Lonely Boy was our way into the impenetrable Upper East Side world. Slowly but surely he was shown the ropes, and we learned the tricks of the trade right along with him. Dan Humphrey’s comedic relief and outsider status made him our perfect gateway into ‘Gossip Girl’ binge-watching. Yes, he dated every female who ever was featured on the show. And yes, he turned out to be GG herself. But we also can’t forget his classier — and, more importantly, sassier — moments. Love him or hate him, at the very least we hope you enjoy this list for Penn Badgley’s array of hairstyles throughout the show.
Why We Love Him:
1. His self-awareness was gold.
2. Even when he was in his most annoying state, he still provided comedic relief.
3. He was the best at being awkward.
4. He loved Serena from the very beginning (cue the “aww”s).
Why We Hate Him:
1. Oh, youre an outsider? We had no idea. Please tell us more.
2. He acted like he was picky even though he dated every female ever to grace the ‘Gossip Girl’ screen.
3. We were supposed to find this attractive.
4. The horrible inconsistencies that were revealed when he became GG drove us insane.
5. He actually dubbed himself “Lonely Boy.”
But, at the end of the day, if Lonely Boy had never existed, we wouldn’t have this gif: