I'm trying to identify a movie I watched as a teenager on Italian TV in the early 2000s (so the film was likely made in the late 1990s or possibly early 2000s).
Here's everything I remember:
Set in New York City, with a Woody Allen-ish feel (but I don't think it was actually directed by or starring Woody Allen)
The male lead was short, bald, and not conventionally attractive
The female lead was brunette and more attractive than him
They were in a relationship that she considered perfect
In one key scene — an argument/fight — she tells him that they are perfect together, and she knows this because she has had several previous relationships (she mentions a specific number, something like 6 or 7 ex-boyfriends, but I'm not sure of the exact number). She tells him something like "when you've had as many relationships as I have, you'll understand how perfect we are together"
Despite this, he breaks up with her
There are then scenes of him with other women and her with other men
It seems like at some point he comes back to her, but I don't clearly remember the ending
The tone was ironic and bittersweet
It felt like a low-budget or mid-budget American production, the kind that would air on late-night TV
Any ideas? I've been trying to figure this out for years!