How to Start a Conversation With a Guy Over Text: 25 Openers That Beat "Hey"

Why "hey, how are you" doesn't work

Imagine someone you barely know texts you: "Hey." Now you have to figure out why they're writing, come up with a topic and somehow not seem boring. Most people answer just as briefly: "Hey. Good. You?" And the conversation runs out of air by message three.

Same with guys. It's not that he doesn't want to talk. You just didn't give him anything to grab onto.

Three checks for your first message

1. He doesn't have to come up with a topic. The topic is already in your message: the party where you met, the dog in his photo, a debate about the best show of the year.
2. It has a detail. Not "do you like to travel?" but "is that Teriberka in the photo? Did you really swim in the Barents Sea?" (that's a remote village on Russia's Arctic coast, and the water is freezing).
3. It can't be answered with "yes" or "no." A "how" or "why" question gets a real answer. "Do you like…?" gets one word.

If your message passes all three checks, length barely matters. Still, two or three sentences is best. A long first message reads like a letter that needs an equally long reply.

25 first messages for different situations

These are templates, not copy-paste texts. Swap in your own details. A guy can tell when a message wasn't written for him.

You met in person

1. Pick the debate back up"Okay, I checked: pineapple pizza was invented in Canada, not Italy. So you were half wrong."
2. Bring back a moment"So how did the story about the cat stuck on your neighbor's balcony end? I never got to hear it."
3. Hold him to a promise"You said you know the café with the best pancakes in town. Name, please, or I won't believe you."
4. Own the awkwardness"I spent all evening trying to remember the band you told me about. I give up, help me out."
5. Ask for advice"You're the only one of us who knows bikes. I've got a 4-mile commute through the city, what should I get?"

A match on a dating app

1. A detail from his photo"Is your third photo in the Altai mountains? I've been planning a trip for three years and can't pick a route."
2. A line from his profile"You wrote that you make the best pilaf in the neighborhood. Challenge accepted, my dad's Uzbek."
3. A this-or-that question"Your profile has both mountains and the beach. If vacation started tomorrow, which one?"
4. Your own opinion"I see Interstellar in your favorites. Unpopular opinion: I didn't like the ending. Change my mind."
5. A game"Two truths and a lie, guess: I've been skydiving, I'm scared of pigeons, I won the school chemistry olympiad."

More games like this that you can play right in the chat are in texting games.

You haven't talked in a while

1. Something that happened"Drove past our old school, there's a shawarma place there now. Remembered how you used to hide your gym shoes there."
2. Something you found"Found a photo on my phone from that rafting trip where you fell off the catamaran. Want it?"
3. A question about his thing"Heard you opened your own workshop. How's being your own boss? Just like the memes?"
4. An honest opener"Haven't texted in forever, but today I heard the song we listened to on the way to the beach. How are you?"
5. Advice"You're still into gaming, right? I want to get my brother a console without going broke, help?"

After a first date

1. An echo of the evening"Checked when I got home: that waiter really did have a "trainee" badge. You called it."
2. Straightforward"I had a really good time. Let's do it again, but this time I pick the place."
3. Continue the topic"Watched the trailer for that movie you told me about. It looks weird. I love it."
4. A joke from the night"I dreamed about the pigeon that tried to steal your croissant. He'll be back."
5. A plan"You said you've never been ice skating. The rink opens Saturday, want to fix that?"

Replying to a story or post

1. Ask about the place"Where is that sunset? I want to go this weekend."
2. Ask about the process"Did you build that table yourself? How many times did you want to give up?"
3. Your own story"My cat sleeps in a vacuum box exactly like that. Nobody cares about the vacuum, by the way."
4. Ask him to settle a bet"My friend and I are arguing whether this photo is from a concert or a rehearsal. Who wins?"
5. Reaction plus a question"You read Pelevin? (Russian cult novelist, for the uninitiated.) Which book should I start with so I don't quit on page ten?"

What kills a conversation at the start

• "Hey" and then silence. He replied "hey," and now you're both waiting. Send the greeting and the hook in one message.
• Three questions in a row. He'll answer only the last one, and the rest get lost. One question at a time.
• "Sorry to bother you." There's nothing to apologize for. You didn't break any rules, and apologizing immediately puts you a step down.
• "Why aren't you answering?" an hour later. He could be driving, at the gym, in a meeting. Guilt-tripping kills any desire to reply at all.
• A wall of text. Five paragraphs as a first message demand the same from him. Easier to put it off and forget.

He replied: how not to fumble the second move

The second message is where things most often fall apart. He replied, you got excited and asked a new, unrelated question. It's better to pick up a detail from his answer. He writes: "Went to the Altai last year, hiked to Belukha" (the highest peak in Siberia). Bad: "Cool! What else are you into?" Good: "Belukha? That's almost a week on foot. What was the hardest part?"

Add a bit about yourself so it doesn't turn into an interview. A couple of his answers, then one of your stories. If the chat still slides into "yeah" and "I see," read what to do about awkward silence, and topics for the weeks ahead are in what to talk about with your boyfriend.

If you're always the one starting things and his replies are dry every time, don't spend a month on it. Three or four tries with good hooks are enough to tell he doesn't have the interest or the time right now.

Rehearse on a character

A first message is easier to write once you've seen how different people react to different openers. On my-idol.ru you can try starting a conversation with a man of few words, with a wry type who answers a question with a question, and with a cocky smart-mouth. Mistakes cost nothing there: if it doesn't land, start over and see what changes. It's practice, not a replacement for real people, but afterward "hey" no longer feels like your only option.

If you want your message to come across as a little flirty rather than just friendly, that's covered in how to get him interested over text.