Gossip Girl’s Top 10 OMG Moments!

5. Three's a Crowd

Fearing they're missing out on the college experience, Olivia (Hilary Duff) hatches a plan with Dan (Penn Badgley) and Vanessa (Jessica Szohr) to have a threesome. One problem: after the deed is done, Dan develops feelings for Vanessa, creating a messy love triangle.

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