What To Text A Guy When Conversation Gets Boring

Occasionally, despite being with an exceptional individual, the exchange of dialogue may begin to dwindle.

This does not necessarily indicate any wrongdoing on your or his part; it is simply natural to exhaust topics of discussion.

Sending basic "how are you" texts can be a good way to initiate a conversation, but how can one sustain it?

We'll provide you with some text ideas for when the conversation with a guy becomes dull. You needn't fret, as this doesn't imply that you're stuck in an unstimulating rut indefinitely, nor does it signify the demise of your relationship.


Ask him an interesting question to get him thinking

Satisfying his intellect is equally significant as satisfying his physical desires. By asking him uncommon questions, you're demonstrating that you're not an ordinary converser.

Based on his answers to your inquiries, you can ask more follow-up questions to truly stimulate the conversation.

We highly advise refraining from discussing potentially contentious topics such as politics. It's best to reserve these kinds of subjects for when you've built a more established relationship.


"Do you believe in the existence of extraterrestrial life?"

"Do you have any belief in ghosts?"

"What's the most unusual experience you've ever had?"

"If you had the opportunity to travel back in time and witness any event, what would you choose to see?"

"What would be the first thing you'd spend some of your lottery winnings on?"

"What would be your ideal vacation destination?"

Get involved in a new series with him

Few things bring individuals together as effectively as a new television series. Consider all the memes, groups, clubs, and books that emerge from each widely embraced show.

Watching a show together can provide you with a plethora of new conversational topics. If there's a program that you're aware is on his viewing list, but he hasn't watched it yet, now is an excellent opportunity.

Let him know that you'll join him in watching it. Even if you're not physically together, you can still watch it simultaneously and analyze each plot twist together.


"I'm stunned by what occurred at the conclusion of season one!"

"What choices do you think you would have made if you were character from the show?"

"Which character do you dislike the most?"

"Which character do you believe you would be closest friends with?"

Become book buddies

Similar to TV shows, books are another avenue for fostering a shared bond. Inquiring about his reading habits will be particularly effective if he's more of an intellectual individual.

Begin reading a book that you know he adores. Along the way, ask him questions or share your opinions with him.

You'll have a wealth of fresh material to discuss, and you can pose similar inquiries to what you would ask regarding a TV show.


"Which character is your favorite, and what makes them stand out to you?"

"If I were a character in the book, who do you think I would resemble? And which character would you see yourself as?"

Talk music

Music is universally appealing. While we may not all be experts, we all have our preferred tunes, and many of us have crafted playlists.

This is why it's an excellent topic to broach if he's a music aficionado. You can exchange playlists containing songs that you believe the other person will enjoy.

To enhance the enjoyment, incorporate it with discussions about characters in books, shows, and movies. You can select theme songs for each character and deliberate on why you chose each tune.

Alternatively, you can delve deeper by asking him which songs hold the most significance to him and why. It's important to listen to the music he recommends, as it demonstrates that you're attentive and value his interests.


"What's a song that you think I'd enjoy, but I may not have heard it before?"

"If book or show character had a theme song, what song do you think would fit them the most?"

"If you had to choose one song as your personal theme song, what would it be and why?"

Get virtual and discuss games

It might sound nerdy, but that is true.

Most people these days play games, whether it's on a smartphone, computer, or gaming system. It's likely that he has played games before, too.

Don't worry about games taking up all his time, as they can actually be a great way for you to spend time with him. You can either play games together or talk to him about the games he enjoys.

You'll be surprised how much he'll light up when you ask him about the stories in his favorite games.

Knowing what games someone likes can reveal a lot about what makes them tick. With video games covering a wide range of genres, including horror, sports, fantasy, sci-fi, and more, there's plenty to learn.

By identifying the games he plays the most, you can determine which genres he prefers, giving you the opportunity to suggest future dates or other activities that he may enjoy.


"What are your three most favorite video games?"

"If you could choose any video game world to visit, which one would you choose?"

"I'm confident that I could win against you in multiplayer game title."

"Could you provide me with an explanation of how game title functions?"

Reminisce with him

If you have known him for some time or been on a few dates already, discuss the highlights of your dates or your previous conversations with him.

This will allow him to reminisce about all the positive moments you shared together, which may remind him of how much he enjoys being with you.

Of course, this strategy is only effective if you have been in regular communication or have spent time with him before. If you are still getting to know him, you may need to skip this approach, at least for the time being.


"Do you recall when you took me surfing for the first time? It was such a great experience!"

"I still find it funny when I recall the joke you shared with me the other day."

Spice up the conversation with a little naughtiness

Regardless of the context, sex is always an intriguing topic. Even the slightest insinuation of sex is likely to grab your guy's attention and cause his heart rate to increase.

However, if you are seeking a genuine and committed relationship, it is advisable to avoid using this strategy excessively. Continuously bringing up sex may give him the impression that you are only interested in a physical relationship, which could jeopardize any possibility of a genuine romance.

If you're looking to add some excitement to a long-term relationship, this strategy could be effective, particularly if you're willing to step out of your comfort zone. For instance, you could send him a sexy text message while you're both at work to express how much you desire him.


"What is something you have always been curious to try in the bedroom?"

