Men Share Their Best Dating Conversation Starters

Men Share Their Best Dating Conversation Starters

Dating can be hard. You find someone you like, gain the courage to walk up to them and… what do you do next? What do you say? How do you make your encounter memorable? How do you hold their interest? The answer, according to men, is pretty much unanimous: You don’t need to say much. Below, men of the Internet reveal the best dating conversation starters. Next time you’re stuck for something to say to your crush, try one of these.

Don’t forget to check the comment section below the article for more interesting stories!

#1 Smile and Ask

Smile. Ask if you can join me. Then get up and walk away after realizing your mistake.

#2 Talk About Everyone’s Favorite Person

Married guy here with three kids. Let’s assume the conversation is not necessarily intended to be romantic. Maybe you’re the only two people watching gymnastics practice or something. If there’s any kind of shared activity you can’t go wrong commenting on it to the guy (works both ways) like, “Wow, they have really improved this year,” or something. Easy peasy for any kind sport/activity with kids involved.

However, let’s say kids were not involved and maybe there is some actual intent to flirt/get to know a possible person to ask on a date. I remember being single and being blown away when a woman would initiate conversation. So much depended on the context. At a party with mutual friends, it was easy: “So how do you know Bob and Jenny? I’m Mary by the way.” It’s a very disarming conversation starter and gives you an “in.”

And always remember who everyone’s favorite person to talk about is: themselves. Ask questions and then actually shut up and listen. Add some commentary along the way, but let them speak. Really what I am saying above is just go read Dale Carnegie’s books. That guy knew some stuff about communication that holds true decades later.

#3 Literally Anything

Literally anything. Guys will talk to a tree if it talks first.

#4 Just Have Him Listen

I feel sorry for anyone, man or woman, who tries to start a conversation with me. My mind goes blank when I speak with new people. I can give only the most obvious, terse answers to anything. It would be better if the woman simply wanted someone to listen to her and not seek a real conversation.

#5 Hi

I dated a girl for a little while. She just walked up to me and “Hi.”

#6 Ask Him to Hang Out

When I was in college I was hanging out in the lounge of my dorm when this girl that lived there walked past with a pizza. She said to me, “Hey I just got this pizza and I can’t finish it all myself. Want to help me eat it and watch House in my room?” I found this girl attractive and the offer of free pizza was just an added benefit for me. It was definitely the best conversation starter/pickup line I have had used on me.

#7 Hey


#8 Pretend You’re Not Nervous

Just pretend it’s someone you aren’t nervous to talk to. How do you talk to a customer at work? A group member in school? A cashier at the store? Starting a conversation isn’t hard, it’s just the anxiety behind having an interest in the person. Start out simple and move forward from there. You can do it!

#9 Don’t Insult

As long as you’re not insulting us, you’re golden.

#10 Ask Him if He’s Single

Compliments work. Ask us about our interests. If you want to make it clear you’re interested, ask us if we’re single. If we’re wearing a band shirt, ask us about it, even if you’re not familiar with the band, ask us what we like about it and what we’d recommend you listening to. If you really want to make an impression, don’t be afraid to be a little random/weird.

#11 Bionicle Collections

“You wanna see my Bionicle collection?”

#12 Any of These Questions

People (or women in this case) should be able to categorize their interests and then find common ground systematically by probing with questions such as:

“You play any video games?” If yes, ask for videos, about the learning curve, ranking system, funny character customization.

“What are you studying/did you study?” Followed by asking what kind of companies could you work for, but which ones do you dream of working for?

“Do you try to stay active?” If they seem like the type, followed by a workout routine/sports schedule.

“What car would you buy with 80k?”

“What’s the most you’ve drunk in one night?” (Again judge by type, most people will have an answer)

“What’s the farthest you’ve traveled from here?” – Last resort #1

“Do you like to make memes?” – Last resort #2

“Do you think Epstein killed himself?” – Last resort #3

“I’m looking for a deep, long-lasting commitment in a very short time, what are you looking for?” – Alternatively for making a conversation as short as possible.

“Do you have any spare change?” – To get out of a conversation altogether.

