

If there’s nothing to acknowledge or express gratitude for, hit them with compliments. However, don’t hit a sore spot or make up fake compliments.

Say, “I love how you’re so helping”… only if he helped you or someone else in front of you. Don’t assume something to compliment them.

5. Hit up with questions

If you’re interested in him, show it. If you want to know more about him, ask him. What’s the point of asking your mutual friends if the person is right in front of you?

Ask if they watched last night’s game… or their opinion about the professor. Avoid one-word answers and stick to open-ended questions.

While starting a conversation, never dominate it. Give him more room to speak and express.

6. Target the cozy commons

If you know this guy for a while, better pick the common interest only. To have a good time and keep the conversation flowing, always choose something comfortable for you both.

For instance, you both experienced bad relationships… That is common, but that doesn’t bring joy. Try not to open old wounds, even if it’s common.

So, ask him about a common music band, rugby team, or even an unfamiliar but interesting merch. Express your interests to keep them hooked.

7. Listen to them with your heart

A lot of people talk, but how many listen to you? Can your parents guess your childhood trauma? Can your best friend tell you what you don’t like about them?

A lot of people take you for granted and hardly pay attention. Be a good listener because you need it for a great conversation.

Don’t interrupt them, nod to show you’re focussed, and notice his personality. This also will keep them interested in talking to you.

Remember, there are many great speakers, but very few great listeners.

8. Make it interesting

Ask them random yet interesting questions… something people hardly ever think about. For instance,

“If you become the world’s richest man, what will you do?”

“If you get the power to reverse time, what will you change?”

They’ll think you’re crazy (in a good way) and look forward to talking with you. Open the door to an intellectual and fascinating conversation with you.

It’s a great way to break the awkwardness in your conversations.

9. Pop culture to the rescue!

If you’re ever in doubt, use any show, music, movie, books, or event. If he’s in your friend circle and your other friends discuss anything… ask him if he’s into it.

Don’t assume that he likes it… stereotyping doesn’t help your impression.

However, notice their expression when you speak… assume their mood in your mind. Help yourself to make them comfortable in your presence.

If you find something in common, ask them “Wanna watch/attend the movie/concert together?”

10. Maintain eye contact while you laugh

When they start talking, react appropriately. If it’s a joke, laugh and look them in the eye. If it’s something sad, give them an apologetic expression and again eye contact.

Express your emotions with your eyes. You’ll seem friendlier and it’ll warm them up. Eye contact expresses your confidence and interest in him. However, don’t stare too hard.

Also, he’ll feel good about himself if he can make you laugh. And of course, you look stunning with your smile, so why not?

11. Don’t make it obvious

If you want to take it to the next level, I’m your supporter. But remember, they’re not the only male around. Don’t stick to them too often to make them feel good.

They must put some effort too… as per T-Swift men love the chase. Be mysterious, don’t tell him everything about you, and let him actually make a move on you.

Also, don’t talk about your love life… he’ll know where you’re heading and soon lose interest.

12. Put effort in yourself

Wanna hit on a guy… start a good conversation… or, get his number? Always flaunt your best look, because men are visual beings.

I don’t encourage physical attraction, but it’s important. Always be a good human by nature, be empathetic, intelligent, friendly… but also look good. It’ll set you apart from the crowd.

No need for cakey makeup, slim waist, or fancy nails. Rather, dress appropriately, accentuate your features and keep yourself clean and hygienic.

13. Touch without scaring him

Since you’re meeting face-to-face (FTF), in real life… break the touch barrier.

However there’s a catch… bump shoulders, pat him on the back, gently place your hand over his, or touch his face when he’s down.

But, don’t get too sexual… don’t touch them around their crotch or chest. Apologize and retreat if they flinch. And don’t touch them too frequently either.

14. Sign off when it’s interesting

Once you converse about one interesting or fulfilling topic, step away. Leave it on the interesting phase and he’ll be more eager for the next time.

If you quench his thirst about you today… Why will he ever reach out? So, girl (or boy, no judging), take charge and leave before the exchange turns cold.

