Career Resurrection: After falling out of the Hollywood limelight in the early-2000s, Matthew Lillard's well-received role as the man Elizabeth was cheating with got him back on the radar and lined him up with several other dramatic live-action roles, including a stint on FX's The Bridge (US) and playing antagonist to Clint Eastwood in Trouble With The Curve
Dawson Casting: Shailene Woodley was twenty-one playing the seventeen-year-old Alex. Nick Krause was nineteen as Sid, who is implied to be the same age as Alex.
George Clooney garnered arguably the most praise of his career for playing a character who is neither the slyest or most intelligent man in the room, but just a stressed-out father dealing with his dying wife and estranged children. Clooney took the part precisely for this reason.
Amanda Seyfried auditioned for Alex, but was turned down for being considered too old to play a seventeen-year-old. Kristen Stewart and Brie Larson also auditioned for the same role.
The script was generally more explicit about Sid being Alex's boyfriend, with Matt telling them not to do "anything" under his roof to which Sid replies that he can't really stop them and later talk about them theoretically getting married in the future (though they both say they aren't going to get married). In the movie, there's nothing that particularly implies they are more than just friends (though you could still assume they are dating with how much time they are together).
