Dating texting guide

What to say when a guy texts you hey?

What to say when a guy texts you just 'hey', and how to turn a bare greeting into a real conversation without over-explaining or going cold.

Read the situation

A bare "hey" is the lowest-effort opener there is. It tells you he wants to start something but hasn't decided what, and it gives you nothing to react to. That is the whole problem. You are not being asked a question, so any reply that sits there waiting for him to do the work will quietly hand the conversation back to him, and he may just say "hey" again.

What a good reply does is give him something specific to answer. It doesn't have to be clever or flirtatious. It has to be easy to respond to and show that you're glad he wrote. Short, warm, and carrying a small hook is enough.

The mistake most people make is treating a "hey" as a test of their wit. It isn't. It's an opening move, and the job is to keep the door open without making a speech about it.

A boring opener next to the reply WingAI writes instead
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A bare hey tells you very little

A single "hey" with nothing after it is ambiguous. It could mean he's bored, he's checking if you're still around, he's got a little interest and wants to see what you do, or he sent it to three people. You can't tell which from the word alone, so don't try to guess his full intent. Look at the context you do have: how long it's been since you last talked, whether the previous conversation ended warmly, what time it is, and whether he's sent anything else. Those tell you how much weight to put on it.

Read it as a low-commitment opener. He has put a small amount of effort in and left the next move with you. A reply that matches that effort, meaning warm and short but with something in it, tells him the door is open. A reply that over-invests tells him you're more interested than he's shown, which can make the next message feel heavy for him.

Give him something specific to answer

Two or three kinds of reply work here. The first is a light return that mirrors his energy and adds one small detail about your day, a thing that just happened or something you're looking at. It should be easy to answer with a sentence and leave a loose thread he can pull. You can tell a draft is this kind because it contains a fact about you and nothing that requires him to do anything.

The second is a reply that asks something open but low-stakes, like a question about what he's up to, where he is, or what he's watching. The question should be easy to answer in one line. Leave out anything heavy, anything that asks him to explain his intentions, and anything that works as a quiz.

The third is a playful reply that teases the bareness of the message itself. It works when the two of you already have some banter, and it should be short enough to read as a joke, not a comment on his effort. Leave out anything that sounds like criticism or that makes him defend the greeting.

Reply in daylight, not at 2am

Timing changes how a "hey" lands. If he sends it at a normal hour and you reply within a few hours, the exchange feels like two people catching up. If he sends it late at night and you reply the next afternoon, it feels casual and often slips away. Neither is a rule, but matching the rhythm of your replies to his usually works better than an instant reply every time.

If you don't answer within the day, send one short message later rather than leaving it. If he doesn't reply to your reply within a couple of days, let it go. Don't send a second "hey" to check whether he's still there. Stopping at a single follow-up keeps the exchange light, and it protects you from spending energy on someone who was only passing time.

Do not send

Why these replies fail

  • “hey! sorry I took so long to reply, I've been swamped with work and then I fell asleep on the couch lol”

    The apology and the long backstory make a simple greeting feel like a debt you owe him.

  • “hey”

    Sending the same bare word back gives him nothing to answer, so the thread stalls.

  • “Hi! Are you free this weekend? We should definitely grab coffee sometime.”

    A plan request this early asks him for a commitment he hasn't signalled, and it skips the conversation entirely.

Avoid these

Common mistakes

  • Replying with just "hey" back and letting the silence do the rest
  • Writing a long paragraph that reads like you've been waiting all day
  • Asking a flat yes-or-no question that closes the thread
  • Ignoring the greeting and jumping straight into a complaint or a logistics question
  • Answering a "hey" at 2am with the same energy as a planned conversation

Questions people ask

Is it bad to reply to a hey with just hey?
It isn't wrong, but it usually stops the conversation. A bare greeting back leaves him to decide what happens next, and most people won't do that work if they weren't already invested. If you want the exchange to continue, add one small thing you can both build on, like a detail about your day or an easy question about his.
Should I wait a while before replying to a hey?
You don't need to play games. Replying within a few hours during the day is fine. If it's late at night, a reply the next day reads as normal. What matters more is that your reply has substance, so the timing doesn't carry more meaning than it should.
What if he only ever sends hey and nothing more?
Pay attention to the pattern. If the bare greetings keep arriving and never turn into anything, he may be keeping options open or just passing time. Give it a few exchanges. If the conversation still doesn't grow, you can stop replying without making a point of it.
Can a hey turn into a real conversation?
Yes, if the reply gives him something to respond to and he follows through. A small detail or an easy question is usually enough to move from greeting to chat. Watch whether his replies get longer and whether he starts asking you things. Those are good signs the conversation is moving.

What people say after using WingAI

  • “I was skeptical at first. Then I tried it on a dry chat and the replies actually sounded like me, not a chatbot.”

    Mazoonx

  • “I always freeze on the first sentence. This gets me past that blank box so I actually hit send.”

    joejoe4567

  • “She went cold mid-week and I had no idea what to say. The reply I sent felt natural and she picked the chat back up.”

    Marcus T.

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