With his father (Sydney Pollack) a marring man he is on his sixth wife at the beginning and number seven turns up later in the film we can understand why Tom (Patrick Dempsey) is shy of commitment. But he is more than ready to take on a new lover when ever the opportunity arises.
As the film progresses we know tom must make a choice of life-style all forced upon him by Hannah (Michelle Monaghan) who is his best friend and his obvious life partner. The first half of the film revolves around his love affairs and the comfort zone between the two stars.
His life style might be the envy of many, great looking girls jumping at the opportunity to be intimate, he is as popular as many might like to be. But he can't curl up with a quick short lived lover, when he needs a girl who is a friend it's Hannah. It takes most of the film for him to come to that realization, we figure it out in the first scene. While we contemplate the foundation for a life together, is it based on a sound friendship or a quick sparkling flash. Tom doesn't care. Life is very comfortable he has the best of both worlds.
Hannah on the other hand wants more. Once she becomes involved with a Scottish Colin McMurray (Kevin McKidd) and he offers marriage into a family in which he is a Duke, has a castle, plenty of money and wants a permanent relationship the playing field for Tom is drastically altered.
The comfort of the relationship early on is pleasant to observe and even the activity preparing for the wedding before they fly to Scotland has its moments. Dads number six wife offers very warm motherly advice, a size 8 dress on a size 16 body bring some humor as does a shower scene with the new fiance.
Kathleen Quinlan graces the wedding preparations with knowing glances as Hannah's mother. She is part of the emotion which carries us through an interesting happy relationship between Tom and Hannah.
But the positive emotion and fun is lost when the story moves to the wedding location in Scotland. There everything falls apart. The film becomes part of Four Weddings and a Funeral, or My Best Friend's Wedding, silly games are played as the two men attempt to compete with each other, and contrived situations drive the intended lovers apart. Tom is held down in bed by his former blond lover just as Hannah enters the room, leading to the conclusion that he's up to his old tricks again.
What begins as a comfortable romp of attraction and a non permanent alliance, looses itself in a silly ending at the foot of Reverend Foote (James Sikking) when Tom crashes the wedding calling to Hannah almost as
Dustin Hoffman did in The Graduate, but sadly the imagination of that film is not present here.