20 Flirty Texts To Keep Him Thinking About You

The right text message can make someone’s entire day brighter and keep you on their mind long after they’ve read it.

Flirty texting is an art that combines playfulness, genuine interest, and just the right amount of mystery.

These carefully crafted messages will help you create meaningful connections while showing your personality and keeping the conversation exciting and engaging.

Sweet and Romantic Messages

1. “I was just thinking about that smile of yours and couldn’t help but smile myself. Hope you’re having an amazing day!”

This message works because it’s genuine and specific. You’re not just saying you’re thinking about him – you’re sharing exactly what you’re thinking about and how it makes you feel.

The mention of his smile creates a positive association and makes him more likely to smile when he reads your text.

It’s a sweet cycle that connects your happiness to his presence in your life.

The well-wishes for his day show that you care about his wellbeing beyond just your romantic interest.

This balance of flirtation and genuine care creates deeper connection than purely flirty messages.

2. “You have this amazing way of making ordinary moments feel special. Can’t wait to create more memories with you.”

This text acknowledges something specific about his personality while expressing excitement about your future together.

It shows you’re paying attention to how he makes you feel.

The forward-looking element creates anticipation for your next meeting while remaining positive and pressure-free.

You’re expressing interest without being demanding about specific plans.

By focusing on “ordinary moments,” you’re showing that you value his company even during simple, everyday activities. This makes him feel appreciated for who he is naturally.

3. “Just heard our song on the radio and got the biggest smile thinking about you. Music will never sound the same!”

Referencing shared experiences creates intimate connections that feel special and unique to your relationship.

“Our song” implies a deeper bond than casual dating.

The image of you smiling while thinking about him gives him a clear picture of how you feel.

Men often appreciate direct communication about emotions, and this achieves that sweetly.

The playful exaggeration about music never sounding the same adds humor while emphasizing how much he’s impacted your life. It’s romantic without being overly dramatic.

Playful and Teasing Messages

4. “Warning: You’ve been on my mind all day. Side effects may include random smiling and daydreaming. No known cure.”

The medical warning format adds humor while delivering a sweet message about how much you’re thinking about him.

The playful structure makes the sentiment less intimidating.

Mentioning “random smiling” gives him a clear picture of how thinking about him affects you throughout the day.

This visual element makes the message more engaging and memorable.

The “no known cure” line suggests that thinking about him is something you enjoy and don’t want to stop.

It’s a clever way to say you’re happily smitten without being too serious.

5. “I have a confession: I may have been a little distracted at work today thinking about last night. Worth every missed email!”

This message creates intrigue by referencing a recent shared experience while maintaining some mystery about what specifically has you distracted.

The confession format adds playfulness while the mention of being distracted at work shows that thoughts of him are affecting your daily life in a positive way.

The humor about missed emails keeps the tone light while emphasizing that thinking about him feels more important than work tasks. It’s a sweet way to show your priorities.

6. “Question: Is it normal to check your phone this often hoping for a text from someone amazing? Asking for a friend… 😉”

The “asking for a friend” setup is a classic playful way to share feelings while maintaining some emotional distance through humor.

This message lets him know you’re hoping to hear from him without seeming needy or demanding. The playful format makes it safe for both of you to express interest.

The winking emoji adds flirtation while making it clear you’re being playfully obvious about the “friend” being yourself. It invites him to play along with the humor.

Complimentary and Confidence-Boosting Messages

7. “Your laugh is seriously one of my favorite sounds in the world. Hope I can hear it again soon!”

Specific compliments about personality traits feel more genuine than generic appearance-based comments.

Focusing on his laugh shows you pay attention to details that make him unique.

This message also implies that you enjoy making him laugh, which suggests compatibility and shared humor. It positions you as someone who brings joy to his life.

The hope to “hear it again soon” subtly suggests wanting to spend time together without being pushy about making specific plans immediately.

8. “You looked absolutely incredible today. Still thinking about how handsome you are and smiling like an idiot.”

Direct compliments about appearance can boost confidence, especially when delivered with genuine enthusiasm.

The specific timing (“today”) shows you’re paying attention to him regularly.

The self-deprecating humor about “smiling like an idiot” makes the compliment feel more authentic and less intimidating.

It shows you’re comfortable being vulnerable about your feelings.

This message works best when sent after you’ve seen him in person, creating a connection between your real-world interactions and your text conversations.

9. “I love how passionate you get when you talk about things you care about. Your enthusiasm is incredibly attractive.”

This compliment goes deeper than surface-level traits to acknowledge something meaningful about his personality and character.

Calling his passion “attractive” creates a romantic connection to admirable personality traits. It shows you’re drawn to who he is as a person, not just how he looks.

This type of message often leads to deeper conversations about interests and values, helping build more meaningful connections beyond casual flirtation.

Building Anticipation Messages

10. “I have something fun planned for our next date, but you’ll have to wait to find out what it is. Hope you like surprises!”

Creating anticipation for future meetings keeps you on his mind and gives him something to look forward to.

