What to Text a Guy When Conversation Gets Boring

Sometimes, even with the greatest guy, conversation starts to die down.

It doesn’t mean that’s your fault or his fault. It’s just natural to run out of things to say.

Those basic “how are you” texts are fine for getting a conversation started, but what about keeping it going?

We’ll tell you what to text a guy when conversation gets boring. Don’t worry – you’re not trapped in an uninteresting cycle forever, and it doesn’t mean your relationship is dead.

What to Text a Guy When Conversation Gets Boring

Ask him an interesting question to get him thinking.

Pleasing his mind is just as important as pleasing his body. By asking him unique questions, you’re showing him that you’re not the average conversationalist.

Depending on how he answers your questions, you’ll be able to ask him more in response to really get the conversation flowing.

We strongly recommend avoiding potentially controversial topics like politics, though. These types of subjects are better when you’ve known each other for awhile.


  • “Do you think there’s life on other planets?”
  • “Do you believe in ghosts?”
  • “What’s the craziest thing that’s ever happened to you?”
  • “If you could go back in time to witness anything, what would you want to see?”
  • “If you won the lottery, what’s the first thing you’d spend some of it on?”
  • “What’s your dream vacation?”

Related Article: What to Text a Guy After Being Ghosted (Do’s and Don’ts of Texting Post-Ghost)

Get involved in a new series with him.

"Nothing brings people together quite as well as a new TV show."

Nothing brings people together quite as well as a new TV show. Just think about all the memes, groups, clubs, and books that spin off of each popular series.

Getting into one together will give you tons of new things to talk about. If there’s a show that you know is on his watch list that he hasn’t gotten into yet, now’s the time.

Tell him you’ll watch it along with him. Even if you’re not physically watching it with him, you can watch it together from a distance and discuss each twist in the plot.


  • “I can’t believe what happened at the end of the season one!”
  • “What would you have done if you were *character from the show*?”
  • “Who’s your least favorite character?”
  • “Which character do you think you’d be best friends with?”

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Become book buddies.

Like TV shows, books are another binding force. Asking him about books will work especially well if he’s more the intellectual type.

Start reading a book that you know he loves. Ask him questions along the way or share your thoughts with him.

You’ll have plenty of new things to discuss, and can ask similar questions to what you’d ask about a show.


  • “Who is your favorite character and why?”
  • “If I were a character in the book, which one do you think I’d be? What about you?”

Talk music.

Everyone likes music. We may not all be aficionados, but we all have our favorite songs and most of us have made playlists before.

That’s why it’s the perfect thing to talk about if he’s a music buff. You can make playlists to for each other of songs that you think you’d like.

For extra fun, combine it with conversations about characters in books, shows, and movies. You can pick theme songs for each character and discuss why you picked each song.

Read Also: What to Text Him

Or you can get deep with him by asking him which songs mean the most to him and why. Make sure you listen to the music he suggests – this will show him that you’re paying attention and that you care about his interests.


  • “What’s one song you think I’d like that I probably haven’t heard yet?”
  • “If *book or show character* had a theme song, what do you think it would be?”
  • “What is your own personal theme song?”

Read Also: This is What to Text a Guy After Making Out

Get virtual and discuss games.

"You won't believe how much he'll light up when you ask him about the stories in his favorite games."

Recommended Article: What to Text a Guy after Sleeping with Him (How to Keep Him Interested)

It might sound nerdy, but trust us here.

Most people play games these days, whether those games are on a smartphone, computer, or gaming system. Chances are, he’s played games before, too.

If you’re worried about them taking up all his time, don’t be. Games are a great way for you to spend time with him by playing together or talking to him about them.

You won’t believe how much he’ll light up when you ask him about the stories in his favorite games.

You’ll also learn a lot about what makes him tick by knowing what games he likes. Video games come in a huge range of genres, including horror, sports, fantasy, sci-fi, and much more.

Based on which ones he plays the most, you’ll know which genres he likes. That opens up the door for suggesting dates in the future or other things he might enjoy to him.


  • “What are your top three favorite video games?”
  • “If you could visit the world in any video game, which one would you pick?”
  • “I bet I could beat you in a game of *multiplayer game title*.”
  • “Can you explain to me how *game title* works?”

Reminisce with him.

Have you known him for some time or been on a few dates already? Then talk over the high points of your dates or your conversations with him.

This will make him relive all those positive times you spent together. As a result, he’ll be reminded of how much he loves being with you.

Obviously, this approach only works if you’ve been talking to or seeing him for awhile. If you’re just starting to get to know him, you’ll probably need to skip this one (at least for now).


  • “Remember that time you took me surfing for the first time ever? It was so fun!”
  • “I still crack up when I remember that joke you told me the other day.”

Read Also: 15+ Things to Text a Guy After a First Date 

Spice up the conversation with a little naughtiness.

"When you so much as hint at sex, it's bound to make your guy sit up straighter and pay more attention as his heart starts racing."

Further Reading: What to Text a Guy to Catch His Attention (Without Seeming Clingy)

No matter what, sex is interesting. When you so much as hint at sex, it’s bound to make your guy sit up straighter and pay more attention as his heart starts racing.

If you’re looking for a serious relationship, though, avoid using this approach too much. He’ll start thinking all you want is sex, which could derail any potential romance.

