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