The hilarious mishaps happened on his first and last day of filming the famous sitcom.
Paul Rudd is a pro at using his sense of humor for gain as he is the go-to guy for comedic relief in film and TV.
But the actor revealed he wasn't at the top of his game during the taping of the final episode of "Friends".
During an interview on Friday's "The Graham Norton Show", the 50-year-old recalled feeling out of place at the wrap of the sitcom juggernaut and his insecurities got the best of him -- and perhaps the worst of co-star Jennifer Aniston.
"The show was a phenomenon and I was in the very last episode, which made no sense to me whatsoever. I was on the sound stage and Jennifer Aniston was crying and I thought, 'I'm not supposed to be here,'" he explained. "So, to break the ice, I went over and said, 'Well, we did it! What a ride!' The joke inevitably fell flat."
It appears the actor likes to book-end life experiences because he shared another cringeworthy moment with Aniston on his first day filming the NBC comedy.
"I was on the set for my first episode and Jennifer was on a Segway because she had broken her toe, and everyone was marveling at it," he began. "Matt LeBlanc asked to have a go and immediately knew how to do it. I then asked to try it, too."
But, once again, things didn't turn out as planned for Rudd.
"I spun round and rolled it right over Jennifer's foot! The producers look of panic was if to say, 'Is it too late to fire him? Has his character been established yet?' I felt awful," he said. "Such an inauspicious start."
But the damage must not have been irreparable as Rudd and Aniston would go on to star as a couple in the 2012 film "Wanderlust".
Rudd played Mike Hannigan in the final two season of "Friends". Mike married Phoebe (Lisa Kudrow) in Season 10.
"It was an incredible thing to be part of and the whole experience, but seems a bit surreal and a bit of a blur in my memory,” Rudd said of his time on the show.