How to Flirt with Him Over Text (Without Feeling Cringey)

Published:

Updated:

Author:

flirty texts for him,

Disclaimer

As an affiliate, we may earn a commission from qualifying purchases. We get commissions for purchases made through links on this website from Amazon and other third parties.

We are a professional review company that receives compensation from companies whose products we review. We test each product thoroughly and give high marks only to the ones that are the very best. We are independently owned, and the opinions expressed here are our own.

Y’all, we’ve all been there. You’re staring at your phone, trying to come up with that perfect flirty text that’s cute but not too much, right? You want him to grin when he reads it, not think, “Bless her heart,” or worse, leave you hanging. Trust me, as a single mom from the South, I know all about busy days and tryin’ to figure out this whole dating thing again. But don’t worry, flirting over text doesn’t have to feel like such a chore.

By the end of this, you’ll know just how to keep the conversation fun and light without breaking a sweat—or overthinking it to death.

Why Flirting Over Text Can Be a Game-Changer

texting a guy, rules for texting guys, texting a guy first

Flirting over text is like a sweet little wink—you’re showing interest without going overboard. Whether you’re just gettin’ to know each other or y’all’ve been on a few dates already, a cute text can make his day (and yours, too). Plus, it’s perfect for those days when you’re runnin’ around like a chicken with your head cut off—like between work, soccer practice, and everything else that comes with mom life. A flirty text here and there is a fun way to keep him thinkin’ about you, even when you’re knee-deep in laundry.

Want even more ideas for flirtin’ over text? Check out this next article with tips that’ll have him smilin’ at his phone in no time!

How to Craft the Perfect Flirty Text (Without Givin’ Yourself a Headache)

text to a girl, text that girl, the best message to send a girl

1. Keep It Light & Playful

Flirtin’ should be fun, not stressful. Think of it like winkin’ at him from across the room—just enough to get his attention without makin’ it a big deal. You don’t have to come up with somethin’ deep or poetic every time. Sometimes, it’s the light, playful texts that do the trick:

  • “I bet you smile every time my name pops up on your screen 😉.”
  • “I was gonna wait for you to text me first, but patience has never been my strong suit 😏.”

Keep it sweet and simple, with a little hint of sass. Don’t go overboard with the emojis—one or two will do. We don’t wanna look like we’re back in middle school, right?

Curious about which emojis to use for a little extra flirtin’? Head on over to this article to find the perfect ones that’ll keep him guessin’ and grinnin’!

2. Use Humor (Because Who Doesn’t Love to Laugh?)

If there’s one thing I know about Southern charm, it’s that humor can get you just about anywhere. Guys love it when you can make ’em laugh, so don’t be afraid to add a little humor into your flirty texts:

  • “I think you owe me a drink. I’ve been thinkin’ about you way too much, and now I’m distracted… obviously, we need to meet up 😉.”

This keeps things lighthearted and shows him you’re not takin’ it all too seriously. Plus, it gives him a reason to smile when he reads your message.

3. Compliment Him, But Make It Unique

Everyone loves a good compliment, but darlin’, we’re not here to give the same ol’ “you’re cute” line. Go deeper than that and compliment somethin’ unique about him:

  • “You’ve got that kind of confidence that doesn’t need to be loud, and it’s definitely workin’ for you.”
  • “I can’t put my finger on it, but you’ve got this charm about you that’s just so easy to be around.”

It’s more personal, and it shows him you’re not just focusin’ on looks, which guys appreciate way more than you’d think.

Feelin’ ready to send that perfect flirty text, but want a little more inspiration? Watch the video below for even more fun ideas and real-life examples. Whether you’re just gettin’ started or want to turn up the charm, this video’s got all the tips you need!

tc video3

Flirty Text Ideas for Every Stage of Dating

winking eye box smiley mJ8MZf L

Just Gettin’ to Know Him

If y’all are in the early stages, where every text feels like it’s a big deal, try somethin’ playful that doesn’t come on too strong:

  • “I can’t decide if you’re more trouble or more fun, but I guess I’ll find out 😉.”

It’s flirty, but it still leaves a little mystery. And who doesn’t love a good mystery?

Already Been on a Few Dates?

Once y’all have hung out a few times and you’re more comfortable with each other, it’s time to up your game a little. Here’s somethin’ sweet and a little more direct:

  • “I swear I was gonna focus today, but then I thought about you… now nothin’s gettin’ done 😅.”

