In this photo from the second-season episode of Gossip Girl, "The Ex-Files," Dan and Jenny share a conversation in their school attire. We like this brother-sister combo.
In the Season Two Gossip Girl episode entitled "The Dark Night," Dan and Serena look happy. But we know it's only a matter of time until something - big or small - conspires to drive them apart.
The funeral that's coming up on a future episode of Gossip Girl is a major event, and emotions are running high between Dan and Chuck in this photo taken on the set in November 2008.