Chuck @ 8pm
Chuck's out of luck and pluck. Not only is his bizarro relationship with CIA ravisher Sarah still overly complicated, but Jill — his college sweetie and longtime love — turned out to be a spy. Chuck, still stung from that personal betrayal, keeps busy tonight, using spy work as a coping mechanism. Casey's also reeling (and we thought he lacked a heart) as he discovers his mentor (Carl Lumbly) has become a rogue agent. Meanwhile, Awesome's parents (Bruce Boxleitner, Morgan Fairchild) pay a visit. And we get more at Buy More: The efficiency expert (Tony Hale) works to reestablish the "employee of the month" contest.
Gossip Girl @ 8pm
Romance is in the air at the annual Snowflake Ball...but on Gossip Girl, romance is always complicated. Since Chuck and Blair are currently just friends, they try to find the ideal date for one another — and because they're Chuck and Blair, they make a bet out of it. Meanwhile, Aaron's ex-girlfriend is interested in Dan, and this bothers Aaron's present girlfriend (aka Dan's ex-girlfriend), Serena. Then there's Jenny, Nate and Vanessa, three points of a potentially messy love triangle.
Prison Break @ 9pm
This series is sort of like the myth of Sisyphus: push that rock up to the top of the hill and... you know what happens next. So now it's Self who has Scylla, and the full extent of his treachery becomes clears in tonight's bloody episode. In fact, if you can keep track of who's stabbing who in the back (and why), you just might be as smart as Michael. It also might be wise to keep in mind the No. 1 rule of diplomacy: Alliances shift but self-interest doesn't.
Boston Legal @ 10pm
Tonight's episode is on drugs. Now that doesn't mean this show's trademark frivolity is chemically induced. Rather, it's just that Denny's Alzheimer's prognosis gets a whole lot worse, and Alan appears before the Massachusetts Supreme Court to plead for his friend's access to an experimental medicine. In addition, Jerry and Katie help a girl whose acceptance to Harvard was rescinded after it's revealed she took nootropics, aka brain enhancers, for her SATs.