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When Dan tells Vanessa he knows she's been offered this position, she insists on not going and staying in the city with Dan to work on their relationship.

Despite their competition, Vanessa is chosen by the program and although this causes further issues between the two, Dan eventually expresses pride in Vanessa.

Later, however, their relationship hits another obstacle when Dan discovers that Vanessa has received an offer difficult to reject: to work in Haiti, assisting the disaster aid as well as filming for CNN.

She simply states that his annual christmas CD mix is more than enough. Vanessa spends a lot of time with the Humphrey family, sharing a close bond with all of them since they've all known her for such a long time. When Dan becomes friends with Nate, and Nate starts dating Vanessa they all become close.

Vanessa also helps out Rufus Humphrey out a lot too, and in some of the episodes has a rivalry like relationship with Jenny since both of them have feelings for Nate.

=== Season 1 === Vanessa moves back to Brooklyn when Dan and Serena are still trying to figure out their feelings for each other.

It became apparent that Vanessa and Dan have history, and they dated in the past.

After Serena gets in a car accident, Dan and Vanessa are at the hospital, and Dan tells Vanessa that he loves her.

In Roman Holiday, Vanessa announces to Dan that she entered his short story in a competition, and he is now going to get his story published in The New Yorker.

At a cafe, Dan expresses his gratitude towards Vanessa and asks what she would like in return.

In Season 3, Dan dates Olivia Burke, and Vanessa dates Paul.

While Dan and Vanessa are showing Olivia the "ultimate college experience", the three of them have a menage-a-trois that leads to Olivia seeing that Dan has feelings for Vanessa, so Dan and Olivia break up.

Vanessa seems to want Dan back, but they don't because he's dating Serena.

Vanessa doesn't take it badly, after that Vanessa and Dan rekindle their old friendship and become friends again.

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