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

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Shared April 13, 2017

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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talk show 2017 ahok

Justin Bohemier

Conan is a master at turning awkward moments into comedic gold

10 months ago | [YT] | 10,077

Amelie Pearce

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

4 months ago | [YT] | 2,105

jayden garcia

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

5 months ago | [YT] | 4,061

Harveen Banga

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

2 months ago | [YT] | 1,092

Manny Lugz

Everybody thought the Andy Dick episode was a joke but it turns out to be real. He really fondled Ivanka and he really got dragged out.

5 months ago | [YT] | 1,601

Kurt Riprock

I'm gonna design a pair of pants that shows 1/4 of my nut sack. Then when a woman looks at my balls I'll say, my eyes are up here.

3 months ago | [YT] | 1,091

Dark Knight

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.

2 days ago | [YT] | 4

Lol At life

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

2 weeks ago | [YT] | 157

Xiao Ran Li

Jimmy Kimmel handled that really well. He didnt care if he has to drag him in the middle of the interview, he was being inappropriate and he deserved it

4 months ago | [YT] | 691


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.

9 months ago | [YT] | 4,856


Has anyone seen Andy since Trump's election?

5 months ago | [YT] | 847

Kevin Lange

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

2 months ago | [YT] | 573


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

1 week ago | [YT] | 50

Tauqeer Ahmad

“Trump will kill.. both of us”😂😂

1 week ago | [YT] | 80


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

3 weeks ago | [YT] | 138


Holy shit they really dragged him out of there huh LMAO

3 months ago | [YT] | 371


Sarah shahi is fine af... what a milf... she's a goddess

1 month ago | [YT] | 135


jimmy kimmels security looking outdated.. crawling on the floor like " help ive fallen an i cant get up"

4 months ago | [YT] | 276

Cocaha 87

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

9 months ago | [YT] | 5,615


If you were able to cash in being famous, that's what Andy did. "That was brillant" Said Trump 1:26

3 weeks ago (edited) | [YT] | 4