This could be great for spicing up an old relationship, though, especially if you’re willing to get a little out of your comfort zone. For example, you could text him something sexy while you’re both at work to show him how badly you want him.


  • “What’s one thing you’ve always wanted to try in the bedroom?”
  • “Want to hear my craziest sexual fantasy?”
  • Send him a sexy selfie. (Bonus points if you achieve it while you’re at work – he’ll be turned on knowing you can’t stop thinking about him even while you’re working.)
  • “What’s your favorite part of my body…below my face?”
  • Tell him what your favorite part of his body is…and why.

Are you looking for more examples on what to say to get him hopelessly addicted to you? Our go-to source is the Text Chemistry program.

In it, Amy North, a romance expert, goes over psychological strategies you can use to make any guy long for you. It’s not difficult to use, and with her materials, you’ll have him daydreaming and lovesick for you all over again.

Lighten it up a bit.

Joking is wonderful for making everyone relax and open up. Just think about all the times your boss has opened a meeting with a lame joke, or the all the comedic relief characters in books, shows, and movies.

Telling him a joke or sending him a funny picture will make him smile. Even better, guys love a woman with a good sense of humor.

So making a well-timed joke will show him just that. He’ll love seeing how fun you can be.

You can get bonus points here by complimenting his sense of humor at the same time. Remind him of a good joke he made once to make him feel especially proud of himself.


  • Send him the worst pickup line you can find.
  • Tell him the first joke that comes to mind.
  • Ask him who his favorite comedian is (if he has one), and watch them for some quotes you can share.
  • Send him a meme that you think he’d like.

Challenge him to a little friendly competition.

This strategy is irresistible for a gamer guy. It encourages him to put more effort into the conversation now so he can “win.”

Here’s how it works: you’ll issue some kind of challenge to him. It can be in a game he plays, or it can be a bet you place on anything else.

Up the stakes by betting the next date on the outcome. Say whoever loses needs to pay for the next dinner or movie date.

Then sit back and watch him pour energy in the challenge as he tries to win against you.

No matter who wins or loses, though, you’ll be scoring another date out of it.


  • “I bet you dinner that you can’t beat my score in this game.” –Follow up with a screenshot of your score in an app or game you’re playing.
  • “One coffee date with yours truly says you can’t find a cheesier pickup line than me.”

Make plans with him.

While you’re talking, you might as well take the time to plan out the next date.

Make sure you plan it around his and your interests. Figuring out the details of the next date and deciding what to do next will give you plenty to discuss.

The bonus is that it will also get you excited to see each other again. This is especially true if you’re planning something really fun.


  • “Would you want to try the new bar with me sometime?”
  • “Are you interested in any new movies that are out?”
  • “I just bought this new game. How do you feel about coming over and trying it out with me?”

What to Avoid Texting Him When Conversation Gets Boring

Related Article: What to Text a Guy After He Cancels a Date (To Make Him Regret It)

Now that you have some ideas of what to talk about next, let’s discuss what you need to avoid in order to keep the conversation flowing.

Leave these things out of your text talk, and you’ll stand a much better chance of keeping the discussion alive and well.

One-word answers.

"In fact, nothing will kill a conversation faster, because using a one-word answer limits what he can respond with."

These don’t contribute anything to the conversation. In fact, nothing will kill a conversation faster, because using a one-word answer limits what he can respond with.

On top of that, one-word responses make you look boring and (maybe worst of all) uninterested. Use too many of them, and you can expect him to stop talking to you.

Strings of texts.

Texting a few times in a row is okay with your friends and family, but with a guy you’re just getting to know?

It’s a disaster. At best, he’ll think it’s a bit over the top and at worst, he’ll feel like you’re drowning him with attention.

On top of that, it makes you seem impatient for an answer, and like you don’t have anything to do other than talk to him.

Would you want to talk to someone if all they did was hove over their phone, waiting for you constantly? Probably not.

Controversial questions or statements.

We’ve said it before and we’ll say it again: avoid divisive subjects like politics or religion at first.

Of course, at some point, it can become important to know where he stands on these issues for long-term compatibility. But the beginning of a relationship is not the time to discuss them.

You can work your way up to these topics at a later time when you know each other better.

Excessively emotional messages.

This really depends on where you currently are in your relationship. But in general, you might want to resist the urge to write him a love letter by text, even if you think you’re falling for him.

It may be more acceptable later on, when you’ve discovered the feeling is mutual. However, in the earliest stages of a relationship or if you’re hoping for something more casual, you’ll want to stay away from emotional gushing.

You risk driving him away from you, otherwise.

Still Running Out of Things to Say?

We know what it’s like to feel a conversation dying down with someone we like. It can be extremely disheartening, to say the least.

But it doesn’t mean your relationship is done for. If you need help reviving the conversation between you, there are always extra resources you can use to turn any talk around.

Our personal favorite is the Text Chemistry Course by dating aficionado Amy North. She has tons of texts and tips to choose from to help you invigorat

Jenny Muscolo
Jenny Muscolo

My name is Jenny and I love helping people with their relationships. I got my Masters in human sexuality at Northwestern University, and love what I do.

I believe a few simple tips can help you massively improve your communication skills with your partners, which leads to better interactions. Thanks for visiting!