Last Tuesday, I sent my boyfriend a random text at 2 PM. Nothing wild, just a sweet little note. He called me during his break, grinning like an idiot, saying it made his entire afternoon. I realized something: a well-timed message is like sneaking chocolate into his boring Tuesday meeting.
Work texts are an art. You want to brighten his day without distracting him from that big presentation. You want to be the notification he’s actually excited to see. These 56 messages are designed to make him smile, laugh, or even blush a little, all while he’s stuck at his desk pretending to care about spreadsheets.
I’ve split these into categories so you can match your mood to his vibe. Sweet ones for when you’re feeling soft. Funny ones for when you know he needs a laugh. And yes, some flirty ones for when you want to remind him what’s waiting at home.
Think of this as your texting playbook. Whether you’ve been together two months or two years, these messages work because they’re genuine, not generic. Let’s make his workday a little less boring.
Sweet and Supportive Messages
Work can be draining. Sometimes he just needs to know you’re in his corner, cheering him on from wherever you are. These messages are the virtual equivalent of a warm hug. They’re perfect for those days when he mentioned a tough meeting or when you just want to be his biggest fan.
Use these when he’s stressed or when you want to remind him he’s loved without any pressure. Sweet doesn’t mean boring. It means thoughtful. And honestly, guys love feeling supported just as much as we do.
1. “Just wanted to say I’m really proud of you. You’re crushing it today.”
This works because it acknowledges his effort without needing details.
2. “Thinking about you and hoping your day is going as amazing as you are.”
Simple, direct, and impossible not to smile at.
3. “You’ve got this. And when you’re done, you’ve got me too. ❤️”
The combo of confidence boost and promise makes this one powerful.
4. “Can’t wait to hear about your day later. I know you’re handling everything like a boss.”
Shows genuine interest in his life beyond just romance.
5. “Sending you all the good vibes for that meeting. You’re going to nail it.”
Perfect for when he’s mentioned something specific he’s nervous about.
6. “I believe in you more than you probably believe in yourself right now.”
A reality check wrapped in love.
7. “Just a reminder that you’re doing an incredible job at life.”
Broadens the compliment beyond just work.
8. “Hope your coffee is strong and your day is short. You deserve an easy one.”
Relatable and shows you get the workday struggle.
9. “Whatever happens today, you’re still my favorite person.”
Takes pressure off and reassures him.
10. “I’m your biggest fan, even when you’re just answering emails.”
Makes the mundane feel special.
11. “You make hard work look easy. That’s pretty sexy, honestly.”
Mixes support with a little flirtation.
12. “Halfway through the day! You’re almost free to do whatever you want. Hopefully that includes me.”
Encouraging with a playful twist at the end.
Funny and Playful Messages
Laughter is the fastest way to someone’s heart, especially when they’re stuck in a boring meeting. These messages are designed to make him chuckle, shake his head, or text back immediately with a laughing emoji. Use these when you know he needs a mental break or when you’re feeling cheeky.
Humor shows your personality. It also shows you don’t take everything too seriously, which is honestly refreshing in a relationship. Plus, being the person who makes him laugh at work? That’s relationship gold.
13. “Just saw a dog wearing a tie and thought of you. You’re both very professional.”
Absurd comparison that’s impossible not to laugh at.
14. “On a scale of 1 to 10, how badly do you want to fake a fire drill right now?”
Acknowledges the work struggle with humor.
15. “I’m bored. You’re probably bored. Let’s be bored together later.”
Relatable and makes plans in the cutest way.
16. “Do you think your coworkers know you’re texting the coolest person ever right now?”
Playful confidence that’s hard to resist.
17. “Just ate lunch and thought of you. Mostly because I didn’t share.”
Teasing in the best way possible.
18. “If I was there, I’d steal your lunch. Just so you know.”
Shows comfort and playfulness in your dynamic.
19. “Work is temporary. My love for you is permanent. Also, what’s for dinner?”
Sweet with a practical twist.
20. “I bet you look cute even when you’re pretending to pay attention in meetings.”
Flirty observation that’s also funny.
21. “Remember when you said work wasn’t that bad? You lied.”
Calls him out playfully.
22. “Sending you telepathic messages to leave early. Is it working?”
Silly and sweet.
23. “Just wanted to interrupt whatever boring thing you’re doing to say hi.”
Honest and direct humor.
24. “You’re probably doing something important right now. I’m eating chips. We’re both winning.”
Self-deprecating and funny.
25. “If I sent you 100 texts today, would that be supportive or annoying?”
Meta humor that acknowledges texting habits.
26. “Your job is lucky to have you. But not as lucky as I am.”
Sweet ending to a playful sentiment.
Flirty and Teasing Messages
Now we’re getting into the fun zone. These messages add a little spice to his day without crossing into inappropriate territory for work. They’re perfect for reminding him you’re thinking about him in more than just a friendly way. Use these when you’re feeling confident or when you want to build anticipation for later.
Flirty texts work because they create tension. The good kind. The kind that makes him think about you instead of that boring spreadsheet. Just make sure you know his work situation before sending anything too bold.
27. “Can’t stop thinking about how good you looked this morning.”
Visual reminder that flatters him.
28. “What are you wearing? And can I help you take it off later?”
Playful with clear intention.
29. “Just a heads up: I’m planning something fun for tonight.”
Creates anticipation and mystery.
30. “You’re really distracting me today. Even when you’re not here.”
Shows he’s on your mind in a flirty way.
31. “I have a confession: I’ve been thinking about kissing you all day.”
Direct but still sweet enough for work hours.
32. “Do you think about me as much as I think about you? Because it’s getting ridiculous.”
Vulnerable and flirty combo.
33. “I’m counting down the hours until I see you again.”
Shows excitement without being too forward.
