'Shaking the Tree' follows a long trend of the 20-something soul searching story which involves a group of friends longing for the glory days and wondering what exactly went wrong in life that they didn't quite achieve what they thought they could have. Faded sports heroes, lost loves, deadend jobs, and sometimes nothing at all. The earliest of these and probably the most recognized is 'Diner' and later, 'The Big Chill' and 'St. Elmo's Fire.' Others that I can think of is the early 90s 'Queens Logic' and the late 90s comedy, 'The Four Aces.' 'Shaking the Tree,' because it offers nothing new really, and even stories of characters that are not all that unique or really all that interesting compared to others like it, it is instantly forgettable, despite the nostalgic appeal of 80s regular, Ayre Gross and pre-Friends Courtney Cox.
This is simply the story of four guys long past their own glory days. One is soon-to-be-father and aspiring novelist who can't seem to relate to his wife and deals with it by fooling around. Another is engaged to be married, but wedding plans are nixed when he finds out that his fiancée long ago slept with one of his friends. Another is a bartender who can't box anymore and is wondering what is left for him. And another comes from money but has zero ambition and, seems to deal with that, by running away from everything except for the ten grand bet he gambled away at the races.
Not a particularly bad movie. A nice distracting time waster, if nothing else, but overall, there are a slew of this variety of comedy/dramas that have been in the past 20 years alone, and this one is nothing special among them.