Ashton Kutcher (What Happens In Vegas) plays Reed, an overzealous florist who proposes to his girlfriend Morley (Jessica Alba) on Valentine's Day. It's his business, and his story, that forms the throughline for the other relationships in the film, each of which is lumbering towards its own mini- or mega-milestone: elementary-school teacher Julia (Jennifer Garner) discovers that the handsome doctor (Patrick Dempsey) she loves lives a second, secret life; after a night of passion, mailroom clerk Jason (Topher Grace) and personal assistant Liz (Anne Hathaway) struggle to tell each other how they feel; happily-married couple Edgar (Hector Elizondo) and Estelle (Shirley MacLaine) try to help their grandson Edison (Bryce Robinson) deliver flowers to a V-Day crush.
Meanwhile, Grace (Emma Roberts) begins to discover that you can't manufacture magic moments after she decides to give away her virginity to her boyfriend Alex (Carter Jenkins); Kara (Jessica Biel) struggles to juggle an overstuffed calendar, a disappointing love life and a holiday that she hates; and Holden (Bradley Cooper) and Kate (Julia Roberts) share a long flight home en route to see their loved ones, sharing their own romantic secrets along the way.
Suffice it to say there's probably at least one of these vignettes that will apply at least vaguely to your current relationship status. But Valentine's Day is essentially constructed on a foundation of three basic rules of its own: (1) people in the film behave according to the demands of the screenplay, not "realism" or even basic human nature; (2) they can't learn lessons until they've made every bad choice possible, and then offered someone else a solution to their own problem; and (3) with the exception of bad people who don't want relationships or screw them up, every problem of a person who wants to be in a committed, long-term relationship can be solved within the span of a single day.
In virtually every scenario, the real "problem" each relationship suffers from is people being unable to get over themselves, and probably more importantly, get out of their own way. But they also have to get out of the screenwriter's way as well, and it's that ham-fisted overabundance of manufactured "conflict" that keeps things not only from being less than tidy, but truly interesting. In one scene, a guy tries to tell his female (best) friend that she's running off for a rendezvous with a man she doesn't know is married, and she literally talks nonstop about herself rather than listening to him; I'll give you two guesses whether the two longtime pals end up together at the end of the film, but if they know each other so well and are so perfectly suited, why and how would she be so obnoxiously oblivious to something serious he had to say?
Otherwise, the rest of the hiccups in these relationships are verbalized rather than acted out, or even acted upon; with so many characters to explore in a two-hour span of time, it seems like director Marshall and screenwriter Katherine Fugate had to reduce each story to one happy scene, one conflict scene, and one reconciliation/ resolution scene, which left zero time for real characters, much less character development. For example, if you are a power-suited alpha female with no time for a relationship, then that's all you are. Not to mention that fact that it's not so easy to sympathize with a character's woes when she's played by someone like Jessica Biel; mortals have enough difficulty cultivating relationships amidst their personal obligations and professional duties without looking like, well, Jessica Biel, so her self-pity seems slightly disingenuous.
That's not to say that Biel is bad in the role, mind you, and in fact most of the actors serviceably fulfill the demands of their one-note characters. And quite frankly, I'm all for films that make you feel all warm and fuzzy and good and in love after you see them, even if the recognition you respond to is itself universal or generalized. But the sort of eclectic and inspiring anthology that Marshall is trying to make is something like (in fact, desperately like) 2003's Love Actually. The difference between the two, however, is that Curtis' 2003 tapestry somewhat approximates the complexities of actual love.
Valentine's Day, on the other hand, is as uncomplicated as a box of chocolates that all have the same gooey filling; worse yet, it feels like all empty calories and no satisfaction. In which case, stay home and rent Love Actually, or better yet, spend quality time with a loved one. I guarantee you'll learn more about relationships with a companion than you will by watching this movie, and best of all you'll have an enjoyable experience that doesn't require you to temper your enthusiasm before it even starts.