It's interesting how time creates perspective. 1970s fashion wasn't intended to be ridiculous, but it looks so today.
Likewise, THE POMPATUS OF LOVE is a cultural artifact of the 1990s, a piece of fluff from the decade after the Cold War and before 9/11, when the economy was great and Monica Lewinsky's semen-stained dress was the height of political scandal.
In such a relatively carefree decade, THE POMPATUS OF LOVE must have seemed smart and weighty, but today it's a good example of the worst of 1990s petty self-absorption. (TV's SEINFELD was likewise gripped with trivial self-absorption, but at least SEINFELD is hilarious.)
As other reviewers have noted, THE POMPATUS OF LOVE doesn't really have a story. Rather, it's a group of thirtysomething guys who hang out in bars and strip clubs, trading stories about their love lives, advising each other on the mysteries of women and relationships. Between their discussions, we intercut with scenes from their love (or loveless) lives.
Their observations are trite and very old. For instance, there's the guy who's too nice, and thus can't hold onto women. Why-oh-why do women not appreciate nice guys? he laments. (For another 1990s film with this theme, see NICE GUYS SLEEP ALONE.)
There's the immature writer who drove away his lady love, because she wanted more stability. There's the married man who wonders if he should cheat around. There's the ladies man who can't commit.
Some of the women, too, offer their observations (or rather, their ramblings -- one woman admits she both wants, and doesn't want, to know about a guy's past loves, and she admits this makes no sense, but that's how she feels nonetheless).
The film meanders about like this. It's very typical 1990s indie film territory (albeit scrapings from the barrel, rather then the best of indie films). It tries to make up for its lack of plot structure or characterizations with witty observations. (Like PULP FICTION, but not so witty or inventive).
I got the sense that the characters were trying too hard, always babbling their observations on the "war between the sexes" like they were offering new insights. These men sounded like college kids, not thirtysomething guys (although, I suppose, it's all part of that 1990s petty self-absorption).
Since 9/11 and the economic meltdown of 2008, many of these 1990s quirky indie films look trite in retrospect. One might enjoy their innocence, but a lot of them won't age well -- and that certainly includes THE POMPATUS OF LOVE.
(Of course, there are some weighty 1990s indie films that hold up well -- AMERICAN JOB, HENRY FOOL, CLOCKWATCHERS, THE HOUSE OF YES.)