It’s a great way to remind him that he’s on your mind, without goin’ over the top.

Addin’ a Little Tension

Sometimes, flirtin’ is all about creatin’ a little playful tension. If you’re feelin’ bold, try somethin’ like this:

  • “So, what are you doin’ this weekend… besides thinkin’ about me, of course 😉.”

It’s just enough to make him smile and wonder what you’re up to.

Flirtin’ Fails: What Not to Do

stop sign isolated on white GklpLLsO

We’ve all had those moments where we send a text and immediately think, “Why did I say that?” Here are a few common mistakes to avoid:

1. Overthinkin’ It

The more you stress over what to say, the more likely it’s gonna come out awkward. Just be yourself and let it flow. It’s a text, not a marriage proposal, y’all.

2. Textin’ Too Much

Nobody likes feelin’ smothered, and blowin’ up his phone all day might give him that impression. Play it cool and let the conversation flow naturally.

3. Being Too Vague

Don’t be so subtle that he doesn’t even realize you’re flirtin’. A plain ol’ “Hey” without any fun or flirty follow-up isn’t gonna get you anywhere.

Flirty Texts Aren’t Just for New Relationships

man texting and smiling

Here’s the thing—flirtin’ doesn’t have to stop once you’re in a relationship. Even after y’all have been together for a while, keepin’ that playful, flirty vibe alive can make a world of difference. I’ve been married before, so I know how easy it is to fall into a routine. But a sweet text now and then can remind him that the spark’s still there:

  • “Remember when we first met and I couldn’t stop smilin’ around you? Still happens every time I see you ❤️.”

It’s simple, but it keeps things fresh, no matter how long you’ve been together.

Flirty Text Templates You Can Use Right Now

Feelin’ stuck? Here are some flirty text templates you can copy and make your own:

“You know, if you keep bein’ this cute, I’m gonna have to start flirtin’ with you a whole lot more.”

“Guess who’s thinkin’ about you right now? (Hint: It’s me 😉).”

“So, do you always make people this curious, or am I just special?”

Final Thoughts (And a Little Southern Nudge)

Flirtin’ over text doesn’t have to be a chore. Just keep it light, fun, and remember—you’ve got this. The next time you’re sittin’ there wonderin’ what to text him, use these tips and just be yourself. Confidence is the secret ingredient, after all.

And if you want more tips on flirtin’, dating, or just surviving the crazy world of single mom life, sign up for my newsletter. I send out weekly advice that’s real, relatable, and maybe even a little funny. We’re all in this together, y’all!


Need more flirty text ideas or dating advice? Join our newsletter, and I’ll send tips, tricks, and a little Southern humor straight to your inbox!

Until next time, y’all take care of yourselves, keep things light and fun, and don’t forget to add a little sweetness to everything you do. Life’s too short not to flirt a little.

Catch y’all later!
— April D. Long 💛

About the author

What do you think about the article you've just read? Please tell me below.

This site uses Akismet to reduce spam. Learn how your comment data is processed.

Latest Posts

  • The Art of Keeping Things Casual Without Losing Her Interest

    The Art of Keeping Things Casual Without Losing Her Interest

    Maintain her interest in a casual relationship with these key tips. From low-key outings to playful boundaries, discover how to keep things fun, exciting, and drama-free. Master the art of casual dating with the Friends With Benefits system.

    Read more

  • How to Set Boundaries in a Casual Relationship Without Killing the Vibe

    How to Set Boundaries in a Casual Relationship Without Killing the Vibe

    Keep your casual relationship fun and pressure-free by setting clear boundaries. Learn how to balance time, communication, and emotions to avoid misunderstandings and build mutual respect. Mastering boundaries can make all the difference in casual dating—explore more with the Friends With Benefits system.

    Read more

  • 3 Casual Dating Tips for Men You Must Know

    3 Casual Dating Tips for Men You Must Know

    Avoid the pitfalls of casual dating with three essential tips for success. Learn how to set boundaries, communicate openly, and keep things light and enjoyable. Ready to master the art of casual connections? Discover the full guide with the Friends With Benefits system.

    Read more

Subscribe to Chi Rho Dating

Subscribe now to keep reading and get access to the full archive that consists of more than 1,200 articles.

Continue reading