How long to wait before asking if he still wants to meet

A single late reply means very little. What matters is the shape over several days. If he was sending messages with substance and now he's sending short replies a few hours apart, the energy has dropped. If he has stopped suggesting anything for the next time, that's a second signal. If he still responds warmly when you do message but never picks up a thread, he may be interested but disorganised, or he may be keeping things open without committing.

Look at whether he initiated at all during the quiet stretch. People who are interested tend to reach out first at least some of the time, even briefly. Someone who only ever answers, and never starts, is giving you a clear read on how much effort he's putting in. That doesn't mean he doesn't like you, but it does mean you shouldn't carry the whole plan alone.

If the plan was for a specific day and that day is close, the silence is more concerning than if it's three weeks away with nothing set. A missing confirmation for something happening tomorrow is worth a check-in. A missing reply to a vague "we should get a drink sometime" is much less of a signal.

The check-in works best when it's a small, concrete question with a clear yes or no. Something that refers to the plan you already made, names the day or time, and asks whether it still stands. You're not asking him to explain his feelings. You're asking him to confirm a logistic. That lowers the pressure on him and gives you a usable answer.

Avoid burying the question inside a long message about your own week, or wrapping it in apologies for asking. Both make it sound like you're bracing for rejection, and they make his reply feel like it carries more weight than it should. Keep your tone relaxed and assume the plan is still possible until he tells you otherwise.

If he gives you a vague answer, something like "maybe, I'll let you know," you can accept that once and suggest a concrete alternative with a deadline, such as "no worries, let me know by Sunday and we can pick something else." That gives him an easy exit or an easy yes, and it stops the loop.

Send the check-in once, then give it a reasonable window. For a plan within the next day or two, a few hours is fair. For something further out, a day is enough before you can reasonably ask again. If there's still nothing, a single short follow-up is acceptable, but make it clearly lighter and don't pile on new information or new questions.

If you get no reply after two attempts across a couple of days, treat that as an answer. Don't keep the thread alive by hoping. Stop initiating, let the conversation rest, and see whether he comes back on his own. If he does, respond warmly without bringing up the gap. If he doesn't, the decision has been made for you, and you can move on without needing a dramatic conversation.

When he does reply after a long gap with something vague or noncommittal, you're allowed to say what you need. A short "I'd like to see you, so let me know if that's something you want" is a clear, adult way to close the loop. It leaves the choice with him and keeps your position visible.