How to Flirt with Guys

#1 More Conversation Starters
"I like your [shoes / bracelet / jacket]—where did you get that?"
Simple compliment. Great for neutral environments. Easy for him to reply to.
"Sorry, random question. You seem like the type who never skips [gym / dessert / Sunday naps]. Am I right?"
Playful assumption with room for correction or jokes.
"You strike me as someone who thinks pineapple belongs on pizza. Prove me wrong."
Fun opener that sparks a playful debate. Good for teasing.
"Are you always this [chill / competitive / mysterious] or is this just a Tuesday thing?"
Soft compliment that leads into personal traits. Works almost anytime.
"Okay, serious question—are you secretly famous or just giving off main character energy?"
Trendy phrase. Teasing and flattering.
"Did you just laugh at that? Now I have to know what your sense of humor is like."
Jump on a shared moment or reaction. Great for bonding through shared experience.
"Hey, do you ever stop being effortlessly charming, or is that just your thing now?"
Charming compliment. Implies attraction while sounding casual.
"Hey. I need to settle a debate. Are you more of a [morning guy / cat person / winter person]?"
Framed as a “mission” but it’s a door to a real talk and shared preferences.
"Hey. Can I ask your opinion on something dumb but important?"
Safe, effective starter. He’ll usually lean in to help and it builds rapport.
"I was just about to say something clever, but now I’m distracted. That’s on you."
Flirt disguised as banter. Slightly bold but fun and disarming.
"You know you walk like someone who’s been in a fight… did you win?"
Flirty teasing with masculine energy. Works well with athletic or confident guys.
"Did you seriously just [do something impressive]? That’s actually kind of hot."
React to something he does and call it out. Honest and confident flirt.
"Be honest: do you practice looking that confident or is it natural?"
Flirty and bold. Most men enjoy being called out in this way if it's lighthearted.
"You look like you know things. What’s the best [movie / series / restaurant] right now?"
Boosts his ego and invites him to talk. Great neutral ground to flirt from.
"Hey. Are you always this focused or are you just trying to look impressive today?"
Playful teasing that flatters. Great for catching his attention in a lighthearted way.
"You’re smiling at your phone. Should I be jealous or is it just a meme?"
Reacting to his behavior and opening up space for a personal or funny answer.
"(Accidentally bump into him) Oh wow—sorry! I should watch where I’m going… unless that was fate."
Funny and flirty. Physical proximity makes it natural. Lets him respond with a smile or tease back.
"How come I’ve never seen you [smile / this dressed up / lose at anything]?"
Notice something different and call it out with charm.
"Is that [watch / cologne / shirt] new or are you just trying to get compliments today?"
Fun and suggestive. Opens space to flirt if he’s responsive.
"Hey. I just realized I’ve never asked—what would you do if you won the lottery today?"
Unexpected opener. Light, creative, and encourages playful conversation.
"I swear you always have this look like you’re up to something. True or false?"
Flirty accusation. Makes him explain himself in a fun way.
"Be honest—how many [pushups / coffees / girls] did you impress today?"
Flirty and teasing. Great with confident or cocky guys who enjoy the attention.
Difficulty Score
50%