Interesting Text Messages to Send to a Guy (With 15+ Intriguing Examples)

As Amazon Associates we earn from qualifying purchases. When you buy through links on our site, we may earn an affiliate commission at no additional cost to you. This post may contain affiliate links. See our disclosure for full info.

Have you ever started texting a guy you like, only to find yourself running out of things to say? Even if conversations flow easily between you two in person, you might struggle to find interesting text messages to send to a guy.

Worst of all, you might find yourself clinging to boring old classics like, “how are you?” There’s nothing better at making a man yawn than flavorless text messages like that!

If you’re looking for a way to be more interesting, then you’re in the right place. We’ve pulled together a list of interesting texts and tips for keeping your man intrigued.

The Anatomy of a Good Text

Let’s start by looking at what you need in order to make the perfect text for him. That way, even if you don’t use any of our examples, you’ll know what it takes to craft the perfect message.

The ideal text should have these elements:

  • More than one word.
  • Not too long.
  • Easygoing tone.
  • Expressiveness without being too emotional.
  • A hint of flirtation.

It has multiple words…

Want to know one of the easiest ways to kill any text conversation? A one-word text. There’s nothing that destroys a mood faster than a cold, impersonal “k” or “sure” message in response to anything.

You probably don’t know how to answer a text like that gracefully, so don’t assume the guy you like does, either. Give him something to reply to, whether it’s an emoji or a couple extra words for some more details.

Here’s what NOT to do:

Him: Want to see a movie with me this weekend?

You: K

Here’s what you should do:

Him: Want to see a movie with me this weekend?

You: Sure, that sounds great! Which one were you thinking of?

…but it’s not too long.

"You shouldn’t use only one word when you answer him, but you also shouldn’t flood him with details, either."

Related Article: How to Reply to One-Word Texts from Guys (5 Proven Methods)

You shouldn’t use only one word when you answer him, but you also shouldn’t flood him with details, either. Texting is a delicate balance.

Ideally, your text message should be one or two sentences. Sending him whole paragraphs or more should be reserved for when you’re telling him a story, or the conversation demands more detail.

If you’re wondering why that is, consider how annoying it is to scroll through paragraphs of text on your phone’s screen. He’s likely not going to be excited about having to do the same thing on his end of the conversation.

Here’s what NOT to do:

Him: How was your day?

You: It was super boring. I just got out of bed, had a smoothie for breakfast, then went to work. I had a meeting that honestly probably could have been sent in an email, and I didn’t get to take my lunch break because I was so busy afterwards. The commute back home was unusually short, though, so now I have time to make a nice dinner.

Here’s what you should do:

Him: How was your day?

You: It was great, thanks for asking! What about yours?

The tone is easygoing.

It’s okay to be upset or feel under the weather. We can’t always help the way we feel. However, unless you know the guy well, try to keep such sentiments out of your talks with him.

Tell him about your negative feelings constantly, and you run the risk of him just thinking you’re too depressing to talk to. Nobody likes to talk to Debbie Downers or Negative Nancys, so keep this in mind when you answer him.

Instead, your tone should be easygoing and light as possible. This makes it simpler for him to respond.

Side Note: Check out our ultimate guide on sending texts to guys.

VIDEO REVEALS: Secret 'Desire' text message that men are powerless to resist

Here’s what NOT to do:

Him: How was your day?

You: It was awful! First, I had to walk to work in the stupid rain. Then my boss had a boring meeting that honestly should have just been an email. I had to skip my lunchbreak because I was so busy after the meeting. Now I’m eating some horrible old leftovers for dinner.

Here’s what you should do:

Him: How was your day?

You: I’ve had worse – but I’ve also had better! How about your day?

You Might Also Like: Random Things to Text a Guy You Like (That He Won't Be Able to Resist)

It’s expressive without being excessive.

"It’s important that the conversation is light and friendly, but you also need to stop yourself from being bland."

This kind of ties in with the above part about keeping your tone easygoing. It’s important that the conversation is light and friendly, but you also need to stop yourself from being bland.