And let’s hope he’ll ask for the next meet-up too.

15. Plan the next date

Let’s just say he’s too shy… he didn’t ask you out for the next date. Once again, take charge of the wheels and ask him out.

Say “I had a great time talking with you… it’s a pity I’m out of time. So, wanna catch up again?”

Exchange contact info and settle on your next date. Remember, it’s a friendly date, don’t expect too much out of it.

Wondering how to break the ice IRL? Let’s check these…


50 Conversation Starters for guys (for real life)

Honestly, when you approach that cute guy, you may not remember so many steps. I don’t blame you, our hormones are like that.

Even when guys try to attract women, they’re also stuck with the same rushing adrenaline. Rather than following steps, stick to some basic opening lines. 

Continue with the conversation flow once you begin with one of these…

1. Hey, <your-name> here… can I get yours?

2. It’s really crowded on this train… didn’t see you ever on this route. Are you new here?

3. Recommend me some cheap but good food. I’m really tight on cash…

4. Hey, what’s that book you’re reading? What genre is it?

5. I saw you helped the janitor yesterday. Thanks for making the world a better place.

6. Okay, is it just me, or did you get a fabulous haircut? You look like someone from a fairytale.

7. Hey… this logo on your T-shirt… is it a music band merch?

8. So, I’m really in a pinch, can you help me move in? My friend had an urgency last-minute…

9. The sky is unusually dark today… there wasn’t anything on the forecast. Did you bring an umbrella?

10. Don’t mind me being nosy… I like what you’re reading. Also, give a try to <suggestion>.

11. I’ll go grab a coffee, do you want anything?

12. Hey, I didn’t know you were invited. How do you know the host?

13. I always thought I heard your voice somewhere… You sound a lot like Benedict Cumberbatch.

14. So, what’s the meaning of your tattoo? When did you get it done?

15. My entire week was terrible… How was yours?

16. You tried paragliding, right? Give me some tips… I wanna try but I’m so scared.

17. You think aliens exist?

18. Pick one animal you want to be and why.

19. What’s a must in your dream house?

20. Tell me about your worst wardrobe malfunction.

21. What are you most embarrassed about your teenage self?

22. What did you always want on your birthdays… but never got?

23. What was the best/worst gift you ever got?

24. I want to check out a café, are you up for it?

25. You’re a <designation>? Sounds cool, what are your responsibilities?

26. What did you not understand in the Avengers series?

27. Who are you closest to in your family?

28. When was the happiest day in your workplace?

29. What do you fear the most? Mine’s <your-fear>.

30. What did you plan to become in your childhood?

31. There is so much good food, suggest something worth it!

32. I bet I tried all possible desserts. Recommend me something unique!

33. This place is so cool… When did you know about it?

34. Recommend me your favorite eatery… I’m feeling a bit adventurous.

35. Are you busy these days? You seem so distracted…

36. Did you ever go to <event-name>? I’m a staff member.

37. You look really interesting… a penny for your story?

38. What are you passionate about? Anything you wanna make a business out of?

39. I see you sitting here every day. So, I wanted to befriend you.

40. I know <mutual-friend> is close to you, but I swear I’m closer to them.

41. Your drink seems interesting… What are you having?

42. You were a soccer player back in school? Give me a few tips… My nephew wants to enroll.

43. Tell me something I’ll never guess about you.

44. Are you reaching closer or farther from your dream job? What is it?

45. What do you love the most about this place?

46. If someone pays you for your likes, what will it be?

47. What do you miss the most about your childhood?

48. What can you cook the best? How much do you like it?

49. How many childhood friends did you lose touch with?

50. I really like talking with you… think we can exchange contacts?

So, you have successfully started a conversation but don’t know how to keep going? I think I know what you need. Come on, let’s move to…


How to keep the conversation going with a guy in real life?

Striking a conversation is a lot easier than . In fact, if he’s friendly, you’ll face zero trouble with that. However, that hard part comes next… people hardly know how to be interesting. In fact, many don’t know how to skip between topics. 

