(#14) He Dated Rachel’s Sister
Season 6, Episode 13, "The One With Rachel’s Sister"
Ross dates Rachel’s sister Jill, despite all the awkwardness. However, he wins a few bonus points for eventually calling the whole thing off.
(#17) He Flirted (VERY) Unsuccessfully
Season 5, Episode 10, "The One Where Ross Can’t Flirt"
Trying to prove that he can flirt, Ross makes several passes at the pizza delivery girl. Spoiler alert: he fails miserably. He ends up saying he likes eight-year-old boys and talking about the smell of gas. That’s no way to attract girls.
(#3) He Threw a Memorial Service for Himself
Season 9, Episode 17, "The One With The Memorial Service"
When Chandler posts that Ross is dead on their alumni website, Ross gets mad that no one cares about the news. So he proceeds to make Chandler throw a memorial service. Not only that, but when a cute girl shows up, he appears out of nowhere and completely freaks her out. "You sick freak! Who does that?!" she asks. Same.
(#2) He Lied to Rachel about Getting the Annulment
Season 6, Episodes 1 to 5
After they get drunk and married in Vegas, Rachel and Ross decide to get an annulment. He promises to take care of everything, but changes his mind because he doesn’t want to have three failed marriages. Of course, he also lies to Rachel about the whole matter until it's too late and they have to get a divorce. Could he be any creepier?
(#5) He Pretended to Be a Masseur Because Some Girl Was Hot
Season 7, Episode 2, "The One With Rachel’s Book"
When one of Phoebe’s massage client’s shows up unexpectedly at his door, Ross lies about being a masseur, thinking she’s the one in need of some rubbing. Joke’s on him, because the appointment was for her dad. Silly Ross.
(#11) He Cheated on Rachel
Season 3, Episode 15, "The One Where Ross and Rachel Take a Break"
Break or no break, you don’t sleep with another woman four hours after a huge fight with your girlfriend. Not only did Ross cheat on Rachel, he also spent half of the next episode running around to make sure she would never find out. Not cool.
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"Friends" is considered one of the most popular and influential sitcoms in TV history. Even if this TV series ended a long time ago. Each character on the TV series has a unique personality and humor. Among them, Ross always makes the audience laugh because of his stubborn and goofy but lovable demeanor. He always talks about profound scientific principles, which makes others drowsy.
It is surprising that in the "Friends" special prepared by HBO, the 6 main leading characters will return, which makes many fans look forward to it very much. Here the random tool introduced 17 creepy things Ross ever did that every loyal fan knows.
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