#13 Ask for Help with Something

Ask us for help with something. We will almost always say yes no matter if we know what we’re doing or not.

#14 Offer Snacks

This girl walked into class on the first day of the semester like five minutes late. One of the only seats open was right by me, so she sat down, got settled, then pulled out some Runts and said, “Hey you can have some of these as long as don’t effing take the bananas.” I basically spent the whole semester hung up on her, so if that was her intention, b’gawd it worked.

#15 A Compliment

A compliment is a good way to start. It gets our attention and it’s not often we get compliments; especially from the opposite sex.

#16 Ask for Help

I think the best way, in my opinion, is to ask for “help”. Not a damsel in distress help. But let’s say you’re at a bar or coffee shop. Just a simple “Hey, do you know what the cross street is here?” I saw another answer about a girl offering pizza. But she said, “Hey, I can’t eat all this, think you could come help me?” It’s an easy-open invitation to interact and engage.

Guys very typically like helping/problem-solving. At the very least you’ll get an answer to that icebreaker of a question, an easy let down if they aren’t interested “sorry I don’t” (goes back to doing what they’re doing) or someone interested but doesn’t know the answer and they’ll go out of their way to find the answer because they want to provide it for you.

Once they’re talking it can easily move into further conversation “oh thanks, you’re a lifesaver, do you come here often?” type of stuff.

#17 Something Silly

She noticed me on her first day of work. She started with a “boo” after clumsily stomping down the stairwell that she knew I was working by, hoping to startle me. We just got married two months ago.

#18 Whatever He’s Interested In

If you have an inkling of something the guy is interested in, ask him about it (possibly prepare to get your ear talked off). Bonus points if you know anything- more about the subject. If the guy’s a blank slate, ask about something popular at that moment in time. Use memes as a quick reference. Today it would likely be about baby Yoda for example.

#19 Can’t Go Wrong with a Classic

Hey, how are you?

#20 They’re Oblivious

Two weeks ago I was in my elevator on the way up to my apartment. A girl came in and complimented my umbrella. Spoilers my umbrella was a plain black shitty umbrella. She was like, “Nice umbrella! It looks so cute, where did you get it?!” I’m like, uh the terrible department store down the street. She’s like, “Oh good to know… lookin’ good.” Kept smiling at me, looking in my eyes. Then brushed my arm and said, “Hopefully I’ll see ya around,” as I got off the elevator.

I was like damn! That woman was really nice! She wasn’t talking about my umbrella. I’m an idiot.  Girls if you’re gonna even try with a guy, we’re so oblivious, you have to be really damn obvious. My lightbulb didn’t turn on until I told my best female friend about this nice girl on the elevator.

#21 Men Don’t Care

None of us care/will remember how it starts. As soon as we’re aware you’re talking to us, we’re just trying not to say something dumb or just grab you and pet you too hard like Lenny from Of Mice and Men. It’s quite the tightrope, actually.

#22 Call His Attention

Something more than “Hey, how are you?” because to me it’s so common to just pass someone in the store and say hey as a polite thing that it doesn’t catch my attention. You literally have to stop and say something. Call my attention to something like if I’m at the store ask about something I’ll stop and try to answer it. Something where it’s not the usual pleasantries.

#23 History Lesson

“Hey I’m _____. Don’t you agree Trebuchets are the superior siege weapon?”

#24 We’re All People

Don’t think of it as guy vs girl. Instead, we are all just people. And you start conversations the same way with any person.

#25 Please Talk to Me

A girl in a bar a few weeks ago just sat right down next to me, put her hand on my shoulder, and said: “Please talk to me.” 110% worked flawlessly. That’s the level of creativity you need.

#26 Compliment, Introduce, Question

C.I.Q – compliment, introduce, question

This works both ways round, so everyone can use it.


  1. I really like your shoes. My names is [insert name]. Where could I buy some of those as a gift for my mum/dad/sister/brother (make it someone in the family)?

  2. You smell amazing. I’ve never smelt that aftershave before. My name is [insert name]. What are you wearing?

  3. You look like you’re having a really great time and I couldn’t help but notice your smile. My name is [insert name]. What are you celebrating?