Such rough edges make you too transparent to the other person… you can’t afford to lose your mysteriousness, so know how here…

1. Listen to their calm and chaos

You don’t always need to talk. If you’re both having fun silently, that’s cool. Don’t stress on topics, and let him lead. When he feels uncomfortable, he’ll try to strike silly conversations… and that’s cute.

They might blurt out something embarrassing to break the awkward silence. If he talks about something completely alien, tell them you don’t understand but wanna.

If it’s something about their sad past, listen actively and gently caress their hand.

2. Share uncommon interests

Common interests are good conversation starters… but to continue it use the uncommon ones. Talk about what you like individually.

Express yourself with your interests… it’s not an interrogation, so show your real self freely. Also, know about his interests.

If he’s a bibliophile, ask for recommendations. Or, ask how they’ll respond in an interesting movie/book plot.

Use your likes and dislikes to drive the conversation.

3. Pick the hints to avoid sharp topic changes

Sometimes, you’ll face difficulties switching topics. So, use the last topic’s mood. In FTF conversation, you can notice his expressions better.

If he seems sad, say “I feel the hurt in your voice… but let’s look at the positives…” and begin a motivating story.

If he seems happy, “I like that too, but I love…” Notice how you didn’t ignore his thoughts?

4. Blurt out funny childhood stories

If you search your mind but can’t make a smooth transition… stick to randomness and be silly. Say,

“Hey, this is so random… but I just remembered something silly from my childhood.”

It’ll intrigue them, so carry on. It can also be something funny and recent in your friends’ circle. However, if you’re that close, also feel free to share your painful stories.

Emotional conversations help you feel closer and more familiar.

5. Don’t nudge their emotions

If you know about his childhood trauma, don’t jog that. Don’t entangle yourself with traumatic feelings… unless he brings it up himself.

You wanna make good memories with him, so stick to it. It’s good if he shares his touchy past, not you… especially, if you didn’t hear it from him.

Some people are in general pessimistic… so if you are, don’t spread negativity. Support them, if you can’t help but always notice the downside… work on it.

6. Follow-up on interesting topics

Suppose he says “I waited for this game for so long… and they finally launched it!”

Sounds interesting, right? So, let’s take a deeper dive into his interests. If you don’t know much about it, say “Hey, what’s this game about? I wanna try too.”

If you know about it, go all gaga about it.

Also, if he shares an interesting story and suddenly stops… maybe to create suspense… play along! They want to notice your reactions, so give it to them. Ask “Then what?”

7. Reply with questions

When he asks you close-ended questions… don’t stick to one-word answers. Do a boomerang with an open-ended one. For instance,

Him: “What flavor do you want?”

You: “Usually chocolate… but that’s a regular, think you can suggest something to me?”

Or…

Him: “Did you see <his best friend’s name> today?”

You: “Yes/no… but what happened… you don’t usually ask me/you guys usually hang out together”

Sometimes, intrude on their thoughts to engage them. This will make them understand that you’re interested in their life in a good way.

8. Get the OKAY for other communication forms

If you get closer, consider getting his contact info. However, be polite and play it cool. Never say,

“Hey, you know me for so long… It’s high time we exchanged contacts.” – this is demeaning, even if you say it playfully. Rather say,

“I like talking to you… think we can connect virtually?” – here you’re respectful. You gave him a choice and that’s simply sweeter than honey.

9. Don’t depend on virtual contacts

Suppose you got their phone number from them and you got addicted to texting. Let’s be honest, that’s normal, nothing wrong… however, don’t stick to texts alone.

When you can meet in person, do it. Texts can be misleading and result in misunderstandings. So, indulge more in face-to-face conversations. Break up with laziness if you want success.

Also, either ask for his contact number or connect with him on any one social media. Don’t begin a stalking spree on him.

Blowing up his phone through all possible social media at once is a turn-off. Though it’s not, it feels like a privacy invasion.

So, take breaks in between… If you added him on Facebook today, wait two weeks till you connect on Instagram. Take your time, he won’t run away!

