The First 5 Messages That Actually Get a Reply

You matched. Nice. Now what?

This is the part where a lot of guys crash and burn. You either send a boring “Hey” that goes nowhere, try a cheesy pickup line you found on TikTok, or overthink so much you end up never sending anything at all.

The truth is, most first messages fail because they’re generic. If she’s getting 10 other “Hey, what’s up?” messages that day, yours is going to blend in. The goal is to stand out, and the easiest way to do that is to make your opener personal, specific, and easy to respond to.

First 5 Messages That Actually Get a Reply

Here are five types of first messages that actually get a reply, with examples you can steal and tweak for your own matches.

The Profile Callback

Why it works
You’re showing that you paid attention and didn’t just swipe without looking. It also makes the conversation feel natural from the start.

Example

“You’ve been to Japan twice? Which city should I visit first?”
“You play guitar, what’s the hardest song you’ve learned?”
“Cute dog. What’s their name? They look like a troublemaker.”
“Okay, I need to know where that beach photo was taken. It looks unreal.”

Pro tip
Pick something from their profile or pictures that genuinely interests you. People can tell when you’re forcing it.

The Playful Tease

Why it works
It creates instant chemistry without being over-the-top. The key is keeping it light and friendly, not mean or condescending.

Example

“You’re wearing a Yankees hat in your pic… we might have to discuss this rivalry.”
“You seem active and fit, but there’s no gym pics…suspicious.”
“Okay, so you love to travel, but are we talking Bali or just Miami once a year?”
“Dog mom, huh? Guess I’ll have to win over your pup before I win you over.”

Pro tip
Make sure the tease is something they’d find funny, not personal or sensitive.

The Hypothetical Question

Why it works
It’s fun, unexpected, and gets them thinking. Hypotheticals are conversation starters that go beyond small talk.

Example

“You can teleport anywhere for dinner tonight, where are we going?”
“Someone just made a movie about your life, what’s the title?”
“You get to swap lives with any celebrity for a week, who are you picking?”
“You can only listen to one artist for the rest of your life, who are we stuck with?”

Pro tip
Pick something playful or adventurous rather than heavy or awkward.

The Shared Interest Kickoff

Why it works
You’re immediately bonding over something you both like, which makes continuing the conversation easier.

Example

“You like hiking? I just found a trail with the best sunset view. Have you been?”
“You’re into streetwear, what’s your go-to sneaker?”
“You gym? What’s your lazy day workout when you don’t feel like going?”
“You like cooking? What’s your signature dish when you’re trying to impress someone?”

Pro tip
Mention the shared interest and then add a question so they have something to answer.

The Bold Invite

Why it works
Sometimes confidence is the best opener. You’re skipping small talk and going straight to showing your intentions, but in a casual way.

Example

“We should get coffee this weekend. You free Saturday, around noon?”
“I know a great taco spot. Can I take you to try it?”
“Let me buy you one drink, and if it’s awkward, we can both walk out the bar like it never happened.”
“I’ve got an open seat at brunch this weekend. Should I save it for you?”

Pro tip
Save this for matches where you’ve already had a small back-and-forth, or if your profiles are obviously compatible.

Common Mistakes That Kill Your First Message

Leading with “Hey” or “Hi” and nothing else

It’s the digital equivalent of a blank stare. A single “hey” doesn’t give them anything to respond to, so the conversation dies before it starts. If you’re going to message first, make it count. Ask about something from their profile, crack a small joke, or say why you swiped. Anything beats a one-word greeting that looks like it was sent out of boredom.

Copy-pasting the same opener to everyone

People can tell when your message is generic. If you’re using the same “So what brings you on here?” to every match, it feels lazy and unoriginal. Take ten seconds to personalize it. Mention something from their photos or bio. A small detail, like their dog, trip, or hobby, instantly sets you apart from the copy-paste crowd.

Starting with something overly sexual

Confidence is good. Creepy is not. Jumping straight into flirty or sexual territory before you’ve even said hello comes across as disrespectful and usually earns you an instant unmatch. Keep it fun, light, and respectful. You can be flirty without being gross. Think playful curiosity, not explicit comments.

Writing a paragraph before they’ve replied once

You’re excited, and that’s fine. But dropping an essay as your first message screams “too much, too soon.” The first message should feel effortless, not like a dating resume. Keep it short enough to be easy to reply to and leave room for back-and-forth. Mystery is way more attractive than a life story in paragraph one.

Asking overly personal or negative questions right away

Starting off with “Why are you single?” or “What happened in your last relationship?” instantly kills the vibe. Dating apps are supposed to be fun, not a therapy session. Avoid questions that feel invasive or heavy. Stick to light, interesting topics like travel, music, food, or funny hypotheticals, and save the deep dives for when there’s actual rapport.

The Follow-Up Rule

If they don’t reply within 24 hours, you can send one light follow-up. Keep it playful, not needy.

Example:

“Guess I’ll take that as a no. Maybe some other time.”
“Alright, I’ll assume you got abducted by aliens. I’ll wait for the update.”
“I’ll take the silence as a mysterious vibe. Respect.”
“Did I fail the vibe check already?”

If they still don’t answer after that, move on. Energy is better spent on matches who actually want to talk.

Final Thoughts

A good opener is not about being the funniest or most charming guy on the app. It’s about being intentional. Show that you noticed something about their profile, make it easy for them to reply, and set the tone for a fun conversation.

Get this part right, and your matches will turn into real conversations… and eventually, actual dates.

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