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18 TV Friends Who Dated the Same Person
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38

. . . and Dan Humphrey!

Dan (Penn Badgley) and Serena begin dating in Gossip Girl's pilot episode and continue on and off throughout the series, ultimately tying the knot. It is during one of their "off" phases that Dan and Blair become more than just friends, in season four. Oh, and Penn Badgley and Blake Lively also dated off screen for three years.

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