Writer by the lead actresses Heather Juergensen and Jennifer Westfeldt, Kissing Jessica Stein is a bright, low-budget NYC set rom-com with a lesbian slant. Jessica Stein (Westfeldt) is a career-driven girl who finds herself unexpectedly in love with Helen Cooper (Juergensen); having never imagined herself as a lesbian, Jessica struggles with the disapproval of her Jewish family, and her own expectation that she needs a man in her life. Westfelt has since gone on to success as an actress (in 24) and writer (Friends with Kids), but it’s a shame that neither performer has returned to this kind of indie fare. Although some have found the ending a cop-out, Kissing Jessica Stein is more about coming out of your shell and challenging stereotypes rather than dividing matters along sexual battle-lines; both girl shine in this lightweight but effective comedy.
It’s a sweet movie that doesn’t really try and make itself all about the whole lesbian-angle. And much rather, about how this woman really just wants to fall in love and be loved by whomever she can find to be her perfect someone. Good review.