10. Relax and keep relationship labels off

Don’t overwhelm yourself or him during conversations. Even if you connect via all communication forms, don’t feel too excited about it. Don’t DM on all platforms together… unless they do it.

And lastly, if he shows extreme interest in you, don’t assume you’re special. Men make best friends too. So, unless you’re super sure or he tells you about his feelings… you’re friends.

At the same time, if you’re not looking for anything casual, don’t have sex unless he commits.

Thinking about texting him? I’m cheering for you! But before you make a move, know more from…


How to start a conversation with a guy on text?

Texting seems easy because you don’t face him directly… However, that’s where most slip-ups happen. In fact, people slack off in texts… be it with a Tinder date or a best friend. Also, you can’t hear the other person’s emotions.

So, there are so many doors for misunderstandings to sneak in. So, before you tap on the SEND, check these…

1. Add them to your contacts

And you’re like… “Of course I did… that’s why I’m here”. Cool, but did he give you his contact info himself? Or did you get it from a friend?

Don’t text him randomly if he didn’t share it himself. Else, they’ll label you a stalker.

If you know him, ask him his contact number directly during an FTF conversation. Don’t be nervous and go with the flow. Say “Hey, wanna exchange contacts?”

Suppose it’s a stranger, say “I find you really cute and my type… can I get your digits?” Since the other person doesn’t know you better get your intentions clear.

If you met him on a dating site, text on dating apps or ask for his number.

2. Plan for the first text

What’s the most overused yet useless text of all time? “Hi”… yup, it gets you nowhere, sounds boring business-like, and leads to disappointments.

Put yourself in their shoes… you’ll wonder “Ugh… wonder what she wants…”

So, make your needs clear. If you wanna compliment him on his basketball performance, add that with your texts. If it’s about a common interest, keep the text chill.

For random hit-ups, say “Hey, you busy? I was just watching…” You don’t wanna intrude during the wrong hours, so be frank about it.

Also, approach him as a friend… not a suitor. He won’t run away then.

3. Take the cue for the next one

If he’s not busy and near his phone, he’ll reply. So, find your reply in theirs… For instance, he replies “Man, there’s so much work to do…”

Prepare with a follow-up question. If you’re aware of the topic, don’t play innocent. Reply “I know… too much homework/responsibilities…”

If you’re unaware, ask them “What’s up? Am I texting at the wrong time? Can I help in any way?”

Show him you care and you’re generous. Sometimes, people can’t be straightforward even when they’re busy. It hurts their life, but they can’t say no. Help him with your kindness.

4. Notice their tone

When they reply, read the mood… I know it’s hard but that’s how pen pals work. Gotta read in between the lines… and try not to misunderstand them.

If their texts are short, they’re really busy but try not to be too rude. Say “Okay, then we’ll catch up later. Keep up the hard work!” Don’t make yourself look desperate, ‘kay?

If they ask for your help, that’s great too. However, if they ask about you… that’s your queue to continue.

5. Don’t blow your bills

If you’re really into them… you can’t stop texting. However, that’s not a good excuse to exhaust your phone plan.

Get an unlimited text plan for long-hour text conversations. Or, connect online if you have proper internet plans.

If you’re not independent, i.e., depend on your parents for your phone plans… don’t demand more money to text. They already give you enough, so understand them too.

Exchange bare minimum text messages, if you can’t afford a better plan. Don’t shock your caregiver with an enormous bill.

6. No multiple texts either

Forget about multiple texting, if it’s not an emergency, never text more than once. Wait for him to reply to your texts, else you’ll seem desperate.

Multiple texts give away the wrong vibes. He’ll think you don’t have anything better to do. Or, even worse… he’ll think you’re hitting on him and boast about it to his friends.

He might think you want him to commit… men run from those. Text him the way men text men… you know short and single texts.

7. Don’t use abbreviations

Be friendly but don’t slack on respect. “Wen sm1 txts” this way, what do you think?  Sometimes, it becomes hard to understand the texts. You assume they’re lazy and not interested.

