Meanwhile, Dan has begun dating Serena van der Woodsen, a fact that Vanessa is hurt by when she finds out.
However, Blair feels that Vanessa is harboring feelings for Dan and warns her to back off his and Serena's relationship.
In Seder Anything, Dan and Vanessa play a game of Never Have I Ever.
She reveals that she slept with Chuck twice and that Rufus Humphrey confided in her that Dan was denied financial aid at Yale.
Meanwhile, the two become friends with celebrity student Olivia Burke.
Dan begins dating her and all is fine until the three engage in a threesome (They Shoot Humphreys, Don't They? Afterwards, Olivia is hurt, due to her seeing Dan and Vanessa ice her out during their threesome.
She tells the two that they seem to have feelings for each other and leaves school to shoot a movie.