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

Has anyone actually watched a late night show on tv or does everyone just see them randomly pop up in their recommended

Author — Cory


I’m a straight girl and even I find it hard not to look at Nicole’s cleavage

Author — Bella Holland


That poor security guard that fell and didn’t get helped up, let’s take a minute to appreciate him. 😂

Author — Amelie Pearce


Even if I dont like her, im sorry that was out of line and just disgusting of Andy to do that to Ivanka.

Author — Harveen Banga


everyone is saying that jimmy handled it well but man ivanka handled it amazingly

Author — jayden garcia


Wow, they could get away with a lot more in the 90s

Author — Michel Schweinsberg


And that’s when they hired Guillermo...

Author — Outtathewoods1


There’s regular talk show flirting, and then there’s Craig Ferguson show flirting. League of his own

Author — Kevin Lange


“Maybe you could teach me...”

“No, no I couldn’t...”

*Puts leg on table*

“Maybe I Could....”

Author — Ethan Davis


“Eyes up here Conan”

*proceeds to move her hair to show MORE of her cleavage

Author — Irsyadcoolboy


I'm glad they removed Andy, that was getting really disgusting now, beyond creepy

Author — Kgomotso Moyo


People watched Kimmel pulling Andy out of the show as a comedy improvisation while actually Kimmel was very pissed at him and deliberately kicked him out of the show.

Author — Fajar Setiawan


That Andy is a seriously disgusting person

Given his disgusting record, according to Wikipedia, why was he invited to ANY show after that at all??

Author — MorTobXD


Borat is an actor and was acting. But some of these are actually real and are kinda creepy.

Author — dixieandleona


Andy Richter "Hey Nicole, ignore the flowers" he's a comedy legend and deserves more credit.

Author — Doctor Strange


Aye that Jimmy Kimmel security guy dropped like a fallen angel lmao



12:58 when Sarah asks for the banana and starts banging it against the desk im like wtf is going through her mind.

Author — Knight of YouTube


1. Wtf Andy
2. You can't blame Conan at all.

Author — daAmazin FatB0y


Craig Ferguson did nothing, she was being free and sexually liberated but he did nothing and she was dropping hints everywhere. If the sexes were reversed everyone would lose their minds.

Author — Dark Knight


Holy shit they really dragged him out of there huh LMAO

Author — Brooke