"Would you be interested in hearing about my wildest sexual fantasy?"

Sending a seductive selfie could be an option (extra credit if you manage to do so while you're at work; it can make him feel desired knowing you're thinking about him even during working hours).

"What is your favorite part of my body, excluding my face?"

Let him know what your favorite part of his body is, and explain why you are fond of it.

If you are seeking additional examples of what to say to make him captivated by you, we recommend the Text Chemistry program as our primary source.

The Text Chemistry program, created by relationship expert Amy North, provides insights into psychological techniques that can be utilized to make any man desire you. With its user-friendly interface and helpful resources, you can easily employ her methods to make him long for you and be smitten with you once more.

Lighten it up a bit

Humor is an effective tool for easing tension and promoting openness. Consider the number of times your boss has commenced a meeting with a corny joke or the numerous comedic characters featured in books, shows, and films.

Sharing a joke or sending a humorous picture to him is an effective way to brighten his day and elicit a smile. Moreover, men typically appreciate a woman who possesses a great sense of humor.

Therefore, delivering a well-timed joke will demonstrate to him that you possess a lighthearted and fun-loving nature. This will undoubtedly appeal to him and make him appreciate your sense of humor even more.

You can earn bonus points by simultaneously praising his sense of humor. Recall a time when he made a particularly good joke and remind him of it to make him feel especially proud of himself. This will undoubtedly bolster his confidence and increase his fondness for you.


Send him the cheesiest or most cringe-worthy pickup line you can come up with or find.

Tell him the first joke that comes to your mind, even if it's silly or doesn't make much sense. It's a lighthearted way to start a conversation and make him laugh.

Ask him if he has a favorite comedian and if so, who it is. Then, look up some of their jokes or quotes and share them with him. It's a great way to connect over a shared sense of humor and shows that you're interested in his interests.

You can share a meme that relates to a shared interest or a joke that you know he'll find funny. It's a simple yet effective way to make him laugh and feel like you're on the same wavelength. Just be sure to choose a meme that's appropriate and won't offend him in any way.

Challenge him to a little friendly competition

If you're chatting with a gamer guy, try using this strategy. It can motivate him to engage more in the conversation and put in more effort to "win."

The basic idea of this strategy is to issue a challenge to your guy that encourages him to put more effort into the conversation in order to "win". The challenge can be related to a game he plays or a bet placed on something else.

Increase the level of excitement by suggesting a higher stake, such as betting on who will plan the next adventure or who gets to choose the activity for the next date. Whoever loses has to go along with the winner's plan.

Sit back and enjoy watching him pour his energy into the challenge as he tries his best to win against you.

Regardless of who comes out as the winner, the end result will be another date for both of you.


"How about a friendly wager? I'm willing to bet a dinner that you won't be able to beat my score in this game. Are you up for the challenge?"

"You won't find a cheesier pickup line than mine, guaranteed, just by agreeing to a coffee date with me."

Make plans with him

While conversing, it's a good opportunity to also consider planning for the next date.

Ensure that the next date caters to both your and his interests. Coordinating the specifics of the outing and determining the next steps can provide ample topics for conversation.

An additional benefit is that it will also generate anticipation for your next meeting, particularly if you're organizing an enjoyable activity.


"Would you be interested in trying out the new bar with me at some point?"

"Have you been keeping up with any new movies that have been released? Are there any that pique your interest?"

"I recently purchased this new game. Would you be interested in coming over to try it out with me?"


Now that you have a few conversation starters, let's talk about what topics to steer clear of to maintain a smooth and uninterrupted dialogue.

By omitting these topics from your text conversations, you significantly increase the likelihood of sustaining an engaging and lively discussion.

One-word answers

These don't add any value to the conversation. On the contrary, nothing shuts down a conversation more quickly than a one-word response, as it restricts the range of possible follow-up replies.

Moreover, one-word responses can make you appear uninteresting and disinterested, which could be even worse. If you rely on them excessively, don't be surprised if he loses interest in conversing with you.

Strings of texts

It may be acceptable to exchange multiple texts in a row with your friends and family, but is it appropriate when communicating with a guy you're still getting to know?

It could be a disaster. At best, he may consider it excessive, and at worst, he could feel suffocated by the overwhelming amount of attention.

Additionally, it could give the impression that you're eager for an immediate response and have nothing else to occupy your time other than conversing with him.

Would you want to converse with someone who just hovers over their phone, constantly waiting for your reply? Most likely not.

Controversial questions or statements

As we've mentioned before, it's best to steer clear of divisive topics like politics or religion, particularly in the early stages of getting to know someone.

Naturally, at some point, it could be crucial to understand his stance on these matters for long-term compatibility. Nevertheless, the start of a relationship is not the opportune moment to delve into these topics.

You can gradually introduce these subjects at a later time when you have a better understanding of each other.

Excessively emotional messages

This primarily depends on the current status of your relationship. However, as a general guideline, you may want to refrain from expressing your feelings in a lengthy text, even if you believe you're developing strong emotions for him.

It may be more appropriate to express your emotions later on, once you have established that the feeling is mutual. However, in the initial phases of a relationship or if you're seeking a more casual dynamic, it's best to avoid excessive emotional expression.

Otherwise, you risk pushing him away.