When they were 16, Dan told Vanessa he loved her as more than a friend but she rejected him, as her family was moving to Vermont.She returns during the first season and while the two remain just friends for awhile, they eventually begin dating.Together they create a video projector display of snow, since Dan wants snow for Christmas.However, Blair feels that Vanessa is harboring feelings for Dan and warns her to back off his and Serena's relationship.After briefly serving as frontman for the band The Raves, he hooks up with one of the instrumentalist's wives and later experiments with being gay.He eventually attends Evergreen State College but realizes he truly loves Vanessa.She subsequently ends their relationship and begins dating Blair Waldorf's stepbrother, Aaron Rose.He and Vanessa reunite after he sends her a toy from Japan to film.
In Chuck In Real Life, Blair and Chuck Bass team up to humiliate Dan and Vanessa by having Chuck seduce Vanessa.
At Christmas, Vanessa reveals to Dan that her present is that she had a story of his, titled , sent to The New Yorker and will be published that summer.
After unsuccessfully searching for the perfect present, Serena asks Vanessa for help in finding one.
Afterwards, she moves to Spain and passes the royalty check on to Dan.
After being friends for years, Dan realizes he has feelings for Vanessa and the two enter into a relationship.
She's especially hurt when Dan ignores her to help Blair carry out a scheme to help Serena.