What to say when he keeps asking how your day is going

This text is the conversational equivalent of saying 'I want to talk to you but I'm not sure how.' He's either nervous, or he hasn't thought about you enough to come up with anything specific. Neither is a deal breaker yet. What matters is whether he'll actually shift gears when you give him a real opening.

Repetition over days or weeks shows a pattern. He's comfortable texting you but hasn't moved toward asking you out or digging into anything real. That's the diagnosis. He's in a holding pattern.

Your reply should be short and friendly, but it should contain one specific detail or opinion about your day. Not a novel. Just something actual. Then, without asking him a generic question back, you point toward something that could matter. It could be a comment on something he said before, a reference to plans, or a light observation that invites him to step up.

The goal is to show you're engaged and real, not robotic. Don't reward low effort with high effort. Match his tone but raise the bar for what the next message should do.

If he's asked 'how's your day' three times in a week and hasn't mentioned hanging out or asked anything that shows he's paying attention to who you are, you've got room for one or two more replies like this before a pattern is set. After that, shorter answers or longer gaps between responses start making sense.

If weeks go by and this is all the conversation is, stop replying to the loop the same way. A dry reply or no reply sends the message that this approach isn't working. He'll either step up or fade, and both outcomes are clearer than the stalled conversation.