60 Best Funny And Flirty Text Messages To Make Your Crush Smile

Making your crush smile is a mighty significant achievement. Using flirty text messages wisely can make your crush fall for you. Read to know how.

By DeadLine Writer
60 Best Funny And Flirty Text Messages To Make Your Crush Smile

How to compose flirty text messages to make your crush laugh out loud?

Diane Keaton photographed by Norman Seeff, 1975.

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Laughter is the best route to anybody's heart, and while everyone's sense of humor is different, having some fun questions to ask your crush in your texting bank helps you ease into a comfortable conversational flow. Just keep in mind that the first rule of comedy is timing. Don't put pressure on yourself to seem funny, upbeat, and cute all the time. Ask the questions that feel right, and you'll get your crush to open up over text. Keep it lighthearted, and you'll keep yourself entertained as well as them. You're not just here to make friends — you're also here to have fun.

“First we feel. Then we fall.”

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Having some fun questions to ask your crush also allows you to feel out their sense of humor. Personally, I love being around people who are funnier than I am. If you find yourself texting someone who takes themselves super seriously and who is afraid of joking, then you might see you turn out to be the relationship's clown. That's fine, though. Every comedy duo needs a more serious person. Maybe this crush you're texting will turn out to be yours!

Tips for flirty yet funny text messages conversation

Jane Birkin, 1970s

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Tell Jokes

When you are out with your crush, pick the right moment to tell a joke best. Whether it is one you got from someone else or one you made up yourself, making a girl laugh is the best way to attract her attention and make you seem sexier in her eyes. It can also be the best way to break the ice. Laughing will make you both feel more comfortable, easing the tension that often comes with new relationships.

Fight Knight, US Vogue December 1989
Model Naomi Campbell with Mike Tyson

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~For example, use jokes that play on words. Tell jokes like "What did the duck say when he bought lipstick? Put it on my bill." These kinds of tricks are humorous and are funny to everyone. ~A well-placed knock-knock joke is always a winning idea, and you can make it flirtatious as well. Try something like "'Knock-knock!' 'Who's there?' 'You're.' You're who?' 'You're so cute when you smile.'" It pays her a compliment and will most likely get her to smile. ~Keep your jokes tasteful. You don't want to make the wrong impression by insulting your crush so early in your relationship. Keep them on topics that are appropriate for all types of people. Save the more specialized jokes for when you know her better.

Your Sense of Humor is the Ultimate Weapon

Make funny and seductive comments about the things around you. Maybe, you notice a significant push/pull sign on a door is an overstatement. Make a joke about it, such as "Could that sign be any bigger? I think we get the point.", Then exaggerate your movements as you push the door open. Or maybe pretend the sign is wrong by pretending to pull and acting like it isn't working. It will let her know you are attentive to your surroundings and show her that you can come up with humor on the spot.

Arthur Miller and Marilyn Monroe photographed by Sam Shaw, 1957

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You can also incorporate sarcasm into these types of situations. If you see someone with a large truck, say something like "I think that guy should buy a bigger truck. I hear the prices of Mac trucks are down this year." Dry wit is usually appreciated and will make her laugh. Just make sure you don't only talk in sarcastic remarks. She might think you are a negative person and not want to be around you.

Tease her till Soft Limits

Find small things about her that you can pick on. Make a joke about how large her handbag is or the size of her sunglasses, anything that is small and unimportant. For example, ask her "Plan on robbing a bank later? I think you can use your purse as the getaway car." Remember to keep your tone light and keep a smile on your face. You don't want her to think you are making fun of her.

Poetic Justice, 1993

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~Don't take it too far and hurt her feelings. Stay away from topics like her weight, what she looks like, or other things that might be a sore subject. You don't want to make her think you're mean or cause significant offense so early in your courtship. ~Try making fun of yourself as well. It lets your crush know that you have a sense of humor about yourself and you don't take yourself too seriously. Say something like "I'm a great driver. Today, I even got a note complimenting my skills that said 'Parking Fine.'" Just remember not to take it too far and become too self-deprecating.

Do Impressions

Nothing is better than a great impression to get someone to laugh. Pick a celebrity that you know your crush likes or someone you both know, like a mutual friend or a professor. This way, she won't miss out on the joke and can be laughing along with you.

Make sure you test out your impressions on others before you try to impress your crush. It is apparent that you don't want your crush to be laughing at you because your opinion is so wrong. Right?

Observe how others joke

If you aren't prone to clever jokes, don't worry. There are many different kinds of tricks out there in books, blogs, and videos, so pick some and memorize them. This way, next time you are around your crush, you can tell a great joke, and no one will ever know it wasn't yours.

Observe your crush

When you are first getting to know someone, you may not know what kinds of things that make them laugh. If you don't see your crush that well, try to talk more, you get an idea of interests that the girl you like loves. You can also pay attention to the clothes she wears and items she carries, looking for any reference to shows she may want, topics your crush may be passionate about, or genres of literature, music, movie, or TV shows she may enjoy. These elements will give you a broader idea of the type of humor she enjoys.

