How to Be Playful over Text

Co-authored by Cristina Morara and Hannah Madden

Last Updated: September 3, 2021 References

If you’re texting your crush or someone you like, you might try to be a little playful. Getting playful and flirty is a great way to build interest and let them know that you like them. We’ve compiled some of the best ways you can keep your conversation going with a little good-natured fun and flirty texts so you’ll never run out of things to say!

1

Ask a flirty question.

Everyone likes to talk about themselves. Get a playful conversation going with a pointed question, like:^{[1]
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- “Do you like it when someone makes the first move?”
- “If I were to take you on a date, where would you want to go?”

2

Debate a playful topic.

You can get a little heated (in a flirty way). Bring up something a little controversial, like:^{[2]
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- “Pineapple on pizza: yes or no?”
- “Cats or dogs?”
- “Hamburgers or hot dogs?”

3

Send a picture of a goofy animal.

Then say, “This reminded me of you.” It will let them know that you’re thinking about them, but it will also tease them a little bit.^{[3]
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- Look for a baby animal making a silly face or an animal tripping over its own feet for extra comedic value.

4

Get a competition going.

There’s nothing better than a little schoolyard fun! Playfully ask the person you’re texting to compete with you by saying something like:^{[4]
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- “Whoever can make the other person laugh the hardest wins. GO!”
- “I bet I can text back faster than you can.”

5

Ask them to save you from a boring situation.

Make them the hero of your story with a simple question. If you have an event, class, or meeting that’s going to be excruciating to sit through, see if they can entertain you by saying:^{[5]
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- “Ugh, I have this super boring assembly to go to today. Will you text me to make it more fun?”
- “URGENT: Need distractions. This meeting will never end.”

6

See if they miss you.

Get them thinking about the next time you’ll see each other. You can make sure you’re on their mind by saying something like:^{[6]
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- “Do you miss me yet?”
- “I bet you miss me already, huh?”
- “Looking forward to our next date?”

7

Tell them your favorite things for your next date.

Flowers, candy, and chocolates set the tone for a date. You can tell the person you’re texting what kind of gifts to get you if they want to woo you. For example:^{[7]
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- “In case you’re wondering, my favorite flowers are roses and I love Hershey’s chocolate.”
- “If you were thinking about buying me flowers, you should go for daffodils.”

8

Playfully tease them a little bit.

Playful humor can go a long way. Pick out one of their quirks and make fun of it, but don’t get too mean! Throw in a few “lol”s or “haha”s if you need to tone it down. For example:^{[8]
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- (If they have a complicated coffee order) “Don’t forget to ask for whipped cream made from tiny unicorns! lol”
- (If they’re always running late) “Fashionably late again? Haha.”

9

Tell them you’re thinking about them.

It’ll make them feel good and let them know that you care. You can do it in a playful way so you don’t seem so serious, like:^{[9]
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- “I have so much to do, but I keep getting distracted by you.”
- “I’m trying to fall asleep but you keep running through my mind.”

10

Set up a time for your next date.

Don’t be afraid to get a little bold. The more playful you are, the more lighthearted and fun it will feel. For example:^{[10]
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- “We should probably go on another date soon.”
- “You’re going to love the outfit I wear on our next date.”
- “Any room for me in your weekend plans?”

Expert Q&A

Question

Is it okay to tease a boy I like over text to get his attention?

Cristina Morara
Dating Coach
Cristina Morara is a Professional Matchmaker, Dating Coach, Relationship Expert, and the Founder of Stellar Hitch Private Matchmaking, a luxury matchmaking service based in Los Angeles that serves clients nationwide and internationally. As a former casting director, Cristina specializes in finding the perfect partner through her exclusive global network and detailed, warm approach. Cristina holds a BA in Communications and Psychology from Villanova University. Stellar Hitch has been featured in the Huffington Post, Chelsea Handler’s Netflix documentary, ABC News, the Tonight Show, Voyage LA, and the Celebrity Perspective.

Cristina Morara

Dating Coach

Expert Answer

Sure, a little bit of flirty teasing is a fine way to pique his interests! Just make sure that you don't overdo it, and ready your texts carefully before you send them. It's pretty hard to communicate sarcasm or playful teasing over text, so don't send anything that may be misinterpreted.
Question

What can I do if he occasionally texts me inappropriate things? I want him to like me, but he just goes over the top sometimes.

Cristina Morara
Dating Coach
Cristina Morara is a Professional Matchmaker, Dating Coach, Relationship Expert, and the Founder of Stellar Hitch Private Matchmaking, a luxury matchmaking service based in Los Angeles that serves clients nationwide and internationally. As a former casting director, Cristina specializes in finding the perfect partner through her exclusive global network and detailed, warm approach. Cristina holds a BA in Communications and Psychology from Villanova University. Stellar Hitch has been featured in the Huffington Post, Chelsea Handler’s Netflix documentary, ABC News, the Tonight Show, Voyage LA, and the Celebrity Perspective.

Cristina Morara

Dating Coach

Expert Answer

Be firm and tell him to stop it with the inappropriate texts. That's it. If he doesn't listen to you on this one, cut contact off entirely. You may not be happy with that, but it's best to avoid people who can't respect your boundaries.