If you do the same, this guy might think the same… so abbreviations are no go. However, if you’re both into it… it may work out.

Infact, I’ll still suggest practicing normal typing rather than abbreviations. It’ll help you in the long run during any online dating conversation.

8. Hold back on emojis and stickers

Social media and modern texting apps are great. They allow you colorful emojis, gifs, stickers, and so much more.

However, cut back on excessive usage. Even during light-hearted conversations, use at most 2 smiley emojis.

Unless you’re in a relationship, they flirt, or you guys like one another, don’t use hearts, kisses, or winks. If you’re not serious, that’s misleading. If they don’t have feelings, they’ll ghost you.

Skip the risky emojis to avoid tough situations.

9. Don’t text when you’re busy

This is a given… If you don’t have time, why even hit him up? If you’re busy, you won’t have time to reply.

Without a reply, he’ll conclude a few things: You play hard to get, you’re bossy, you wanna see him follow you around. In short, you may ruin your impression.

Suppose someone matches you online… wait until you have time for text conversations.

If you leave them immediately after starting the conversation, he’ll lose interest and look for another match.

10. Don’t be too eager

Don’t blow his phone all the time. Else, he might think you don’t have a life and are desperate. For instance, a text during the weekends implies you don’t have a happening life.

A text during work hours on weekdays implies you don’t have a job or studies. So, your prime time is after-work hours during weekdays.

11. Text him in good time

If you guys know one another’s schedule, then put it to good use. Know when he wakes up? Do you wake around the same time? Send him a “Good morning” or “Have a nice day”.

Text him “How was your day?” when he returns home or gets off work. He’ll understand that you’re thinking about him. However, you’re not clingy because you let him have the remaining time.

Before you go to sleep, even if he works a night shift… send a “Good night” and/or “Work hard” text.

12. Suggest calling

If you both become comfortable texting, suggest a normal or video call. Texts are great, but how much will you know about a person with typed words?

Also, if you never heard his voice, enjoy the thrill with a call. When you’re both not busy, text him

“Hey, I’m free right now… but too lazy to type. Think we can video call?”

Don’t pressure him into it, allow him to choose for himself.

13. Show off your busy life

Men like anything unattainable so make yourself that. Wanna show off you’re good without them? Well, if you met on a dating site or are connected online, great news!

Post your thrilling weekend pictures.

Don’t reply to them all the time. Some of you misuse this idea, so just in case, I’ll elaborate.

If you begin texting, they reply to you instantly… with all due respect don’t be an a$$hole who replies hours later.

However, if you get late replies, you may return the favor. But make sure to ask them if they’re busy in general to avoid misunderstandings.

14. Crack jokes carefully

Be choosy about jokes and your timing. If they don’t seem jolly, abort the plan. If they’re having fun, and you have a light-hearted conversation, go ahead.

Also, don’t joke about possible emotional places. For instance, if he lost his mom in childhood… your rambles about your mom being nosy won’t sit well with him.

If he’s from a financially weaker family, don’t ask him if he has plans on the weekend. He can have fun without splurging… but it may hurt him.

15. Never rush your replies

Always, think twice before you reply. Take time to understand the text subject. For instance, if he asks “Hey, did you do Mr. Robinsons’ homework?” The subject is homework… not Mr. Robinson.

Say “Oh I totally forgot about it. Thanks for reminding me…what about you?”

Don’t say “Oh Mr. Robinsons gave homework? I forgot it, who cares?”

If he’s serious about something, don’t joke about it even by mistake. Rather spill the truth and ask him for help… It’ll boost his confidence.

