What to do if he reschedules four times in one month

One reschedule tells you almost nothing. Four in a month tells you how plans with you rank against whatever else is fighting for his evenings. Look at how each change arrived. If he gave notice a few hours before, that's a different signal than someone who moved things a week out with a new day already in mind. Then look at what he offered next. Vague stuff like we should do something soon usually means he hasn't decided. A specific alternative means he still wants to see you and just has a conflict.

Also check whether the reasons keep changing or keep repeating. Work stress that never lets up is still a pattern. You're really checking whether his effort to rebook matches his effort to cancel.

Stop accepting open ended replies. A message that asks for a specific slot forces him either to commit or to show you where he stands. Propose a day and time, or offer two options and let him pick. That puts the planning back on him, which is where it belongs.

Keep the tone flat and warm. You're not asking him to explain himself, and you're not reading out a list of past changes. One light mention that this is the fourth change is enough. The person who keeps moving things is the one who owes an explanation anyway. If you want a real talk about it, save that for in person, so it doesn't land as a verdict over text.

Give him one clear window to respond. If he doesn't answer your concrete proposal within a day or so, one follow up is fair, something as simple as checking whether the slot works. Don't send a third or fourth message chasing him. Silence after a specific ask tells you something, and chasing it makes you the only one doing the planning.

Stop offering new dates once he has moved the same plan twice. At that point it's no longer about scheduling. Let the next move come from him, and don't fill the gap with reassurance texts while you wait. If nothing gets rebooked after about two weeks of quiet, treat the plans as paused and get on with your month.