The process immediately gets someone on your side, then reduces the awkwardness and breaks the ice about who you are, making the other person feel a little more at ease, then elicits a response to a perfectly legitimate and related question to begin the two-way interaction. I’ve never had this technique fail on me.

#27 Find Something in Common

Find something in common whether it be whats on their shirt or what they’re doing like drawing etc. If not just start with whatever’s going on around you.

#28 What’s Your Favorite Marsupial?

Disclaimer: not a man. But when I was on Bumble I’d always start the conversation with “What’s your favorite marsupial?” So I could tell if they were on my level of weird. It’s how I started the first convo I ever had with my SO. Almost two years later and we’re weird together now.

#29 Just Something Weird

The weirder the better.

#30 Bees Shouldn’t be Able to Fly

“According to all known laws of aviation, there is no way that a bee should be able to fly. Its wings are too small to get its fat little body off the ground. The bee, of course, flies anyways. Because bees don’t care what humans think is impossible.”

#31 Most Guys are Attention-Hungry

It literally doesn’t matter, most guys are so attention-hungry from girls that we would appreciate anything. Just try to tap into either of your interests.

#32 Be Prepared to Have a Conversation

The same way you’d like a guy to start a conversation with you. I think the harder part for women is what comes after. I’ve had girls chat me up and I didn’t realize until after the fact because they didn’t really lead the conversation anywhere. Like they’d say one thing and expect me to do the rest, meanwhile, I’m sitting here thinking “She’s just being polite” or “She’s literally just asking for an answer to this question.” It doesn’t even occur to me that maybe I should start flirting or something, so I respond and leave it. And when I do read it right it feels like they turn it around as if I chatted them first and I need to put in all the effort to make the conversation go, which is a big turn off. So I’d say start a conversation however you want, but be prepared to actually have a conversation. Part of that also includes not bailing the second the chat isn’t flowing super easy.

#33 “Hi”


#34 A Compliment

Start with a compliment.

#35 Just “Hey”

“Hey there, handsome.” “Ma’am this is a Wendy’s.”

#36 Coffee

“Do you want coffee?” I will ALWAYS say yes, NO MATTER WHAT. Even if I have a fresh cup in my hand. Even if I am making a cup. I will say yes in all instances. Yes, I have a coffee problem That problem? That I don’t have enough coffee.

#37 What He Likes

Ask him what he likes.

#38 Talk About Deserts

Whatever really. My girlfriend started the first conversation we ever had talking about deserts. Funnily enough, I was mildly annoyed at the time because I was really itching to get back to the book I’d been reading and she chose that time to randomly start chatting. Really glad she did, though.

#39 What’s Up?

A genuine smile and a “What’s up?” Gets me every time.

#40 Dumb Questions

If you prefer straightforward: “Hey you’re cute and I wanted to say hello before I leave. Let’s exchange numbers/Facebook accounts” Less straightforward: “Hi, my name is __.” Then he will probably give you his name. If he doesn’t, ask him. If he doesn’t tell you, conversation over. Then if he doesn’t continue after giving his name say literally anything. An example would be “What do you do for work?” Or, “Do you like sports/videogames/going to music festivals?” “Where did you go to school?” “Where did you grow up?” “Do you like Japanese food?” “Favorite marvel superhero?”

You can always say something off the wall to see if they have a decent sense of humor. Like “Hey if you had to place a bet on it, who would win, a tiger or a gorilla?” Guys love questions like that. My friends literally debated this for hours.

#41 What Are You Reading?

“What are you reading there?” Works best with physical books, kind of creepy if I’m reading on my phone, though.

#42 Doesn’t Matter What

Anything please it doesn’t matter because it’s exceptional. Cheers.

#43 Say Literally Anything

Just ask a question or say literally anything. We are so pleasantly surprised when a girl initiates conversation.

#44 No Pick-Up Lines

When she just talks to you. Doesn’t even use any pick-up lines or anything cheesy. If it is a genuine conversation.

#45 I Like Your Shirt

A compliment on something simple like “I like your shirt.” Guys don’t get enough compliments already and any time a girl compliments a guy he’ll usually be so flattered he won’t know what to even say.