9. The Sixteen Year Old Virgin
Season 3 Episode 15
Jenny almost loses her virginity to Damien. Even though she did something very, very smart by turning him away, she still lets everyone think that she did sleep with him.
When watching this episode sometimes it’s hard to believe that just the season before she was following her dream of becoming a fashion designer. And in this episode she’s the queen of Constants and going down a very bad path. She may have kept her virginity, but things still became dark for Jenny.
Dan and Vanessa were exploring becoming more than just friends. They think trying to make rules and boundaries is going to make it work. They soon find out it doesn’t. I’m a fan of Serena and Dan, but the Dan and Vanessa relationship had to be done eventually, just like the Nate and Serena relationship.
From the beginning Nate was in love with Serena. That had to lead them to each other at some point. Nate and Serena were very different from her other relationships. I think because they are such good friends. It was never meant to last.
With Jenny planning to lose her virginity that brought back up some old issues. Nate had lost his virginity to Serena and the very next morning she was gone. He felt very strongly to not let Jenny make a horrible mistake, even if he was going by it in a completely wrong way. All he was doing was driving her closer to Damien.
If the new relationships and Jenny’s impending sexual relations wasn’t enough drama for you, Chuck gets manipulated by his mother and uncle. I think manipulation and betrayal is just in Chucks blood. It’s amazing he’s turned out so well. There was a few dark detours on the way though.