‘Bittersweet romantic comedy’? Um, yes. But it’s also intelligent.
Kissing Jessica Stein is up there with Chasing Amy in terms of mature, intelligent and funny examinations of hetero and homosexuality, and how in most cases there is no definite line separating the two, but more of a sliding scale. There are also no gratuitous lesbian love scenes made for the titillation of heterosexual men, so all those guys that used to hire videos from the shop I worked in would be disappointed. (As they often were when they hired films such as Romance, mistakenly thinking that the sex scenes would be erotic).
The film’s denouement also was quite a realistic approach to the situation, and although it’s likely to annoy many people, it does ring true on quite a few levels. There was only a small part of the ending that pissed me off to no end (and it loses half a point for that), but you’ll have to figure out for yourself what that is.