Wondering how to strike a conversation via texts? Let’s know it here…


50 Conversation starters for guys (for texts)

Though it’s hard to understand their texts, opening a text convo is rather easy. In fact, it totally depends on your mood, what you’re doing, and how you’re feeling. However, we all become fools in front of that guy, so let’s still check these…

1. What are your plans for the weekend?

2. Lately I’m so stressed… Suggest me some stress-relieving activities.

3. What’s your favorite spot at home?

4. Hey… where’s this place in your story? The scenery is amazing!

5. Didn’t know you were a guitarist… When did you begin? Who was your mentor?

6. Something great happened today… I can’t stop talking about it. Are you free now?

7. Do you know what happened between that couple? They were fine till yesterday…

8. How was your weekend? I’m so eager about that site!

9. How is your mother doing? Any updates? Really hope she’s getting better.

10. You always share memes… and now look at my feed *send a screenshot of your meme-full feed*

11. Hey <his-name>, what do you think about last night’s match? I need to discuss this so badly!

12. Did you watch <show-name>? Try it, I swear it’s so great!

13. Will you feel awkward telling me your zodiac sign?

14. How did you meet your childhood bestie?

15. Ever gone to a music concert? Who was it?

16. Anything you wanna tell your younger self?

17. Hey, I watched this crazy YouTube video, you gotta check it! Tell me what you think!

18. What’s the best thing about today for you?

19. Suggest me some interesting books… I really can’t figure it out.

20. Name a few qualities of your role model.

21. Ten years back, what did you think about your future?

22. Describe your good and bad parts with three words each.

23. Name five things I’ll always find in you.

24. What makes you scream internally or IRL? Hope it’s not my texts 😉

25. Currently, what’s the most exciting thing in your life?

26. What show/book did you recently complete?

27. Tell me something you regularly do before bed.

28. Describe your childhood self in five words.

29. How did you perform in high school?

30. If you get a chance, what will you change about your life?

31. If you were to live off your innate talents, what would it be?

32. I saw a cute poodle today. It reminded me of your dog, send me his picture!

33. How was the presentation/interview/exam?

34. If you can kill an ice cream flavor, what is it?

35. I’m in a huge pinch… Can you help me choose between these outfits?

36. Tell me about your pet peeve.

37. Honestly, tell me what you first thought of me?

38. Which emoji do you use the most?

39. How frequently do you watch your favorite movie?

40. If I got you the ticket to any place right now, what’s it be?

41. Ahh… I gotta say, you look dashing in that suit!

42. I had a really bad day, wanna cheer me up?

43. I can’t believe what I saw in the meeting room. Meet me during lunch break!

44. Is my mind a treadmill for you? Thanks for running in my mind all day long.

45. I bet your regular will ask for your number today. Be ready to be hit on boi!

46. My friend ditched me for Avengers: End Game… wanna fill up?

47. You’re hotter than my phone when I play PubG

48. I hate Autocorrect… it always changes your name into darling.

49. Describe me in five words.

50. So, I was wondering, if you wanna meet up this weekend?

Started texting a guy but the conversation turned cold? Let’s know how to fight that here…


How to keep the conversation going with a guy on text?

Sometimes texts become boring… possibly because you don’t pick the right topics… or he doesn’t understand you well. So, always go for the easier topics. Minimize any chances of misunderstandings, magnify his interest, and continue with a smooth convo with these…

1. Share some life stories

Everyone asks questions to stretch conversations… But do you feel good about it? Think you’ll like it when someone interviews you day in and out about your favorites and interests?

It’s not an interview, so ask open-ended questions. Let him share his life deets for your answers. For instance, ask “What kinda child were you?”

He’ll definitely share something interesting. If he was a naughty one, share your own life incidents. Connect with him with your goofy past. While you’re at it, you’ll naturally know their interests.

2. Compliment his choices

If he tells you about a sad incident… listen to him mindfully. Does he blame himself or his surroundings for it? Or is he happy about it? Whichever it is, pay him a genuine compliment. Tell him…

“Even if you’re unhappy about your choices, you did your best. I can’t imagine dealing with such situations. You inspire me beyond words.”

Everyone will praise his looks and attire… look through his heart to stand out from the crowd.

3. Flirt like a boss

If you feel comfortable, flirt with him low key. Whenever you deck up for a party, send a snap. Make sure you put on light makeup, flaunt your locks, and face the light before taking pictures. Ask him…

“Hey <his-name>, do I look okay? I have an important outing today.”