You’re not a robot. Sure, you can fake a perfectly even, friendly tone all the time, but that wouldn’t be you, would it?

Splash some of your personality into your texts. Sprinkle some sarcasm in if that’s your cup of tea, or throw in some cute sentiments if you’re in the mood. Just avoid becoming overly emotional or spilling your guts to him – you might just make him feel like he’s under pressure.

Here’s what NOT to do:

Him: How are you feeling today?

You: Well, you just texted me, so I’d say I’m feeling pretty in love now. <3 Your text messages always make me feel so happy. I’ve been thinking of you all day.

Here’s what you should do:

Him: How are you feeling today?

You: Now that you’ve texted me? Pretty good, I’d say. ? How about you?

There’s just a hint of flirtation.

"Just like fine spices, you shouldn’t dump too much flirtation into your messages."

More likely than not, you’re talking to the guy in the first place because you like him. You probably wouldn’t have exchanged numbers with him otherwise.

To keep his interest, make sure you’re stirring in a hint of flirtation to texts you send him regularly. This will show him you’re interested, and if he feels the same way, it will keep him intrigued by your conversations and where they might go.

The problem with this is you need to do it delicately. Just like fine spices, you shouldn’t dump too much flirtation into your messages. If you’re too obvious constantly, he’ll start to think you’re desperate.

The previous example is a good demonstration of sprinkling just a bit of flirtation in. A wink face always clears up your tone and shows him what you mean.

Need some more help writing flirty messages? You can find some helpful text templates in the Text Chemistry course. It was written by a relationship coach named Amy North who excels in teaching women how to write sizzling texts that have any guy hoping for more.

Interesting Text Messages to Send to a Guy

Appeal to his base nature by sending him something dirty.

"There’s no getting around it: men are generally motivated by the physical aspect of relationships."

There’s no getting around it: men are generally motivated by the physical aspect of relationships. This isn’t necessarily true for all of them, of course, but it’s true for a large enough number of them that it probably applies to your guy, too.

If you’re feeling comfortable enough, sending him something a little dirty is the perfect way to interest him. It will get his heart pumping and his imagination racing as he pictures exactly what you mean.


  • A tantalizing selfie with a little cleavage or your most flattering outfit. (Bonus points if you ask him to send you a hot pic of his own.)
  • “I couldn’t sleep last night because I kept having the most interesting thoughts about you…”
  • “I just bought some gorgeous new lingerie. Want to come over and see it in person?”

Read Also: 10 Things to Text a Guy to Make Him Blush (That Work Every Time)

Play some texting games.

Games don’t have to just be limited to video games or sports. You can easily transfer the fun to your text messages to keep him invested in the conversation.

Texting games are surprisingly popular and are a fantastic way to get to know each other. Would you rather, for example, is an easy one to play over text.

Twenty questions is, of course, another game you could play. Take turns thinking of something, and then give the other person 20 questions before they have to guess what you’re thinking of.

You could also try asking him some of the most interesting questions you think of. If you get out of the boring favorite food and music territory, you can learn some truly amazing things about a person.


  • “Would you rather eat a ghost pepper or smell a dirty sock?”
  • “What is the food you’re best at cooking?”
  • “If you won the lottery tomorrow, what are the first things you’d do with the money?”

Read Also: 40+ Dirty Things to Dare a Guy Over Text 

Dig into topics he’s interested in.

"Even if you’re not personally interested in all his hobbies at first, you’re likely to find out something that piques your curiosity."

Unless you’ve only just met the guy, you probably know about some things he’s into by now. These are the ideal things to talk about because he already likes them. He also probably loves talking about them.

So if you know about his favorite sport, ask him for trivia about the team he roots for. If you know he’s a gamer, why not ask him what games he would recommend you try?

Even if you’re not personally interested in all his hobbies at first, you’re likely to find out something that piques your curiosity. He’ll also think you’re a great conversationalist, because you’ll have remembered some of his hobbies.


  • “Tell me something weird about *his favorite sports team/band.*”
  • “If you had to recommend one video game to me, which one would you recommend and why?”
  • “What’s one band you like that you think I’ve never heard of?”

