how to start a conversation with a guy over text

Do you want to get to know someone, but you are feeling a little shy? A guy doesn’t have to be the one to text you first! Whether it’s someone you just matched with on a dating app, or it’s a crush you’ve had for a while, these tips on how to start a conversation with a guy will help you break the ice.

1. Use the details he’s shared

When you are trying to get to know the guy you like, take note of his interests and hobbies. If you met him online, pay attention to what he wrote in his bio and go from there. Find something that catches your eye and helps you start a meaningful conversation.

Some guys don’t even bother writing anything in their dating profile, or they put only basic information. For example, what are you gonna do with a match whose bio only says “5’7”? So, look for matches with interesting details in their bio.

I love when guys use the “two truths and a lie” prompt, so it’s easy for me to start the chat by guessing which detail was the lie.

Take a look at his hobbies. For example, if a guy likes hiking, you can ask him about his favorite hiking trail.

It’s always easier to start a conversation with someone online when they put effort into their bio. However, it’s up to you to make the first move and be creative about your opening line.

When you are trying to get to know the guy you like, take note of his interests and hobbies. Click To Tweet

2. Be creative with pick-up lines

Flirty pick-up lines can be great conversation starters. No, I’m not talking about lines like “Did it hurt when you fell from heaven?”. Instead, I’m talking about funny pick-up lines that will give you a solid first impression. It’s an excellent alternative for the usual “Hey, how’s it going?”.

Some pick-up lines can be really cheesy and outdated, so you got to be creative with this one. It’s okay to Google some funny and witty pick-up lines, or you can come up with your own. Some examples, and my personal favorites, are:

There’s something wrong with my phone. It doesn’t have your number in it.

Where did you get that shirt? Looks like it’s made of boyfriend material.

When you use creativity in your opening message, most likely, it will make him smile, and he will be intrigued to get to know you.

3. Send a meme

Sending memes is a great way to start a conversation with a guy over text. Make sure to send him things that are relevant to his interests. For instance, if he’s into soccer, send him a meme about the latest match of his favorite team. Or send him a Youtube video of Vine compilations you find funny.

You can even try a meme trend you see on TikTok, like Break My Stride. You send him song lyrics and wait for his reaction. If he’s not in the loop with the meme, it’ll keep him guessing, and he’ll want to keep texting you to get answers.

Sending memes also lets him know that you have a sense of humor, and guys usually love girls who can make them laugh. When you send a text about something that resonates with a guy right away, it’ll signal to him that talking and spending time with you should be fun.

4. Find common ground

young couple outdoors laughing

One thing that can guarantee a reply from the boy you matched with or your crush is texting him something about a common interest. Find common ground and use that to kickstart the conversation.

If you match with a person who has pictures from different countries, see if you’ve been to any of those locations. For example, you can say: “You lived in France? That’s cool! Paris is my favorite city to visit!”

If you both have the same favorite TV show, you can say something along the lines: “Favorite episode of Friends of all time. Go.”

Asking questions about your shared interests will definitely keep the conversation going with a guy.

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5. Keep it lighthearted

When starting a conversation with a guy over text, try to keep it lighthearted. Go with the flow and don’t force it. If you want to have a serious conversation, it is best to wait for the right moment and talk on the phone or when you meet in person.

If you notice that the conversation is stagnating, don’t try to force it by messaging a guy, “You haven’t been texting as much. Did I do something wrong?” Chances are, this will put him off. So instead, try to rephrase it positively. For example: “Hey! I haven’t heard from you in a while. How have you been?”. Or: “I remember you were a bit stressed about the upcoming exam. How did it go?”.

Paying attention to your tone and how you phrase your questions will make the guy you’re crushing on feel welcomed, and texting you back won’t seem like a chore. Instead of replying to you out of courtesy, he’ll look forward to telling you what’s been happening in his life.

When starting a conversation with a guy over text, try to keep it lighthearted. Go with the flow and don't force it. Click To Tweet

6. Let him know you’re thinking of him

Don’t be afraid to be vulnerable when you’re texting the guy you have a crush on. It can be hard to open up and let the other person know that you like him to avoid getting hurt. However, the goal of messaging someone is to get to know him better and develop a relationship.

If you are like me, being vulnerable is actually the key to having meaningful conversations. Tell the guy that you remember all his favorite things, and when you come across those things in your life, they make you think of him. Some examples that you can use are:

I’m watching Star Wars, and it got me thinking of you!

