David Letterman is no stranger to awkward interviews. The host has a history of scrapping content from the pre-interview and going off in his own direction.

We assume he pulled that stunt a couple of times alongside Jennifer Aniston. The two have a history of uncomfortable interviews, which featured Dave sucking on his guest's hair, and praising her "tremendous legs."

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Nonetheless, a lot of females in the past have fired back at the host, including the likes of Angelina Jolie. Jennifer Aniston is no different, as the guest always managed to diffuse bizarre situations with her charm and quick wit. This situation as we'll see was no different.

Jennifer Aniston And David Letterman Have A History Of Awkward Interviews

For those that watched David Letterman's 'Late-Show' religiously, there is no doubting that the host had a few awkward interviews with female celebs in the past.

He basically made Lindsay Lohan cry on national television, while he got uncomfortably close to the likes of Cher, Madonna, and Catherine Zena-Jones, just to name a few.

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Unfortunately, Jennifer Aniston can also be added to that last. Early on in her career when the 'Friends' fame started to hit, she appeared on the show and the interview was very hard to watch.

At the end of it, Dave awkwardly says, "Excuse me if this is rude I just want to try one thing." He would proceed to put Aniston's hair in his mouth and suck on it... She was a sport about the entire ordeal, though looking back, it was hard to watch.

Much to everyone's surprise, she would return to the show, despite the awkward incident. This time around, things really wouldn't change.

It was yet another awkward interview and in addition, Letterman wouldn't stop asking a certain question related to Jen's private life.

David Letterman Wouldn't Stop Asking Jennifer Aniston About Her Relationship With Vince Vaughn

Once again, the interview would get off to a very awkward start, with the host complimenting Jen on her look, "Wow, you look great. That's a tremendous outfit and the reason that's a tremendous outfit is because you have tremendous legs." Jen would try to downplay the situation by stating that it was hot out so she decided to wear shorts.

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Then came more awkward questioning, with Dave asking Aniston how her co-star Vince Vaughn was doing. That would be one of the many times Dave asked the question throughout the interview. He would later take things a step further, by asking the 'Friends' star if the two were dating.

Jen was obviously uncomfortable answering the question, so she tried to switch topics, however, Dave wouldn't give up, repeatedly asking what was going on between the two.

Jennifer kept things classy despite the repeated efforts to get it out of her. Even at the end of the interview, Letterman continued to poke away, stating, "Good luck with the film, and good luck with your non-going-relationship with Vince Vaughn. That's if you ever get together."

Jen looked on with nothing but a smile, handling the entire ordeal the best way possible.

Looking back, fans have nothing but praise for Aniston and the way she handled herself throughout the entire interview.

Fans Applauded Jennifer Aniston's Professionalism Throughout The Interview, Despite Letterman's Awkward Compliments & Questions

Over the years it became very apparent, Aniston became more of a Jimmy Kimmel kind of guest, as the two grew a close relationship with one another.

As for her time alongside David Letterman, fans had nothing but praise for the actress and the way she handled herself, despite the awkwardness.

"Damn, Jen handled this entire awkward interview with such poise and graciousness. Letterman was clearly making her feel terribly uncomfortable. As we know it's not like Dave necessarily respects his guest's pre-show agreements not to ask certain questions."

"The fact that she came back on this show."

"She is a beauty and a class act through and through. She never changes, she's always poised and graceful."

"Letterman's in on the joke, the studio audience is in on the joke, the home audience is in on the joke, and the guest is the joke." - Norm MacDonald"

Kudos to Jen and her appearances on the show, despite things going south at times, she always managed to pull it together.

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