How to Flirt with Guys
#2 Conversation Options
Back to Conversation Starters. Explore more Tools for Talking to Men.
"Have you always been this confident or is it recent?"
Signals that you’re observing him closely. Invites stories and light self-praise.
"Okay, now I need to know—how do you stay so chill all the time?"
Complimenting his demeanor invites him to reveal more about himself.
"You look like you're plotting something. Should I be worried?"
Silly, cheeky way to create flirtatious curiosity.
"What do you usually do when you’re not being effortlessly [cool]?"
Light teasing with a compliment. Keep it casual.
"You really know how to [dress]. Do you get compliments all the time?"
Flirty and flattering. Works for appearance-conscious men. Use anything from [dress] to [smell].
"You have a great voice. Has anyone told you that?"
Slightly risky but flattering. Unexpected compliments work well.
"What’s your type? Wait—actually don’t tell me… unless it’s me."
Obvious flirtation. High risk, high reward. Best used if rapport is already strong.
"That thing you said earlier—was that meant to be funny or are you just naturally charming?"
Flirt disguised as confusion. A clever way to bring humor into the conversation.
"You seem like you know exactly what you want. Is that true or just good acting?"
Creates playful tension. Invites him to open up.
"You always have this calm energy. What's your secret?"
Subtle compliment that opens space for him to talk about himself. Works well with thoughtful guys.
"I still haven’t figured you out. Are you always this mysterious?"
Creates intrigue. Keeps the focus on him while signaling playful interest.
"Do you always smile like that or am I just lucky today?"
Flirty, but disarming. Makes him feel noticed in a playful way.