When a man (Jason Biggs) can no longer bare being the "friend" to the woman (Kate Hudson) he loves, he resorts to the extreme measure of hiring his friend (Dane Cook) to take her out and pretend to be the most uncouth cad, thus causing her to realize how lucky she is to have him. Or so he thinks. Also with Alec Baldwin, Lizzy Caplan, Riki Lindhome, Diora Baird and Taran Killam. Directed by Howard Deutch. [1:43]

SEX/NUDITY 8 - A man is on top of a woman, just as they are finishing having sex (we see a brief thrust and hear a moan); he rolls over and his bare chest is visible. A man kisses a woman, pushes things on a desk onto the floor, puts her on the desk, she lifts her skirt and he climbs on top of her and they kiss (it is implied that they have sex); we see them lying in bed together later.
► A man and a woman argue, she puts his hand on her clothed buttock, he puts her hand on his clothed genitals and they kiss (it is implied that they have sex). A man and a woman lie in bed together (it is implied that they have had sex), he is bare-chested, she gets out of bed and begins dressing, and then climbs under the covers and they kiss.
► A man and a woman watch exotic dancers wearing thongs (revealing bare buttocks) and bra tops: one dances in front of them and removes her bra revealing bare breasts, and another dances in front of a man, bends over and shakes her hips, he puts his head toward her buttocks and says he's looking in, and the dancer dances on his lap and her bare breasts are visible.
► A clothed man and woman sit on his bed, she empties her purse, which contains many sex aids in a variety of shapes and colors, he empties a box of pornographic movies on the bed, they kiss passionately and lie back on the bed (it is implied that they have sex). A man carries a crate filled with pornographic movies and we see one titled "Lawrence of Alabia" with a picture of a woman in a skimpy outfit (bare legs and back). A woman has a box filled with "masturbatory aids" (we see a few that are penis shaped and are of unusual colors).
► A man drops his pants (we see his bare buttocks and thighs from behind) and tells a woman (she's his girlfriend's mother) to perform oral sex on him; she runs away screaming.
► A woman wears a strapless bra and a very short skirt that reveal cleavage, bare abdomen and back. Women wear low-cut dresses and tops that reveal cleavage. A man answers his front door bare-chested and his pants hang low at the hip. A woman breast-feeds an infant (we see the top part of her bare breast). A man watches a pornographic movie and we see a woman wearing revealing shorts (part of buttocks are visible) and using a step machine.
► A man goes into a public restroom, where men are using the urinals, he squeezes their clothed buttocks, and then peers over the divider at one man and makes a crude, sexually suggestive remark. A man caresses a woman's clothed buttock.
► A man tells his son to kiss another man and to "stick your tongue in his mouth" (he does not). A man makes a sexually suggestive remark to his girlfriend's mother. A man talks to young boys (7-8 year old) about having sex, using descriptive terms. A man makes a joke about a priest sexually abusing a boy. A man describes, using crude terms, having sex with a woman and he includes sexual gestures (he's talks to his son). A man talks about having sex with his wife's sister (he's talks to his son). A telephone conversation between a man and a woman includes misunderstood remarks that can be interpreted as sexual. A man makes a crude remark to a woman about having "what he's having," referring to a nursing infant. A woman yells at a man saying, "we haven't even had sex yet." A man talks to another man about masturbating all the time. Several women in a bar admire a man as he walks passed them. A man licks a burrito in a sexually suggestive manner and a woman watches with an appalled look on her face. A man admires a woman as she walks passed him and makes a comment about "the new girl." A man asks if he can buy a woman a drink, she accepts. A man makes a crude remark about someone eating jam off a part of his boss' body. A woman tries to convince another woman to have casual sex with several men in order to get some experience. A man wears a T-shirt with a crude, sexually suggestive phrase on it. A woman talks about listening to the voice that comes from your genitals, using crude terms. A woman talks about the size of a man's endowment. A man talks about his infidelities. A woman confesses to being a serial monogamist.
► A man and a woman kiss outside a bar; another man leaves the bar with a woman who is not his fiancée. A man and a woman kiss in a few scenes. A man and a woman dance together and kiss.

VIOLENCE/GORE 4 - A man punches another man in the face (we see the man with a bruised face.
► Two men force a man out of a building. A man helping to carry a chair where a woman is sitting lets his side go and the woman falls to the floor (we hear a crash and there's some commotion). A man in an office screams and throws things off a desk, and several co-workers see this and are concerned.
► A man tries to convince a woman to have sex with him, he kisses her on the neck and makes crude remarks, and she slams a door in his face.
► A woman yells at a man over the telephone. A man and a woman argue and insult each other in several scenes. A woman accuses a man of making her pregnant, as well as her sister. A woman talks about having to put her dog to sleep after it bit her sister. A man talks about public defecation.
► A man trips and falls while jogging (we see that he has a bloody knee afterward). A hair stylist accidentally shaves a man's eyebrow off, and he then shaves the other off too.
► A woman vomits in a bathroom twice (we see goo and hear gagging), and a man vomits on a dance floor a few times (we see goo and hear gagging). A man urinates on a houseplant (we see the stream), and a man urinates in a cup in a car (we see him hold the cup below his waist). A man sneezes on a food buffet and touches the food with his fingers.

LANGUAGE 9 - About 45 F-words and its derivatives, 1 obscene hand gesture, 35 sexual references, 22 scatological terms, 72 anatomical terms, 11 mild obscenities, name-calling (creepy, old man, weirdo, nerd, fat, dork, anti-cupid, selfish, Satan, fraud, crazy, manic), 3 religious profanities, 10 religious exclamations.

SUBSTANCE USE - Two men smoke marijuana in a restaurant kitchen. A man drinks a lot of alcohol at a wedding reception and is very drunk, a man drinks alcohol at a bar, people drink alcohol in a bar, people drink in several bar and restaurant scenes, people drink wine at a restaurant, men drink beer and a man drinks alcohol in a bar scene, two women drink a lot of alcohol and they appear to be drunk. A man smokes cigarettes in many scenes throughout the movie, a woman smokes a cigarette, and a man smokes a cigarette in a church.

DISCUSSION TOPICS - Infidelity, romance, trust, relationships, pornography, love, find the person who is right for you, guilt, betrayal, forgiveness, emotional terrorism, humiliation.

MESSAGE - Even the romantically challenged can fall in love.

(Note: A restaurant is called "Chesus Crust" and the tag line is "Where pizza is a religious experience"; there are paintings on the wall of the Last Supper with the participants holding pizzas and the pizzas served in the restaurant are shaped like crosses. A woman who is religious is offended by this and calls all the people in the restaurant sinners, and a server says that if they hadn't stopped her mom outside the family planning clinic they wouldn't have to be dealing with her.)