Planning a Reunion Trip When Nobody Lives in the Same City Anymore

Every group has this trip. The one that's been "definitely happening" since a conversation two years ago, that resurfaces every few months, gets four enthusiastic replies and then goes quiet again. Nobody's lost interest. It just never crosses the line from idea to booking.

Reunion trips stall for a specific reason: everyone now lives somewhere different, so there's no default. No shared calendar, no obvious destination, no local who knows the place. Every single decision has to be made from scratch, and nothing ever gets written down where the whole group can see it.

Dates first, and offer options rather than asking

"When's everyone free?" is what kills these trips. Six people answer vaguely, nobody commits, and the thread dies. Pick two or three specific windows yourself and ask people to choose one. A forced choice gets a real answer in a day; an open question gets "probably most of October?"

Set a reply deadline and say what happens if someone misses it. A group of five that books beats a group of eight that never does.

Pick somewhere nobody's an expert

This feels like a disadvantage and isn't. When nobody knows the destination, everyone researches a bit and contributes something — which spreads the work and means the trip isn't just one person's version of the place. Throw everything into a shared list and by the time you land you've got a real shortlist rather than one person's half-finished tabs.

Get the plan out of the group chat immediately

The chat is where reunion trips go to die. Anything you agree on scrolls away within the hour, so the same three questions get asked every few weeks and the trip never feels real enough for anyone to book a flight.

The fix is one shared plan with a single link — dates, accommodation, the shape of the weekend — that everyone can open and edit. That's exactly what bothways does: the moment the dates and the outline exist somewhere permanent, the trip stops being an idea and people start booking.

Six cities means six arrivals, and that's your hardest day

When everyone's flying in from somewhere different, Friday night is where the plan lives or dies. Add each flight and look at the arrivals together, with live status, so the first evening is built around when people actually land rather than the times they quoted you in March.

• One named meeting point — a specific bar, not "the hotel"
• A rule for early arrivals: wait, or go ahead and check in
• A plan for whoever's flight is delayed, decided before it is

Don't reopen settled decisions

Once the dates and destination are agreed, they're agreed. Someone will float a better idea in month three. Reopening a settled decision resets the whole thing to zero, and that's how a trip ends up in year three of being definitely happening.

Fix the dates, write it down somewhere everyone can see, and let the group fill it in. That's genuinely most of it.