How to Chat with Guys Online
#1 More Conversation Starters
"Can I confess something? I don’t usually message first… but your [profile / photo] caught me."
Makes him feel chosen. Vulnerability works if you deliver it with confidence.
"I need a verdict: [sushi] on a first date. Overdone or elite move?"
Engaging scenario-based question that feels conversational.
"Hey, quick question: what’s your go-to comfort food?"
Warm and personal. Everyone has an answer.
"Hey. I saw you mention [dogs / whiskey / your favorite band] and I had to ask—are you as into it as you sound?"
Target a shared interest or passion. Direct and warm.
"I was going to just like your profile and keep scrolling, but I had questions."
Mysterious and confident. High reward with the right tone.
"This is random, but you look like someone who gives great hugs."
Unexpected, kind, and slightly flirty. Great way to make him smile.
"You seem like the kind of guy who gives really good music recommendations. True or false?"
Indirect compliment. Flirty and opens up a music exchange.
"You’re smiling in almost every pic. What’s got you in such a good mood?"
Observational. Starts soft and gives him something personal to share.
"I feel like you’d be the fun one at a boring wedding. Am I wrong?"
Funny, slightly flirty assumption. Invites him to share stories or personality.
"Hi. Be honest—did you write your bio in five minutes or actually think about it?"
Joking tone, lightly challenging. Gets past the boring intros.
"Okay, serious question: is that really your [pet / car / guitar], or are you just borrowing it for likes?"
Playful challenge based on something in his profile. Light teasing with high reply potential.
"You have "good at trivia but humble about it" energy. Am I close?"
Niche compliment. Unique openers like this stand out.
"I saw your travel pic and instantly got wanderlust. Where was that taken?"
Easy opener when his profile shows travel. Natural, low pressure.
"Hey. I had to say—your [photo with the dog / travel pic / cooking post] made me smile."
Start by noticing something specific in his profile. Genuine, non-threatening, and flattering.
"Wait… are you the type who actually replies to messages? Just trying to set expectations here."
Funny and meta. Self-aware tone works well on dating apps.
"Hey. You seem like someone who’s either really into [coffee / sports / hiking] or secretly hates it."
Playful profiling. Sets up shared interests or surprises.
"Okay, weird question: do you believe in second chances or just great timing?"
Softly deep. Works if his vibe seems thoughtful or romantic.
"Okay, you look like you have a strong meme game. True or just photogenic confidence?"
Funny and lighthearted. Appeals to most modern online users.
"You seem dangerously charming. I’m trying to figure out if that’s a red flag or not."
Teasing flirt. Suggests interest but keeps her in control.
"Hey. I bet you’ve got strong opinions about [pineapple on pizza / hot takes]. Wanna test that theory?"
Light, fun, and opens a debate—perfect for sparking chat.
"Alright, I’m taking bets—are you a [cat guy / gym guy / board game nerd] or did I get that totally wrong?"
Make a bold guess. If wrong, it still sparks curiosity.
"You look like the guy who says "I don’t watch TV" but secretly binges crime docs."
Playful personality guess. Easy opener for a fun back-and-forth.
"Okay, mystery man. Your profile is 60% charm and 40% sarcasm. Is that accurate?"
Interpret something in his vibe. High chance of playful denial or confirmation.
"Alright, I have to ask. What's the story behind that [tattoo / shirt / photo]?"
Shows curiosity. Low-risk and makes him feel interesting.