How to make your crush smile using flirty text messages

Flirting with your crush is essential when it comes to sparking up a new relationship. Make sure you’re doing it right by asking these questions. When it comes to your crush, you always want to find a way to let them know you’re interested without overkill. A lot of times, people think that flirting should be straight-forward, so the “flirty” gets the hint. However, finding a connection with someone you’re interested in can be much more comfortable when you do it subtly. By making a point to ask your crush questions and get to know them, you’re pointing out how much you like them, but you’re not flirting so much that they feel trapped. Flirting should always be subtle and smooth. Someone once told me that the best way to flirt with someone is to leave them wondering if you’re teasing.

Here are some fun and seductive examples to ask your crush to get yourself off to the right start.

Flirty text message questions that will light the fire within your crush

Some of the best questions to ask your newly found crush are ones that help you get to know them and draw attention to their personal life. These issues will plant the idea that you’re interested and help you find out more about them, their interests, and their tastes. Seductive examples of these questions will help you, big time.

#1 Have you been working out? #2 What are you looking for in a guy? #3 How can someone like you not have a boyfriend? #4 How did you get so attractive? #5 How are you so good at? #6 What would be your ideal date? #7 Why are you so funny? #8 What did you first think of me? #9 What’s the most romantic date you’ve ever been? #10 Who’s your celebrity crush? #11 Who do you think should make the first move? Guys or girls? #12 Would you instead be considered sexy or smart? #13 Are you looking to get a boyfriend/girlfriend anytime soon? #14 What’s the one thing that makes you the happiest? #15 What do you wear to bed—if anything? #16 Would you ever go to a nude beach? #17 What would you do if I told you how attractive you are? #18 What are your favorite pet names? #19 What’s your biggest turn on when dating someone? #20 How would you describe yourself in 3 words?

Flirty text message questions to take your relationship a little farther

Use these examples to a friend you’re comfortable. If things start to get awkward, tone the questions down or move on to a few subtler ones.

#21 Okay, now how would you describe me in 3 words? #22 Are you a butt or a boob guy? Be honest. #23 What’s your favorite feature on a guy/girl? #24 Do you find tattoos sexy? #25 Have you ever been skinny dipping? #26 *If the answer to the previous question is “no”* Would you ever go skinny dipping? #27 Are your parents as good-looking as you? #28 What’s the most embarrassing thing that’s ever happened to you when you were with a significant other? #29 Would you prefer to make out or cuddle? Or make out, then cuddle? #30 If you could have any job in the world, what would it be? #31 Do you prefer a pool or a hot tub? #32 Have you ever had sex on the beach? No. I don’t mean the drink. #33 What’s one thing you would lie about to your boyfriend? #34 What’s the naughtiest thing you’ve ever said to someone? #35 How o you feel about your very first date? #36 What makes you the most nervous?

#37 Would you rather be invisible or have x-ray vision? #38 If you could change one thing about your life right now, what would it be? #39 What room—other than the bedroom—gets you going the most? #40 How about we go out sometime?

Flirty text message questions to spice up the conversation

If you just want to get flirty, use these seductive examples. But if it’s the naughty sexual flirting you want.

#41 If I’m feeling horny when you’re around, do you think you’d realize it? And how do you think you’d recognize the signs? #42 If I caught you feeling yourself in bed, would you blush awkwardly and accept that I picked you, or would you pretend like you were just shifting your butt about on the couch? #43 What’s the meanest thing you’ve ever done to someone to get back to them? #44 When was the first time you had a wet dream? #45 Have you ever played doctor as a child? With whom did you play and how old were you? #46 What is your wildest sexual secret that you want to indulge in at least once in your lifetime? #47 Have you ever been caught naked by someone? #48 Have you ever found something valuable on the street and kept it for yourself even though you knew you could return it to the owner? #49 What is the most embarrassing moment you’ve experienced in your lifetime? #50 Can you tell me your funniest childhood memory that you can remember?

Sarah Jessica Parker hanging out with Robert Downey Jr. in the 1980s

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#51 Personally, do you think size matters in reality? #52 If you had no choice, how many days do you think you could abstain from sex or masturbation at a stretch? #53 What gets you wet faster, phone sex or sexting? #54 While having sex, would you prefer getting on top or staying down in bed? #55 If you had to pick an animal, which animal do you find the sexiest of all? #56 If you had to explain about the birds and the bees to a child, let me hear how you’d go about telling it to them? #57 Who is the most significant jerk/bitch you’ve ever come across in your life and why? #58 Have you ever accidentally and yet intentionally kissed someone or tried kissing someone? #59 When was the last time you scratched yourself down there in public? #60 If the world froze for an afternoon and only you could move, and no one could see you or remember what you did, what would you do?