Flirting online isn’t about cheesy pickup lines or trying too hard to be someone you’re not. It’s about confidence, curiosity, and showing genuine interest. If you’re wondering how to flirt with a woman on dating apps and actually build a connection, you’re already ahead of most. That curiosity is a great start.
In this guide, you’ll learn how to flirt in a way that feels natural and respectful, so you can stand out for all the right reasons.
1. Start with a Personalized Opener
Skip the “Hey” or “Hi, beautiful.” A generic message tells her you’re not putting in effort, and it’s probably what she sees 20 times a day.
Instead, look at her profile and open with something specific:
“You said you love hiking—what’s your favorite trail so far?”
Personalized messages show that you took time to read her profile. That effort alone can set a flirty tone because it feels thoughtful and intentional.
Need help writing an engaging opener? Tools like ChatGPT’s dating profile assistant can help brainstorm creative ideas.
2. Compliment Her—But Be Real
A good flirt isn’t all compliments, but a well-placed one makes a big impact. Focus on things that feel sincere and slightly unexpected:
“You have such a great laugh—it totally comes through in your photos.”
Compliments about confidence, style, or personality land better than comments only about looks. Women get judged on appearance constantly—flirting with depth shows you’re different.
If you’re dating on a plus-size friendly app like WooPlus, you’re already in a space where women feel safer and more seen. That’s the perfect foundation for more confident, respectful flirting.
3. Match Her Energy and Tone
If she’s being playful, flirt right back. If she’s more chill or witty, adjust your style to match. The key is mirroring without mimicking. Good flirtation feels like a dance, not a performance.
Here’s a tip: if she gives you one-word answers or dry responses, she may not be interested. Respect that. But if she’s responding quickly, asking questions, and teasing back? You’re in.
4. Add a Little Humor
Don’t try to be a stand-up comedian, but a little humor lightens the vibe.
Instead of:
“What are you doing this weekend?”
Try:
“So be honest… do you actually hike, or is it just a profile photo flex?”
This kind of teasing—if delivered warmly—creates instant chemistry. Just make sure it’s never at her expense. Avoid sarcasm or comments that could be misunderstood.
5. Know When to Switch Platforms
Once the flirting is mutual and you’ve built trust, suggest moving the conversation to another platform like Instagram or text. But always ask respectfully:
“You’ve been great to talk to—would you feel comfortable continuing this on IG or text?”
Pressuring someone too early can kill the vibe. Timing matters.
6. Don’t Overthink It—Just Be You
Sometimes flirting goes wrong when you try too hard to be someone you’re not. The most attractive quality? Authenticity.
You’re not here to impress her with a script. You’re here to connect. Flirting should feel like a fun interaction, not a job interview.
7. Be Playful, But Respectful
You can absolutely flirt and still be respectful. Ask her what excites her, what makes her laugh, what her dream weekend looks like. Show curiosity in who she is, not just how she looks.
If you’re worried about crossing a line, here’s a rule of thumb: if you wouldn’t say it to someone in person you barely know, don’t type it either.
8. Use Emojis Tastefully
A wink or laughing emoji can soften your message and make it feel more flirtatious. But don’t go overboard—use emojis to enhance your tone, not replace your words.
9. Know When to Flirt, and When to Just Talk
Some moments aren’t about flirting. Maybe she’s telling you about a tough day or her family. That’s your cue to shift gears and just listen. A thoughtful response shows emotional intelligence, which is a major flirt move in disguise.
“That sounds really stressful. I’m glad you shared that.”
Empathy is attractive. Women remember how you made them feel more than anything you say.
10. Ask for the Date Confidently
Once the chemistry is real, go for it:
“I’ve really enjoyed chatting with you. Would you want to grab a coffee this weekend?”
Flirting is fun, but the end goal is connection. Don’t let a great match fizzle because you hesitated.
Final Thoughts
Flirting with a woman on dating apps isn’t about being slick—it’s about being genuine, playful, and respectful. Stay curious, be kind, and most importantly, enjoy the process.
And if you’re looking for a space where plus-size women and their admirers feel truly welcome, WooPlus is the app you need to try. It’s a body-positive community built for real connection, not unrealistic standards.
Ready to flirt with confidence? Start swiping smarter.
