Riding with someone slower: Sit on their wheel for 2-3 hours and chat, bust out a head and find a nice spot for lunch regroup. Ride the afternoon alone. On a headwind day just plop them in my 63cm bike + 4 bag bowshock.

When riding with someone at the same level we usually just trade drafts. On the hills splits occur with a regroup on the next flat. Ride some days separate.

Riding with three. Never -ever- leave one person at the back even on climbs.

Only ridden once with someone who could insta drop me thank goodness his GF was along and we were at the same level. He pulled 60% of the time with me and GF splitting the other.