Common Sense Note
Parents need to know that this thoughtful romantic comedy about flawed adult characters isn't as clear-cut as many other Hollywood "chick flicks." For that reason, it's likely to resonate more with adults than teens and tweens who haven't gone through complicated relationships yet. Still, the content isn't inappropriate for teens: There's some passionate kissing and a good bit of discussion about sex (including implications of a lesbian college fling and passing mention of a threesome), but nothing graphic; language is mostly on the mild side ("s--t" is only used in one scene, though it carries a lot of weight when it is used); and there's no violence. Several scenes do feature social drinking (a few also show Will drunk) and smoking; one sequence in particular makes sharing a cigarette break seem like a romantic, intimate experience. Divorce is also an issue here; the main character's tween daughter is upset by her parents' impending split and wants them to reconcile.
Sexual
Content
Several scenes of passionate kissing, some of which take place in bed (though characters are never naked). Regular discussion of sex/sex life (or lack thereof); Will's roommate talks about his one-night stand, and Will mentions the possibility of a threesome or foursome at one point (prompting Maya to ask what that is). Characters cheat/stray. Sections from a character's college diary suggest a lesbian fling. TV footage from the Monica Lewinsky scandal. Early scenes show parents of grade schoolers upset because their kids have gotten a sex-ed lesson; this results in the kids (particularly Maya) talking about "penises" and "vaginas" and "thrusting" and asking questions about their parents' sex lives.
Violence
Some sharp words exchanged in a couple of scenes. Will breaks a bottle in anger.
Language
Pretty mild; infrequent use of words like "ass," "bitch," and "hell." "S--t" is used a handful of times in one scene.
Social
Behavior
Characters are all flawed but very human, with mostly good intentions. Will and Maya's mom clearly care for her very much and want to protect her from their problems. One character cheats on another; another kisses someone when he's dating someone else. Some pressure for a journalist character to compromise her ethics. Lots of discussion of politics and ideals, particularly concerning Bill Clinton's presidency.
Consumerism
Brief appearances by Corona beer, Pepsi, NYC hotels and other landmarks. Specific cigarette brands are mentioned, and there's a quick reference to Quaker Oats/Froot Loops, but the biggest "brand" is Bill Clinton and the Democratic party.
Drugs / Tobacco /
Alcohol
Adult characters drink beer, wine, and liquor, mostly in social settings. A few scenes in which Will is obviously drunk (motivated by frustration over where he's at in life). Will and April both smoke in the early-'90s scenes (though present-day Will has quit and tells Maya that he was stupid to have ever smoked); in one scene, they bet each other whose cigarette will burn faster -- the ensuing "race" makes smoking seem glamorous and almost romantic. Some minor smoking by other characters.