I heard The Weeknd at the mall today, and I thought of you!

The fact that you’ve started to think about him even when you’re not messaging each other will make him feel warm and fuzzy.

7. Make him feel important

This tip will be relevant for you if you are already familiar with the guy. At this point, you may already know all of his favorite things that he’s passionate about.

Ask questions that will help you know him better. It will make him feel special when you ask for his opinion or something only he’d know the answer to. For example, you can ask: I’m celebrating my sister’s birthday tomorrow! She loves Japanese food, just like you. Do you have any recommendations for good Japanese restaurants in the area?

You may think you can just Google these answers, but where’s the fun in that? This way, you can initiate a conversation, and you’ll give him a boost of confidence.

8. Address him by his name

laughing guy

Our names hold a lot of power over us. Ever since childhood, we were taught to answer whenever our name is called. It’s one of the most essential elements of our identity.

Using his name in a conversation is the easiest way to get his attention, and it can also let him know how highly you think of him. Some examples you can use are:

Hey (his name)! There’s a new episode of Money Heist that just came out. Wanna have a viewing party?

(His name), you can’t believe what just happened to me today…

If you are unsure how to start a conversation, you can simply send him a text with his name. You can then follow with a question or statement of your choice.

9. Give him compliments

One way to start a conversation with a guy is by giving him compliments. Guys love getting compliments too, so don’t be shy and start sprinkling them into your conversation. Hearing positive things about himself will make him feel good.

The compliment can be as simple as “You have excellent taste in music” to something as deep as “You’re a beautiful person, inside and out.” Make sure you are sincere when you compliment a guy. It will show that you are a genuine person he can open up to.

While compliments are some of the best ways to get guys’ attention over text, make sure not to go over the top. It is best to wait and see if he returns a compliment to you to gauge if the attraction is mutual.

It is best to wait and see if he returns a compliment to you to gauge if the attraction is mutual. Click To Tweet

10. Send flirty messages

Don’t be scared to flirt through your texts and tease him a little bit. Be playful and engage in a little bit of cheeky conversation. It will show him your fun side and maybe hint him at the possibility of being more than just friends.

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You can send the guy a meme featuring a couple and say: This could be us, but you’re too busy watching football. Or: I can’t wait to beat you at poker tonight! Of course, the loser needs to do a forfeit!

Guys love cheeky banter that makes messaging so much more fun. It’ll make him feel like he can talk about anything with you, not just the serious stuff.

11. Keep the conversation interesting

Open-ended questions will get the guy to talk about more things than he would when you ask boring close-ended questions. When you ask him, “Do you like action movies?” or even the classic “How are you?” he can simply answer yes or no, and the conversation will die off before it even starts.

If you keep asking close-ended questions, your conversation can quickly start feeling like an inquisition, especially if the guy doesn’t ask you anything back. So to keep the conversation going, you can ask open-ended questions like:

If you can describe your life in one song, what song would that be?

Do you have any siblings? What was your childhood like with them?

These questions will often bring out more than just short answers, as they have to be explained in more detail. If the guy likes you, he will want to share as much information on his life with you.

12. Share a personal story

young woman sharing her stories via text

Exchanging stories is a simple and easy way to connect with people. They give more depth to the conversation and make the other person relate to you better.

Share some fun or interesting stories about your life: tell about that day when you fell off a treehouse when playing with your niece, or what are your favorite songs to sing in the shower. Anything that will give the guy an idea of who you are on a personal level.

By sharing your stories, you will encourage the guy to open up as well. This will make your conversation much more interesting and will help build a connection.

13. Get him intrigued

Whatever you talk about initially, don’t rush to open up to a guy and share every single detail about your life. Instead, get him interested and wanting to know more about you, but leave some topics and details for your upcoming conversations. While you might have the urge to text him back as soon as you see his message flashing on your phone, try to space out your texts during the day.

This way, whatever you are discussing with him through the messages can continue for days. I usually have a cut-off time at night when I stop replying to text messages. It gives me time to think about my reply, and it helps to build intrigue and anticipation.

For example, don’t reply to his texts after 11 PM and leave it for the next day. This way, you will continue the conversation with a fresher mind and maybe even come up with more creative and engaging replies.

