Award Snub: Neither Portman nor Owen winning the Best Supporting Oscar in their respective categories. A bit of a surprise, given that they each nailed the Golden Globe and the Globes tend to be a preview of the Academy Awards.
The cybersex scene between Dan and an unwitting Larry.
To say nothing of Larry and Anna's subsequent awkward meeting in the aquarium the next day. Anna realises he's been pranked and finds it Actually Pretty Funny, while Larry is at first in complete denial that he wasn't really talking to a woman.
Magnificent Bastard: Larry. Essentially engineers his and Anna's reconciliation, as well as Alice and Dan breaking up for good by blackmailing Anna into sex — he bluntly admits that he did this for the sole purpose of fucking with Dan — and later telling Dan that he slept with Alice as well. Sure enough, Dan reacts exactly as Larry predicted — he can't deal with either revelation and his relationships with both women end. Larry gets his wife back, Alice moves on with her life, and Dan is left alone and dejected.
She Really Can Act: An odd example. Julia Roberts was considered the weakest of the four leads in anticipation of the film. Although she had an Oscar win for Erin Brockovich, she was heavily typecast as The Ingenue in romantic comedies. Here she's slightly against type - Jane for instance would be the role more within type for her - and she was given lots of praise. Anna is considered one of her more underrated roles.
Strangled by the Red String: The film does this with the pairings, thanks to multiple time skips that don't fill in the blanks. Dan decides he's in love with Anna after one kiss. Anna gives Dan the brush-off. . .but the next scene has them confessing to their respective partners that they've been having an affair for over a year. Anna reassures Dan of her love for him despite having slept with Larry. . .the next scene reveals that she went back to Larry. Alice rebuffs Larry. . .but Larry is later seen taunting Dan about having slept with her. Dan is depressed over Anna leaving him. . .the next scene is of him and Alice in bed, having reconciled and all we get to explain this is a brief flashback of him tracking her down at the strip club. It gets jarring.
Tearjerker: The fights between the respective couples regarding their infidelity are brutally realistic and quite uncomfortable for anyone who's been in the same situation.
Tear Jerker: Pretty much the entire album, but especially the last four songs, which are some of the bleakest musical recordings in history. More than one person has described the lyrics on the album as "suicide notes set to music."