Well, that might spike a bit of jealousy if he’s into you. If he compliments you, that’s cool. But if he asks you who you’ll meet… he’s hooked!

Also, mentioning his name will grab their attention. But, don’t use it too regularly lest the magic fades.

4. Talk about his pet

Want to win a guy’s heart? If he has a pet, bring them up. If a guy has a pet, he’s a complete softie to them. It’s the shortest way to bond with him.

If he posts pictures with them, talk about it. Text “Awww you’re so cute~”

It’ll catch him off-guard, so when he checks the text, replies “That was for <insert-pet’s-name>, not you! You don’t hold a candle to them.”

Imagine a guy being jealous of his pet… cute, right?

5. Let him know you’re thinking about him

Do this only when you become familiar and close. If you’re not close, he’ll take it as a sign of clinginess. So, refrain from it… however, if you both joke quite a lot, you’re good to go.

Say, “Hey freeloader… thanks for taking up space in my head like that”.

It’s a cute way to hint at your feelings. And he WILL ask about your thoughts. Then reply with…

“My thoughts? Why don’t you imagine it yourself? 😉

Make them want to meet you in person with your cuteness.

6. Tease with a competition

Men are competitive too, they easily give in to provocation. However, when it’s from a beauty, they become even wilder. Respectfully make fun of them and prepare to be made fun of, too.

For instance, if he shares his childhood picture, text “I bet I was cuter than you” Wait for the moment he asks you to send your pictures.

Or, “Are you sure you can handle a gaming bar? I’m the king/queen of many games… I don’t think you can beat me”

Tease him with provocative texts so he’ll want to meet you. Men like solving mysteries… let him solve you now.

7. Share your intentions right

During the weekends, if you go out somewhere cool, get good scenic pictures. Send him private snaps with cool captions.

If it’s a red sunset and you’re serious about him, caption it with “I wish to kiss in this scenery someday… Isn’t it so romantic?”

If you went for a friends’ sleepover, caption a group picture “These are my soulmates… wanna join?”

You’re investing enough time in this person… so you’ll obviously expect something. Don’t keep mum when it’s not new anymore.

8. Know about his day

Just as you want to make sure about his feelings… he needs to know he’s in good hands too. You can’t expect their attention, without showing empathy.

Ask him about his day and empathize with him on bad days. Don’t ask him “How was your day?” on a loop. Mix it up with something new every day.

For instance, some days, talk about your day first and ask “I wonder if either of us had a better day?”

Or, if you know about their presentation, text after work “Hey, how did it all go?”

9. Add suspense to your texts

When you talk about something interesting, create suspense.  For instance, you dreamt of him. Don’t be too straightforward, say…

“I had a great dream while I dozed in class/work. Guess what!”

This will catch him off-guard if you usually don’t make cliffhangers. When they give up, reply…

“Since you failed to guess, there’s a penalty for you! Well, it was about you… and your penalty is meeting me.”

Now, wait for his reply!

10. Go with the flow

If you feel it’s time to meet IRL, text them about it: “Wanna meet this Saturday afternoon? I got tickets to that movie but my bestie can’t make it 😫 Play the damsel in distress wisely.

Sometimes his texts may seem unenthusiastic, give them some space. Don’t coerce them into a plan forcefully. Wait for when he feels comfortable.

A word from ThePleasantRelationship

Whether you start a conversation with a guy in the real world or virtually, approach him as a friend. 

Don’t begin a sexual conversation before communicating about your relationship status or labels. Ensure that you don’t sell yourself short to grab their attention.

Lastly, sometimes conversations don’t work out. If he doesn’t respond to your texts, calls, or in-person convo enthusiastically, it’s not your fault. Let them be and don’t feel sad, perhaps he’s too tired.

However, if you’re sure he isn’t interested, it’s okay. There’s plenty of fish in the sea… and you’re the prettiest of them all. Keep trying, you’ll soon find the right person.

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