Tragedy strikes the lives of the Upper East Side teens and their parents.
Blair and Chuck make a bet that they can find the perfect dates for each other for the annual Snowflake Ball; Aaron's ex-girlfriend expresses interest in Dan, creating conflicting feelings for Serena.
Uncle Jack Bass (Desmond Harrington) arrives in town to try and help Chuck pick up the pieces; Blair tries to get accepted into Colony Club, the most prestigious ladies club in the city; Jenny returns to Constance Billard.
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