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18 TV Friends Who Dated the Same Person
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. . . Nate Archibald!

Nate (Chace Crawford) and Vanessa (Jessica Szohr) date briefly, off and on, during the first two seasons of Gossip Girl. During season two, Nate begins dating Jenny (Taylor Momsen), who keeps their romance a secret so that Vanessa — who is like a sister to her — doesn't find out. Spoiler alert: Vanessa finds out.

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