Lisa (Reese Witherspoon) is a beautiful 31-year-old softball player on the U.S. Olympic team and softball is her life. She's the mentor for all the other girls on the team, but she's starting to show her age in a sport where your edge is everything and so she gets cut from the team. This causes her to realize that she just might want to think about a future with a husband and kids, but she's not quite ready for that. She's dating Matty (Owen Wilson), a charming professional baseball player and notorious ladies man, and while they are having fun, she's not so sure she sees a future with him. Enter George (Paul Rudd), a guy one of her teammates passed her phone number to in the hopes she might try dating a non-jock. George initially makes an idiot out of himself, but the pair eventually goes out on a date - on the worst day of both of their lives; the same day Lisa gets cut from the team and George gets investigated by the government for fiscal wrongdoing at his father's company. Even though the date is a bit of a disaster, George keeps Lisa on his mind, even as he goes through the investigation. Meanwhile, Lisa decides to go full-forward in dating Matty despite his personal shortcomings, like dating other girls.
George soon discovers that, although he was clueless about the goings-on at his work, his father, Charles (Jack Nicholson), seems to know more than he first appears. As George feels the walls closing in on him, a ray of sunshine peeks through when he bumps into Lisa in the elevator of his father's building. As it turns out, Matty lives in the building as well and Lisa has recently moved in with him. When she brings George over to the apartment to meet Matty and he goes a bit ballistic at Lisa having another man over at his apartment, she starts to see that maybe he isn't Mr. Right. She leaves Matty, turning to George to share an evening and discovers the world of trouble he's in. Just when she thinks her future is with Matty, she starts to have feelings for George. As the title suggests, all Lisa wants to know his How Do You Know when you are in love?
There is some comedy in this film, although it doesn't happen often enough for me to consider this a comedy. There is romance, but when you have Matty discussing how to determine if you are in love with his teammates, and the best explanation they can come up with is, "I wear a condom when I am with other girls," well, that's not super romantic. Kathryn Hahn plays Annie, George's steadfast and very pregnant assistant and she is a funny lady with really good comedic timing. In another scene where Charles is trying to explain the severity of the investigation to George, but George is trying to get to his first date with Lisa, Charles tells George that he can't run away from bad news and George literally does run away. That was really funny and was probably the best scene in the movie. But overall, it just seemed like a movie made up of filler. There were two storylines going on, one with Lisa and Matty and one with George and Charles, and while they eventually overlapped, they just didn't gel well.
As far as special features go, there are quite a few and most of them clock in at 30 minutes in length each, but again, they just didn't hold a lot of appeal for me. The Blooper Reel was pretty funny, but the Deleted Scenes (about 30 minutes worth) were best deleted. There's a conversation between James L. Brooks and Hans Zimmer about how they collaborated on the musical score, there's a making-of featurette, a commentary on key scenes with Brooks and Wilson (another 30 minutes of scenes) and filmmaker commentary on the feature film. Finally, there's an interactive script gallery where you can page through the entire script, plus a very brief featurette on how to make George's signature drink, which sounds delish.
As for the Blu-ray aspect, sure it looked crisp, but there weren't really any standout scenes that screamed for Blu-ray. Surround sound was there, but it just didn't make that big of a difference. If you are looking for a sort-of comedy with a sports theme, you may want to give this one a rent. As for fans of the typical Owen Wilson, Paul Rudd or Reese Witherspoon film, you may come away disappointed. I did.