Flirting: A Quick-Start Guide
Estimated reading time: 4 minutes
I’d like the suggest that flirting is not something you have to master — that’s like trying to go pro at golf when you’re barely able to mini-golf.
Instead, start where you are (say, “Level 1”) and work your way up (“Level 2”, then “Level 3” and so on).
In previous articles, I proposed a new definition of flirting (“engaging someone with warmth, humor, and curiosity — sometimes with a hint of attraction, always with respect.”) and explored the common concerns that hold people back from flirting.
This article is about how to stop overthinking and actually start flirting.
Most people believe they need to feel confident before they flirt, or that it only “counts” if it leads to something. But flirting isn’t a test you pass or fail. It’s a social skill. And like any skill, we all start out as bumbling beginners. You practice, get feedback, tweak things, and try again.
A Simple Framework
1. Be Friendly
A genuine smile and eye contact go a long way in signaling friendliness
Flirting starts with friendliness. That usually means:
Making eye contact (yes, even if you're shy)
Smile (the Duchenne kind where your eyes squint a little)
Being present (aka staring into space or at your phone)
This alone already separates you from 90% of people who feel awkward in social settings. Friendliness signals “I’m open to interaction” without saying a word.
2. Show Curiosity
Instead of sticking to polite small talk, advance the conversation with something a bit more personal.
Try:
“Is that your go-to drink?”
“How did you get into that?”
“Have you always been into [topic they just mentioned]?”
Skip:
“What’s your biggest fear?”
“How’s your relationship with your parents?”
You’re not trying (nor want to) to get emotional intimacy five minutes into a new conversation. Just nudge it into something slightly more interesting than weather or work.
3. Add Playfulness
Playfulness doesn’t mean being clever or funny. It just means adding a touch of energy or amusement.
Examples:
“You seem way too confident. I bet you're terrible at trivia.”
“Did you dress up to outshine the rest of us?”
“I bet you picked the best item on the menu and now I have to guess what it is.”
Think of it like seasoning a dish — a little goes a long way. And if you overdo it? Well, you’ll learn and do better the next time.
4. Watch for Feedback
Flirting isn’t a solo sport. Is it feeling like a tennis rally? Or more like you’re lobbing balls into the void?
Good signs:
They’re smiling, laughing, and making eye contact
They tease back or ask questions
They linger a little
Not-so-good signs:
They give one-word answers
They’re looking around
Their body is turned away
They seem distracted or disinterested
You won’t be able to read minds, but you’ll likely notice (or learn to notice) if something isn’t mutual. Adjust accordingly and try not to take it personally.
Speaking of which…
5. Stay Unattached to the Outcome
This might be the hardest part.
Flirting doesn’t have to lead anywhere. View it less like a transaction, and more like an invitation or check-in:
“Is this connection fun? Do we enjoy this back-and-forth?”
You’ll also build confidence by doing (bonus: confidence is attractive!).
Recognizing Flirting
Body language cues like leaning in, smiling, and mirroring can signal mutual interest
Curious whether someone might be flirting with you?
Watch for signals like:
Holding eye contact a second or two longer
Smiling and laughing as you talk
Mirroring your posture or gestures
Leaning in slightly
Inviting you to share more (e.g, “Tell me more about that.”)
Referring to potential or future plans (e.g., “Invite me next time!”)
Relating to you (e.g., “I like that, too!”)
Teasing you (e.g., “You’re definitely trying to impress me with that answer.”)
Be careful not to use this as a checklist. These are heuristics to help you pay attention for mutual interest, so your miles may vary.
Flirting Is a Skill Worth Building
Like any skill, flirting gets easier and more natural with practice over time
Do you remember when you first started learning a new skill?
Sports, dancing, drawing, public speaking — whatever it was, you probably weren’t very good on day one. But if you stuck with it and practiced intentionally, things got better and easier.
Eventually, you stopped noticing the awkwardness. Or at least, it didn’t stop you.
Same goes for flirting. You won’t become smooth overnight. You can, however, learn how to flirt poorly overnight. All part of the process.
Smile. Say hi. Wave. Ask a playful question. Tease gently.
Flirting is one of the best ways to create sparks of connection in everyday life.
