Tried a standing monthly dinner with my two closest buddies over a group chat, and it actually stuck
My two best friends and I used to just text in a group chat that went silent for months at a time, so in January we picked the first Tuesday of each month at a taco place near downtown and made it a standing thing. Six months in and we have not missed one yet, mostly I think because nobody has to be the one to plan it or ask. Has anyone else had luck locking in a set day like that, or does it stop working once someone's schedule changes?
Six months with zero misses at a taco place is partly the tacos, but mostly the fixed spot. Here is the thing nobody brings up: the place itself does half the work. You walk in, the guy behind the counter already knows your order, you sit at the same table, and there is nothing to decide. Start rotating restaurants and suddenly every month has a group chat about where to eat, and that chat is where these things go to die. A standing day only holds if the where is as boring and locked in as the when. Pick one spot you all like enough, never move it, and let the staff watch you get old.
The part about "nobody has to be the one to plan it or ask" is the whole trick honestly. The second you make it a thing someone has to organize every time, it dies. We did the same thing with a Thursday lunch and the one rule that saved it was this: if you can't make it, you just don't come, no guilt, no rescheduling the whole thing for one person. The other two still show up. That keeps it from turning into a group project where everybody's waiting on everybody. The other thing is don't let the day drift, because once you start moving it around to fit schedules it stops feeling locked in and turns back into regular planning. We've had guys miss three in a row and just slide back in when life calms down, which would never happen if we canceled every time someone was out.