I’m trying to find this movie possibly 1990-2000 where a father and his son meet another couple like them, which is a single mother and her single daughter. Both families, dad-son and the mother-daughter are of course unrelated. I don’t remember the motive why either the dad or the mom are single, maybe because they widowed or maybe gone through a divorce, can’t remember.
These couples use to see each other like once in a year for a few years, if I recall because they lived in separated towns.
So, these two couples used to see each other or maybe even double date when the dad and his son visited them until the mom passes away. That’s when the father realizes he didn’t want his son to make the same mistake he did wasting time and never take a step forward in the commitment.
I may be wrong with time span of the movie but the movie theme goes with the description I gave.