The mystery element adds excitement to your upcoming plans.

This message shows initiative in planning while maintaining an element of surprise that keeps things interesting.

It demonstrates that you’re thinking ahead about your time together.

The playful withholding of information creates a fun dynamic where he might try to guess or ask for hints, leading to more engaging conversation.

11. “Fair warning: I’m plotting ways to make you smile the next time I see you. Consider yourself warned!”

The “warning” format adds humor while communicating your intention to bring joy to his life. It shows you think about his happiness and plan accordingly.

This message creates positive anticipation about your next meeting while positioning you as someone who actively tries to make him happy.

The playful “plotting” language adds intrigue while making it clear your intentions are entirely positive and caring.

12. “Can’t decide what I’m looking forward to more about seeing you this weekend – your stories, your laugh, or just being near you.”

This message lists specific things you enjoy about his company, showing that you value multiple aspects of spending time together.

The uncertainty about what you’re most excited about suggests that everything about him appeals to you, which is incredibly flattering and confidence-boosting.

Mentioning “just being near you” adds a romantic element while keeping the message sweet rather than overly intense.

Showing Interest and Care Messages

13. “How did your presentation go today? I’ve been thinking about you and hoping it went amazingly well!”

Remembering important events in his life shows genuine care and attention.

This type of message demonstrates that you listen when he talks and care about his success.

The timing of checking in after an important event shows thoughtfulness and creates opportunities for him to share his experiences with you.

This message opens the door for meaningful conversation about his work or interests, helping build deeper connection beyond just romantic attraction.

14. “Saw this and thought of you immediately. Hope it makes you smile as much as thinking of you makes me smile!”

This message works well when paired with a funny meme, interesting article, or photo that relates to his interests or something you’ve discussed together.

The connection between making him smile and how thinking of him makes you smile creates a sweet reciprocal dynamic that emphasizes mutual happiness.

Sharing things that remind you of him shows he’s on your mind during daily activities and that you want to include him in moments of joy or interest.

15. “I know you’ve got a lot going on this week, but don’t forget to take care of yourself. You matter to me!”

This message shows awareness of his stress levels and demonstrates caring about his wellbeing beyond just your romantic relationship.

The reminder to take care of himself positions you as someone who supports his health and happiness, which builds trust and deeper connection.

Ending with “you matter to me” is a clear but not overwhelming way to express growing feelings while showing genuine care for his wellbeing.

Mysterious and Intriguing Messages

16. “I have a secret about you, but I’m saving it for when I see you next. Get ready for some good news!”

Creating mystery about positive information builds anticipation while ensuring he knows whatever you’re withholding is something good.

This message guarantees future conversation and gives him something to wonder about until you next meet in person.

The promise of “good news” creates positive anticipation rather than anxiety, making this a feel-good mystery that enhances your connection.

17. “You’ll never guess what happened today that made me think of you. Story time when we talk later!”

This message creates anticipation for your next conversation while implying that things in your daily life remind you of him regularly.

The promise of “story time” suggests that you have interesting things to share and that your conversations are engaging and enjoyable.

This type of message often leads to longer, more meaningful conversations where you share experiences and build deeper connections.

18. “I may have done something that would make you proud of me today. Hint: it involves that advice you gave me last week!”

Referencing previous conversations shows you value his input and actually listen to his advice, which most people find very flattering.

The mystery about what you did creates anticipation while the mention of him being “proud” positions him as someone whose opinion matters to you.

This message shows personal growth and gives credit to his positive influence in your life, which strengthens your bond and builds his investment in your success.

Confident and Bold Messages

19. “I hope you’re prepared for how much I’m going to spoil you this weekend. Fair warning: I might be a little extra!”

This message shows confidence in your feelings and intentions while creating anticipation for your upcoming time together.

The “fair warning” format adds humor while the mention of being “extra” suggests enthusiasm and playfulness in how you express affection.

Talking about spoiling him shows generosity and care while positioning yourself as someone who actively works to make him happy.

20. “Just so you know, you’re the best part of my days lately. Thanks for being amazing without even trying!”

This direct expression of appreciation shows emotional maturity and confidence in sharing your feelings honestly.

The phrase “without even trying” suggests that his positive impact on your life comes naturally, which is incredibly flattering and shows authentic attraction.

This message balances vulnerability with confidence, showing you’re comfortable expressing genuine feelings while appreciating him for who he naturally is.

Tips for Successful Flirty Texting

Timing matters significantly when sending flirty texts.

Avoid sending messages during known busy periods or very late at night unless you’ve established that communication pattern.

Pay attention to his response patterns and energy levels.

If he typically sends short responses, match that energy rather than overwhelming him with lengthy messages.

Balance is crucial in flirty texting. Mix sweet messages with playful ones, and avoid sending multiple texts in a row without responses.

Personalization makes every message more effective.

Reference shared experiences, inside jokes, or specific things you know about his interests and personality.

Conclusion

These flirty texts help create genuine connections through playful, caring communication that shows interest while maintaining the excitement and mystery of new romance.