34. “You better hurry home. I miss your face. And other things.”
Cheeky ending that hints at more.
35. “Just wanted to remind you that you’re incredibly attractive.”
Straightforward compliment that works every time.
36. “Tonight’s going to be fun. I’m already thinking of ideas.”
Builds excitement for quality time together.
37. “I might have a surprise for you later. No hints.”
Mystery keeps him guessing and interested.
38. “You’re the best part of my day, even when you’re not actually with me.”
Romantic with a flirty undertone.
39. “Fair warning: I’m feeling extra affectionate today.”
Sets expectations in a playful way.
40. “Can we skip to the part where you’re home and we’re cuddling? Or whatever.”
The “or whatever” adds cheeky ambiguity.
Just Because Messages
Sometimes the best texts are the ones with no agenda. No occasion. No reason except you thought of him. These messages are casual, low-pressure, and perfect for any day. They show you care without needing a big moment.
Use these when you want to stay connected but don’t want to overthink it. They’re the texting equivalent of a smile across the room.
41. “Hey you. Just wanted to say hi.”
Simple and sweet.
42. “Saw something that reminded me of you. Made me smile.”
Shows he’s on your mind organically.
43. “How’s your day going? For real.”
Genuine check-in that invites conversation.
44. “Random thought: You’re pretty great.”
Casual compliment that feels natural.
45. “Hope work isn’t too terrible today.”
Empathetic without being dramatic.
46. “Thinking about you. That’s all.”
Direct and straightforward.
47. “You make my days better. Even the boring ones.”
Acknowledges his impact on your life.
48. “Can’t wait to see you later. Even if we just sit around.”
Values time together over activity.
49. “You popped into my head. Now you’re stuck there.”
Playful way to say you’re thinking of him.
50. “Just wanted to send some love your way. ❤️”
No explanation needed, just affection.
Encouragement for Tough Days
We all have those days. The ones where everything goes wrong and you just want to hide under your desk. These messages are for when he’s mentioned stress or when you can tell from his vibe that work is kicking his butt. They’re supportive without being patronizing.
Send these when he needs to know someone’s rooting for him, even from afar.
51. “Rough day? Remember, you’ve survived 100% of your bad days so far.”
Perspective with encouragement.
52. “You’re stronger than whatever’s thrown at you today.”
Confidence boost wrapped in truth.
53. “Bad days don’t last forever. But I’m here regardless.”
Reassuring presence.
54. “Take a deep breath. You’ve got this. And if you don’t, we’ll figure it out together.”
Partnership acknowledgment.
55. “Some days are just hard. Doesn’t mean you’re failing.”
Permission to struggle without shame.
56. “Almost done. Then it’s just you, me, and whatever makes you happy tonight.”
Light at the end of the tunnel.
When to Send Work Messages
Timing matters. You don’t want to be the reason he gets side-eye from his boss. Here’s how to nail it:
Mid-morning is golden. Around 10 or 11 AM, he’s likely settled into work but not drowning yet. A sweet message lands perfectly here.
Lunch breaks are safe zones. He’s definitely checking his phone. This is prime time for flirty or funny texts.
Avoid crucial meetings. If you know he has a big presentation or client call, wait until after. You want to brighten his day, not distract him during a make-or-break moment.
Late afternoon works too. Around 3 or 4 PM when energy dips, your text can be the boost he needs to finish strong.
Know his schedule. Everyone’s workday is different. Pay attention to when he usually texts back. That’s your window.
One or two texts max. Unless he’s responding and engaging, keep it to one thoughtful message. You’re enhancing his day, not demanding attention.
The goal is to be a bright spot, not a buzzkill.
What If He Doesn’t Respond Right Away
Don’t panic. Seriously. He’s at work. His phone might be in a drawer. He might be in back to back meetings. A delayed response doesn’t mean he doesn’t care.
Give him space. Resist the urge to send a follow up immediately. Let your message sit. He’ll see it when he has a moment.
Consider his job. Some jobs make phone checking impossible. If he’s in healthcare, construction, teaching, or any hands-on role, delays are normal.
Look for patterns. If he never responds during work hours but always texts after, that’s just his style. Work with it, not against it.
Don’t make it a thing. When he does respond, don’t say “Finally!” or “Took you long enough.” That kills the vibe.
Save deep conversations for later. Work texts should be light. If you need to talk about something serious, wait until he’s home.
Trust matters here. If you trust him, you trust he’ll respond when he can.
How to Customize These for Your Relationship
Match your energy to his. If he’s more reserved, skip the super flirty ones and stick with sweet or funny. If he loves banter, go heavy on playful teasing.
Use inside jokes. Replace generic phrases with things only you two would get. That personal touch makes any message better.
Consider relationship length. New relationship? Keep it lighter. Been together forever? You probably know exactly what he needs to hear.
Pay attention to his responses. If he loves when you’re funny, send more of those. If he lights up at sweet messages, lean into that.
Be yourself. Don’t force a tone that doesn’t fit you. Authenticity always wins over trying too hard.
Think about his personality. Is he sentimental? Send supportive messages. Is he sarcastic? Hit him with humor.
The best messages are the ones that sound like you, not like you’re reading from a script.
There you have it. 56 messages that’ll make his workday infinitely better. Whether you’re going sweet, funny, flirty, or all of the above, the point is simple: show him you’re thinking about him.
Don’t overthink it. Pick one that feels right and hit send. The magic isn’t in the perfect words. It’s in the fact that you took a minute out of your day to brighten his.
And honestly? The best part is watching him light up when he reads it. That’s worth way more than any fancy text could ever be.
Now go make his phone the best notification he gets all day. And if you’re looking for more ways to keep the spark alive, check out our articles on date night ideas and conversation starters. Happy texting!