Flirting on Social Media with a Girl: What Dating Pros Recommend

Dating Coach Julianne Cantarella on the do’s & don’ts of flirting with women online

Co-authored by Julianne Cantarella and Kyle Hall

Last Updated: January 28, 2026 Fact Checked

Flirting with girls on social media can feel just as anxiety-inducing as doing it IRL. What do you say first? How do you avoid coming on too strong or creeping her out? We’re happy to tell you that the secret to success isn’t some super complicated system you have to follow. By going in with the right mindset and keeping a few tips in mind, you’ve totally got this. To help you feel even more confident, we talked to dating pros to get their best tips for flirting with women online, including what to avoid. Check out their advice below!

How to Flirt with a Girl over Social Media

Dating coach Julianne Cantarella says to read a girl’s profile before trying to flirt with her on social media. Then, you can bring up something interesting about her, like one of her hobbies or a thing you have in common, which is way more likely to get her attention than a generic “Hey, you’re so pretty” message. Here are some other pro tips:

Keep your tone lighthearted and fun.
Use occasional emojis for a playful vibe.
Like a few of her photos to show you’re interested, but not too many.
Drop flirty hints that you’re into her.
Ask her on a date if the vibes are good so the conversation doesn’t stall.

1

Check out her interests on her profile before starting a chat.

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“You want to show that you've read her profile,” says dating coach Julianne Cantarella. That way, “when you reach out to her, you [can] indicate something that was in her profile that spoke to you.”^{[1]
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Expert Source

Julianne Cantarella
Dating & Relationship Coach

Expert Interview} This accomplishes two things: It kicks off your conversation smoothly, and it makes it less likely that you come across as someone just playing the field and messaging a lot of girls at once (which can be an instant turn-off).

Meet the wikiHow Experts

Julianne Cantarella is a dating coach and the CEO and President of New Jersey's Matchmaker. She has over a decade of experience helping people heal from heartbreak and find healthy, long-term love.

Shana Tibi is a certified professional matchmaker and the Founder of Curated Connections, a matchmaking service for single professionals. She specializes in understanding core values and personal preferences to curate dates.

Renee Slansky is a dating coach and global dating advisor to several of the largest online publications and dating platforms in the world. In addition to offering one-on-one coaching, Renee has produced courses to help both men and women gain clarity, confidence, and direction with their love life.

Cher Gopman is a dating coach and the Founder of NYC Wingwoman LLC, a date coaching service based in New York City. She has been featured on Inside Edition, Fox, ABC, VH1, and The New York Post.

Cristina Morara is a dating coach and the Founder of Stellar Hitch Private Matchmaking, a luxury matchmaking service based in Los Angeles. As a former casting director, Cristina specializes in finding the perfect partner through her exclusive global network and detailed, warm approach.

2

Message her about something besides her looks.

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Most girls want you to like them for something other than just their appearance. Messaging a girl that she’s beautiful probably won’t get you far if she’s used to getting messages like that, so stand out by being more specific. “Specific is terrific; it's a funny little rhyme, but it's true. You want to pick something specific and approach them about that,” says certified professional matchmaker Shana Tibi.^{[2]
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Shana Tibi
Certified Professional Matchmaker

Expert Interview} For example, if she went hiking in Italy last month, you could say something like, “Hey! How’s it going? I saw your pics of the Cinque Terre trails. It looks so beautiful there. My friends and I are actually considering doing a hiking trip in Italy this summer.”
- In the same vein, definitely don’t start with a single-word “Hey” or “Hi” message. "Nobody, man or woman, likes ‘Hi.’ It doesn't leave room for anything and is usually a deal breaker for most people. So be specific,” says Tibi.^{[3]
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  Shana Tibi
  Certified Professional Matchmaker
  
  Expert Interview}

3

Keep your messages lighthearted and fun.

