Anyone who's been in a long-term relationship knows it isn't always easy. But no one makes romance look more painfully complicated than Will Hayes (Ryan Reynolds). Whether he's simply unlucky or certifiably challenged, this boyishly handsome New Yorker appears destined for life in the single lane. And after spending nearly two hours watching his on-again, off-again love life, audiences will be equally convinced of his dismal chance for success.
Since leaving his native Wisconsin and his high school sweetheart (Elizabeth Banks) to pursue a career in the pre-election campaign office of Bill Clinton, Will manages to pull off a spectacular fundraising event, start a consulting company with another intern (Derek Luke) and father a child. Yet the political wanna-be can't maintain a healthy connection with a woman for any substantial time.
Now on the eve of his divorce, his daughter Maya (Abigail Breslin) wants to hear the story of how he met her mom. Despite his initial apprehensions, Will finally agrees to fill her in on his former life. Sparing no details, but changing the names to add to the mystery, Will divulges the nitty-gritty facts about his past habits of smoking, frequent drinking and casual sexual encounters with numerous women. He also informs his daughter of her mother's premarital activities.
Using a clipboard to keep notes, Maya tries to decide if her mom is the high school sweetheart who got left behind, the tough-minded journalist (Rachel Weisz) who cozied up with Will after being dumped by her grizzled thesis advisor (Kevin Kline) or the young Bohemian copy girl (Isla Fisher) from the campaign office.
Grilling her dad for all kinds of information, Maya, who has just had a sex education lesson at school, repeatedly uses anatomically correct terms during their discussions about how babies are made. But her graphic descriptions of the process aren't the only conversations that may leave real parents feeling uncomfortable in front of their children. Will's disclosures about experimental same sex relations, threesome activities and a professor who preys on undergrads seem like too much information even for the precocious preteen therapist who is more worried about her dad's happiness than her parents impending break-up.
Wrapped up like a big, heart-shaped box of chocolates, this film has all the ingredients you'd expect in a Valentines Day release -- gorgeous girls, serendipitous situations and a lovelorn hero in need of affection. But after watching these characters try to justify their half-hearted attempts at commitment and the pursuit of their own self-interests, this script definitely tastes more like the cheap, waxy knockoffs instead of a real chocolatier's confection.