I’ve rarely used the “Ride With” function successfully there are two issue:
You automatically end up behind the rider you are trying to “ride with” …if they are in the group, you will never catch up unless you bury yourself, which is no fun, even in a race.
If someone is riding “Reverse Watopia”, “Ride with” adds more insult to injury. It will drop you behind the person, going the wrong direction. If they are are a hill, you may not be able to get slow enough to turn around until you get flat enough to drop below 15 mph.