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The goal is to flirt and have fun, not be overly serious right off the bat. "Keep it light. Keep it fun,” recommends dating coach Renee Slansky. “If you try to go into full [seduction] mode, it could come across really cheesy or too sexual.”^{[4]
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Renee Slansky
Dating Coach

Expert Interview} Cantarella agrees. “You want to use humor. Women always find humor attractive.”^{[5]
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Julianne Cantarella
Dating & Relationship Coach

Expert Interview}
- Think, witty and silly banter (I might die of boredom at work. Please save me with a mildly interesting thing that happened to you today) rather than cheesy jokes or one-liners (Do you have a map? Because I just got lost in your eyes). Here are some good examples to get a sense of the vibe you should be going for:
  - “Darn, you’re a Mets fan? How is it cheering for the second-best MLB team in NY? 😉”
  - “I just saw the biggest spider in my kitchen, and now I won’t be able to ever cook in there again. Pls send help?”
  - “What’s one of your biggest hot takes? Mine is that mullets are amazing and I’m glad they’re making a comeback 💁‍♂️”
  - “I’m embarrassed to admit I’ve never surfed before. Should I try it? You make it look easy, but I’m pretty clumsy…”

4

Like some of her photos, but don’t go overboard.

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"There's no harm in liking a few photos,” says dating and relationship coach Christina Jay, NLP. “But I wouldn't bombard someone's page with hearts and whatnot. You don't want to scare them off, so use [likes] diligently."^{[6]
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Christina Jay, NLP
Dating & Relationship Coach

Expert Interview} Start by liking maybe 2 or 3 of her photos, preferably ones where she’s doing something particularly fun or interesting (at the dog park with her cute dog, celebrating her birthday with friends, etc.). Once you’ve been messaging and she posts new photos, you can always like those ones, too (just avoid liking every new photo she posts).

5

Use emojis, but sparingly.

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Emojis help keep things fun and playful, but too many can be a turn-off. Dating coach Cher Gopman encourages the use of emojis when flirting online. “You do want to use a little bit of [emojis] just to show that it's lighthearted and fun,” she says. However, she cautions against overdoing it: “You don't want to overuse them, because that'll come off as too eager.”^{[7]
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Cher Gopman
Dating Coach

Expert Interview}
- A good rule of thumb? Use emojis as often as you typically do when messaging your friends. That way, you’re being authentic to your typical messaging style.
- That said, if you never use emojis when messaging, don’t be afraid to throw in an occasional 😉, 👀, or 👻 to keep the conversation playful.
- If you normally use a lot of emojis with your friends (like at least one in every single message), maybe dial it back with the girl you’re messaging, at least for now.
- Good example: “My cat destroyed the laces on my nice shoes. I think he’s upset that I went to dinner with friends without him 😜” — This hits the sweet spot. It feels playful without going overboard.

6

Make your intentions clear as things progress.

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Don’t be afraid to let on that you’re interested in her romantically. Tibi warns that keeping your cards too close to your chest can actually backfire. "Being too subtle is a little like, ‘Well, does he really like me?’” she says.^{[8]
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Shana Tibi
Certified Professional Matchmaker

Expert Interview} If you’ve been exchanging messages and the vibe seems good, put yourself out there and make it clear that you’re into her. This might look something like:
- “Brains and beauty? So you’re basically the entire package 😅” — This makes it clear that you’re attracted to her.
- “I’ve never attempted pottery but kind of want to give it a shot…Romantic pottery class date in our future?” — This alludes to a potential future date.
- “I woke up still thinking about our conversation yesterday. I like talking to you 😊” — This shows that you’re thinking about her and want to keep connecting.

7

Ask her to hang out IRL if you’re feeling a connection.

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Once you’ve established a flirty connection, it’s time to ask for a date. Flirting on social media is fun, but you don’t want things to stall and fizzle. Keep the spark going by asking her to hang out. “Glean what she's interested in and grab it and run with it,” says dating coach Cristina Morara, who recommends saying something like, “There's this really cool vegan restaurant that just opened up on Abbot Kinney, I'd love to take you there, would you like to go on Friday night, seven o'clock?”^{[9]
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Cristina Morara
Dating Coach

Expert Interview}
- Just how long should you wait before asking for a date? “It's usually best to have at least five exchanges back and forth before asking for the date,” says Gopman.^{[10]
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  Cher Gopman
  Dating Coach
  
  Expert Interview}

8

Keep the flirting going if your date goes well.

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If things went well, this is a great time to grow your connection and continue showing her that you’re into her. Here’s what Gopman recommends: “Don't be afraid to send a photo of somewhere that you're at that's interesting… Or say a song just came on and that reminded you of [her]. You can say, ‘Hey, I'm listening to this song and it made me think of you!’” Keep liking some of her posts and photos on social media, too. The goal is to keep the good vibes going!^{[11]
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Cher Gopman
Dating Coach

Expert Interview}