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.

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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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Copyright Disclaimer under section 107 of the Copyright Act 1976, allowance is made for “fair use” for purposes such as criticism, comment, news reporting, teaching, scholarship, education and research. Fair use is a use permitted by copyright statute that might otherwise be infringing. Educational use tips the balance in favor of fair use.

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💬 Comments on the video
Author

Only a female would wear something that leaves 70% of their boobs exposed and expect men not to glance at them. Geez

Author — OnePieceLover1175

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99 percent of men Will stare at that breast is it was this exposed, , The rest 1 percent are GAYS

Author — TheButcher DS

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So we're just going to ignore the fact that Jimmy Kimmel has a senior citizen as his Security guard?

Author — soulassassin0g

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2:57 Conan is just saying what everyone man is thinking. Why are you showing off your body THAT much, and then getting mad when guys look at you? Literally makes no sense.

Author — Miguel Claridy

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*Donald trump will kill both of us* . literally

Author — YouTube YouTube

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To be honest, if a woman has her chest out and exposed like that, guys tend to look. It’s the same when a guy is shirtless, girls will look.

Author — Sophie Louise

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She wears a dress like that and expects him not to look.

Author — Captain X-Raygaming

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that last chick with her legs and glitter dress was so sexy

Author — Ryan Zad

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Jail time and no job. If you dis this now.

Author — Edoty

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Andy Dick isn't flirting, he's being the comic character persona he's always played. And it's obviously a rehearsed bit.

Author — Trojan Lamb

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When Drew Barrymore flashed the incredibly older David Letterman I couldn’t help but think about how youth in Whorelywood are groomed for sex. She thought it was totally natural. So sad.

Author — SHOzFST

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I'm a woman and if find it HIGHLY hypocritical to ask a man not to look at your assets when you are doing everything you can to fully display them! Depending on where I'm going and who I might interact with, I do dress accordingly. Come on!!!!

Author — StoryeTime

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The Andy thing was actually real, not staged.

Author — TheSweetestJerk

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At least Conan was being honest and ya can't blame him. My guy😎

Author — Bruce O'Neal

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All of this is now considered sexual harassment

Author — Tibo Smolders

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So what's up with drew barrymores croch area? Is that a tear or just the style of the pants...?

Author — Sunny Raben

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I've never even heard of Ivanka until Trump became president.

Author — soulassassin0g

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what's the point of dressing skimpy when you don't want others to notice. I sense hypocrisy.

Author — Indra Joseph

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Conan handled it like a pro... putting her in her place like she deserved!

Author — Skerdy

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Omg ivanka is a divine goddess in human form

I would give her so many beautiful babies

Author — Dumbledores Auror