Get a bit of competition going.

Guys aren’t just motivated by the physical – they also tend to love competition. Whether it’s ferociously cheering for their favorite teams, debating which bands are better, or dominating in video games, nothing gets their blood pumping quite so much as fighting to win.

You’ll definitely get your guy to perk up a bit when you challenge his competitive nature. If there’s a game in the app store that you can both play on your phones, why not see if you can get a higher score than him?

You could even challenge him to make you laugh, or vice versa. No matter what the competition is, he’ll probably get excited. (There’s an opportunity for bonus points here, too, if you have some kind of stake, such as the loser having to pay for the next date.)


  • “I bet you can’t make me laugh with one picture.”
  • Turn it around: “I bet I can make you laugh with just one text.”
  • “One dinner says you can’t beat my score in this game.”

Read Also: Playful Things to Text a Guy (With 45 Examples You Can Use)

Use your dazzling wit to make him laugh.

Think about your favorite people to hang out with or talk to. A lot of them probably have one thing in common: they can make you smile and laugh. There’s nothing like an afternoon spent clutching your stomach after laughing too hard with your friends, after all.

If you can do the same thing to the man you’re texting, he’s going to remember you. He’ll associate talking to you with having a blast, so he’ll want to talk to you more and more.

Once you get a feel for his humor, use it to your advantage. Text him jokes you know will make him crack a smile.


  • Send him a meme about something he’s into.
  • Find the worst dad joke you can and send it to him.

Tell him a story that will leave him on the edge of his seat.

Are you a good storyteller? Use that to your advantage by spinning a good yarn for him through text. This is one of the few times where it’s totally okay to send him longer messages – but make sure you break it up and weave in a little suspense to reel him in.

Start with a good hook. Then, like our favorite tv shows, stop on a cliffhanger if you can to get him invested. If you’re telling a great story, he’ll be begging you for the ending.


  • “You won’t believe what crazy thing happened to me today…”
  • “My boss called me to her office today. I could have sworn my heart was going to explode in terror when I opened the door and saw the look on her face.”
  • “I saw the weirdest thing while I was out walking my dog this afternoon. I think I might have nightmares about it.”

Read Also: What to Text a Guy to Catch his Attention (Without Seeming Cllingy)  

Don’t be afraid to show off how you look if you’re feeling confident.

Is your outfit on point today? A lot of men are visual creatures – showing him how you look is one way to make him smile or salivate over you.

While you can use this opportunity to be sexy, you certainly don’t have to. You can show him a cute picture of your smile, or a cool one of you in sunglasses.

Whatever your feeling, get creative and capture the mood in your picture. It will undoubtedly catch his attention.

Ask for his guidance on something he cares about.

Nothing flatters a guy as much as being asked for guidance. If you pick something he’s into and ask him how you can do it or parts of it, he’ll feel as if you’re treating him like an expert.

Naturally, he won’t want to let you down. He’ll love to provide you with his expert advice, and he’ll also feel great that you trusted him enough to ask for his opinion.


  • “You told me you were into video games. Can you give me some ideas on what I can play next?”
  • “Would you mind giving me some tips on how to build a character in Dungeons and Dragons?”
  • “I never really learned how to change a tire on my car. Do you have any pointers?”

Further Reading: I Want to Kiss You Texts for Him (With 15 Examples You Can Use)

How to Become the Best Texter He’s Ever Experienced

Texting gets pretty confusing sometimes. A lot of the emotion gets lost in the cold letters on your phone’s screen.

Whether you like it or not, though, texting is likely here to stay. It’s one of the easiest ways to communicate, and until something better comes along, it’s probably going to be the method of choice for many guys.

If you’re feeling really insecure about your texting skills, there are things you can do to become the best texter he’s ever experienced. If it sounds impossible, believe us when we say it’s completely doable.

How? Try tapping into the knowledge of experts. Amy North, a skilled relationship coach, has developed a Text Chemistry program that is built to help women become master texters. With her templates, you’ll have your guy demanding to see you again in no time.