★ How I feel about this character: at the very beginning of the show, Dan was my favorite character. True story. I thought he was the only normal person among them all, and I found him cute most of the time. I liked him throughout the first season, and then he started to annoy me. I think he feels “morally superior” to the Upper East Siders, which may have been true at the beginning, but he also secretly, desperately wants to be part of them. He criticises and admires them at the same time, which didn’t really work for me after the first season. He blames them for the plots and schemes, but most of the times he ends up plotting and scheming with or against them. I think he’s a bit of a hypocrite. He blames Serena for all the lies and promiscuity, and then he goes off to entertain two girls at the same time, without them knowing it, lol. He actually thinks of selling Chuck’s story to the papers (twice) going against all his principles. He tricks Blair when she asks for help in winning Chuck back, because for some reason he doesn’t really think that someone like Blair could be in love. I didn’t even like how he was 100% convinced Blair got the internship at W just because she was Blair Waldorf. And I never really understood the way he and Nate have let Serena treat them. The way they ALWAYS go back to her, no matter how badly and carelessly she treats them with the whole “I don’t know who I’m gonna choose” thing. I just don’t have an opinion about him right now. I mostly don’t care about him. Granted that the writers never really gave him a decent storyline after the first season: it’s not like they did him any kind of favor…
★ All the people I ship romantically with this character: the only couple involving him that I’ve ever really shipped is Dan/Serena. I think they’re endgame, but I don’t know if I would enjoy them as a couple as much as I did back in the first season.
★ My non-romantic OTP for this character: as I said, I like his friendship with Blair. I think it’ll help them both to overcome all the prejudices they have about each other’s world. I used to like his interactions with Nate too, back in the second season.
★ My unpopular opinion about this character: I don’t know if it counts, but I don’t find Penn attractive at all.
★ One thing I wish would happen/had happened with this character in canon: I really like brother/sister dynamics, so I guess I would have liked to see more of him and Jenny together.
