Penn is ranked #35 in AIM's "100 Celebs Under 25".
In the US Elections 2008, Penn campaigned for Senator Barack Obama.
As of 2008, Penn resides in New York.
In his spare time, he enjoys playing soccer and writing music.
Penn claims to be very close to his parents.
Penn's first kiss was when he was only 11 years old.
Penn's dream job, besides acting, would to be a paid musician.
Penn's TV guilty pleasure is Friends reruns.
Penn got his name when his dad was bouncing a Pilot Penn tennis ball in frustration while trying to come up with baby names. When his mom got her ultrasound he referred to the baby looking like the size of the tennis ball. So they named him Penn.
Penn was nominated for a Teen Choice Award in 2008, for Choice TV Actor: Drama for Gossip Girl.
Penn is a 2008 member of the American Red Cross National Celebrity Cabinet. Members of the cabinet help out using their talents and resources in furthering the cause of the organization.
Penn and the rest of the Gossip Girl young cast were featured in People magazine's World's Most Beautiful People of 2008.
Penn's mother once drove him 50 miles to appear in a community production of Music Man.
One of Penn's favorite bands is Incubus.
Penn admits that among all the actors of Gossip Girl, he's the one who adlibs the most due to the awkward nature of his character.
Penn has been living in Manhattan since the start of the filming of his CW show Gossip Girl.
Penn turned down the role of Dan Humphrey twice before accepting.
Penn was chosen as one of People Magazine's Sexiest Men Alive for 2007.
He has an older half sister.
Penn's most embarrassing moment was forgetting the words to "The Star-Spangled Banner" while singing at a minor-league baseball game.
Penn is 5' 10½" (1.79 m) tall. He has black hair and is left-handed.
In 2001, Penn was nominated for a Young Artist Award for his performance in the TV series The Young and the Restless.
Penn owns an Audi.
Penn did some voice acting in some of the Mario games like Mario Tennis in 2000 and Mario Golf 64 in 1999.
Penn has appeared in the following videos as himself: Kodiak Yearbook and Grrrl Power.
Penn got his GED at the age of 13, so he and his mom could move to LA, so he could start auditioning.
Penn: (On playing the outsider in Gossip Girl) What's great about Dan, on one hand, is that he's the most relatable, because he's the "everyguy." But he's also sort of on a moral high ground, which, not that it can get boring but it's more fun to explore the darker side of a character. I really like the scenes where I'm able to work with his temper a little bit and do something a little more exciting.
Penn: (Advice he wished he was given growing up) I wish I had known that vulnerability is universal for everyone, regardless of how cool or not cool they are. You have such a heightened awareness of yourself, so even small things seem life-changing- a bad day turns into, Oh my gosh, my life is over. If I were still a teen, I would want to hear: "It's okay. Take a deep breath and move on."
Penn: One thing is that music is really my number one creative passion. I play piano and guitar, and I write music as well. But I'd never do it professionally. Maybe later in my life, I'll have the money to make an album on my own and do whatever I want, but until then I'll just keep it for me. I did once write a song for a girl. I think it was a really romantic gesture- and I think it worked!
Penn: When you're wet and your clothes cling to you, you feel more exposed, almost more naked than naked. Everything is more romantic by water. Everyone remembers his or her first kiss in the pool, in the rain.
Penn: (on his male fans) A lot of times [a male fan] will come up, you know, and it will just be a guy. And he'll be like, 'Yeah, dude, my wife loves the show. She'd be so excited if she knew I met you.' And it's always like, through his wife. And then a lot of times, as the night goes on, he'll have a couple more drinks in him, he'll be like, 'Dude, you know what? I love the show too! I really do! I love it so much! Dude, I cannot believe…' and he will go on and on about the story lines...
Penn: (on being a celebrity) I want to do film. I want to be an actor- I don't want to be a celebrity. They are two different things, and people have forgotten that they are different. Because if you are one, you can be generally the other. Like if you are a celebrity, then anyone will let you be in a film or on a TV show, and if you're an actor, chances are if you are successful, you are becoming a celebrity.
Penn: (on acting in New York City) It's incredible to be young and live here and not have to clean up your dorm room.
Penn: (on getting recognized) Actually, multiple times a day. If I go out in the city, chances are it's going to happen, especially if Blake [Lively] and I are together. We have this Serena and Dan complex going, so people freak out if they see the two of us.
Penn: (on getting along with his "Gossip Girl" castmates) We actually get along incredibly well. We're all great friends. I was actually just texting Blake. We're really close. In fact, one of the things I'm most thankful for in this show, the whole experience has been the friendships. That's no shit. That's no lie. (Laughs)
Penn: (on relating to his "Gossip Girl" character Dan) I think everybody relates to Dan. He's the most easily relatable because he's the most real. He's the most vulnerable... He lives the most normal life. He's the most regular.
Penn: (on his "Gossip Girl" character Dan being compared to Adam Brody's character Seth of "The OC") People are probably going to see the similarities at any chance they can and be like "oh, he's just trying to be Adam Brody." I've already gotten that in a lot of the reviews, but I think if you pay a little more attention, I'm actually doing something very different.
Penn: (on the popularity of "Gossip Girl") I'll get mobbed by literally 40 school girls. It's like being a full fledged star, and that's surreal.
Penn: (on studying acting) I imagine I'll study at some point with somebody, as a craft, I'm still grappling with it. It's constantly evolving.
Penn: (on making his "Gossip Girl" character Dan gay) I don't think network TV really has the balls to make one of their [teenage] series' regulars gay. Let's say the show builds up to become a big hit, then I think they'd maybe explore it in year three or four. It would be an interesting thing to do. It could bring in a whole different demographic.
Penn: I'm a pretty determined guy. Once I set my mind on something, I make it happen.
Penn: Whether or not I'm successful, I want to do this for the rest of my life.