Extremely Awkward & Out of Control Flirting on Late Night Talk Shows

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Extremely Awkward & Out of Control Flirting on Late Night Talk Shows 4.5
A compilation of the most awkward, funny and downright shameless flirting on late night talk shows.

Andy Dick and Ivanka Trump:
Apparently, when there’s a Dick in the room pretty young girls are at risk. Or maybe he was just taking Donald Trump’s advice on wooing women when during an appearance on Jimmy Kimmel show, Andy Dick took to grabbing Ivanka by the leg. Things got so bad that the security had to physically remove Dick for the remainder of the show.

Nicole Scherzinger and Conan O’ Brien:
Sometimes staring at a woman’s chest is as involuntary as a knee jerk, especially if she’s wearing a clingy, low cut leopard print dress and her name is Nicole Scherzinger. According to science of course.

Dolly Parton and Jay Leno:
On flirting, Dolly Parton once said in an interview, “I love to flirt, and I've never met a man I didn't like. Men are my weakness.” Judging by this interview, her “healthy” upper body is Leno’s weakness.

Drew Barrymore and David Letterman:
In probably the most famous striptease in late night history, 20 year old Drew Barrymore impulsively performed sensual dance moves on David Letterman’s desk for his birthday. After flashing him and kissing his cheek, he gleefully responded, "You know, I can't thank you enough for that."

Martha Stewart and Borat (Sasha Baron Cohen):
Clearly didn’t know what she was getting herself into when she decided to show Borat how to make a bed, because all he had in mind was some sexy position playtime with naughty, naughty Martha.

Craig Ferguson and Sarah Shahi:
Craig Ferguson may reign supreme as the master of late night flirting however, he met his match in the very tipsy Sarah Shahi who admitted to doing a little drinking backstage.


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💬 Comments on the video

"i was hoping you could teach me"
"No i cant..."
*Puts leg on desk*
"Maybe i could"

Author — Jakor


Conan is a master at turning awkward moments into comedic gold

Author — Justin Bohemier


Jimmy Kimmel handled that Andy situation very well, he knew it genuinely wasn't right but removed him with humor to not make everyone feel uncomfortable.

Author — lucifer


It's not fair to Conan because he has eyes of steel and Nicole's cleavage is a magnet

Author — Cocaha 87


Andy is that guy u bring to the bar and he starts a fight every time

Author — Silky Slim


I sincerely hope Craig smashed that last girl after the show

Author — Terence Hardy


where's the "why did YouTube recommend me this?" squad at?😂

Author — bipul kharel


Kimmel may have been smiling but he wasn't kidding either; Andy Dick was sabotaging his interview, stealing laughs and or control of their conversation/interview. I don't think it was planned because Kimmel took the initiative in removing Andy out the door.

Author — swmita



Author — ZACK zack


A lot of people think the Andy Dick thing was a skit. So strange.
Obviously it’s real.!
Disturbing to look at.

Author — Cinsicko


Never heard of Sarah Shahi but I may need to research her now...

Author — Cyaneyed77


No-one stands a chance when Craig Ferguson walks into the room.

Author — Michael Eade


Conan’s physical comedy, He can be in movies. Reminded me of Jim Carey. So funny.

Author — Silver Girl


Is it a game to women to wear something that shows cleavage and then confront somebody when they quickly glance lol

Author — Audie EC


Borat really took off his underwear on tv what a legend

Author — M


"Stop Andy, Donald Trump will kill both of us " Epic .😀

Author — Jafar Salim


So much respect to jimmy. Andy was so out of line.

Author — Chelsea De La Garza


Oh look Kimmal actually passed for a decent human being then.

Author — James Matthews


Gordon Ramsey and Sophia Vergara is the U missed it. But good vid

Author — Number One


Sara Shahi is actually not that shahi after all...

Author — Surigen 12