Get him interested and wanting to know more about you, but leave some topics and details for your upcoming conversations. Click To Tweet

14. Have meaningful conversations

I’m not going to lie; texting someone nonstop can be taxing, especially if the conversation is shallow. So when you want to start a conversation, make sure there’s always a point to the discussion.

You can text the guy you’re interested in to check up on him, but you can’t keep on texting the same old “What’s up?” every day. If you want to build a meaningful connection with a person, you can’t rely only on small talk.

Sometimes, it’s okay to take a break from messaging each other and not force the conversation. You can text each other when you really have something to share or update on something exciting.

15. Be genuinely interested

What makes a text conversation captivating is when you are actually interested in talking to the person. If you keep on sending him generic texts, sooner or later, he will end up losing his interest.

Sometimes, we text people just out of the sheer need to interact with somebody. And that often leads to boring conversations that will quickly die off. If you really want to get to know a guy, you have to show that you are genuinely interested in him.

One way of showing your interest is by asking personal questions, from his favorite movie to his biggest pet peeve. Try to understand him as a person. You need to know whether this guy is compatible with you, and you can figure it out even via text.

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16. Avoid double texting

guy laying in bed with a phone

You don’t need to keep on texting all day, every day. Instead, try to be creative about the texts you send. The truth is that sometimes we get caught up in studies, work, and personal matters that may prevent us from texting someone.

Don’t pester him with double texts if the guy you’re interested in is not texting you back right away. You don’t want to come across as being desperate or clingy. Instead, send him a meme or a video that reminded you of him. But after that, wait until he sends a reply to your previous messages.

A double text can be acceptable if you want to change the topic of the conversation or if you have something really important to say. But, to avoid any awkward responses (or even worse – being ghosted), it’s best to give a guy some space.

17. Be creative

When you start a conversation with a guy, you want him to give you more than just one-worded answers. Ideally, you want him to say something comprehensive that you can follow up and elaborate on.

You can keep the conversation going without prodding the guy with endless questions such as “Where did you grow up?” or “What’s your favorite food?”. Instead, try to practice active listening to avoid having an awkward and boring conversation.

Don’t overthink about what to say to a guy. A good conversation is usually natural yet full of meaning.

18. Keep your cool

When you are having a great conversation with a guy, you may end up fixating on his texts. It is great to have someone who pays attention to you but texting with a guy shouldn’t become the center of your world.

If you notice that he doesn’t text you as frequently as before, give him a couple of days to reply. Sometimes, people need some space, and even if he likes you, he may feel that way. You may think, “If he has time to post on Instagram, why can’t he have time to reply to my messages?”.

Don’t panic and wait a bit before texting him again. If the guy is interested in you, he will reply, and you’ll pick up where you left.

It is great to have someone who pays attention to you but texting with a guy shouldn't become the center of your world. Click To Tweet

19. Be confident

One of the most important things when dating guys is confidence. Don’t doubt that you are an interesting person. You have many things to share, and if a guy stops texting you, it has nothing to do with what you said or how you are.

Sometimes, you might feel anxious or overthink about what to say or not say. While a bit of texting anxiety is normal, not hearing back from a guy is not the end of the world. He may have other priorities in his life, or you would not have much to talk with him anyway, and there’s somebody better waiting for you.

Remember to take it one day at a time and try not to force a conversation just for the sake of getting a reply from the guy you’re interested in. A text conversation is just a temporary buffer until you talk to him in person or over the phone.

20. Have fun

For some people, having a conversation over text might be pretty tiring. However, a lot depends on what you make out of it. You can have as little or as much fun as you like, and if you like the person you are texting with, you may as well make it enjoyable.

Don’t overthink how the conversation is going or how it should have gone. Instead, take it easy, go with the flow, and genuinely try to get to know each other. Keep it casual, especially if it’s your first time getting to know a guy over text.

If you start getting the feeling as if sending him a text is a chore, you may want to step back until you feel you are ready to resume the conversation again. Having fun matters the most when you are just starting to get to know someone, so put your best foot forward and enjoy the ride.

Getting a text back from a guy is easy if you know the simple tactics of texting. These tips are going to help you be better at initiating and continuing fun conversations. And who knows, maybe these tips will help you find a boyfriend!

Brenda is relationships and lifestyle writer, coffee enthusiast, and a lover of new experiences. You’ll usually find her in a coffee shop with her laptop and a flat white scribbling down an article or searching for the next travel destination.

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