Celebrities Who Have Dated Their Bosses

Gallery: Chelsea Handler And 9 Other Celebrities Who Have Dated Their Bosses

Posted by: Nikki Dowling Filed in: celebs, galleries
4:30PM, Wednesday August 26th 2009

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Chelsea Handler and Ted Harbert

“Chelsea Lately” host Chelsea Handler just broke it off with her longterm boyfriend, Ted Harbert. The thing is, this dude is also the CEO of Comcast, which makes him Chelsea’s direct supervisor. Which, uh, if there are hard feelings, could be pretty disastrous for Chelsea and fans like us who think she has the best late-night show out there. [NY Daily News]

Dating your boss is a tricky proposition. It can totally put your career on the fast track, but if the relationship ends, well, you could be out the door. Take a look at our slideshow of celebs who’ve dated their bosses to see the various scenarios of what can happen.

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comments

acannon
wrote on August 26 2009 @ 03:44 pm: [report]

Chelsea Handler is brilliant and hilarious! She deserved the Late Show spot on NBC instead of awkward side-kick type Jimmy Fallon

Pinky
wrote on August 26 2009 @ 03:49 pm: [report]

And here I thought Chewy was Chelsea’s squeeze ! I’m shocked.

julseymp
wrote on August 26 2009 @ 08:30 pm: [report]

Is it frustrating to anyone else that in all but one of these scenarios, the bosses are all men? Even though it is clearly a reality and a trend that female celebrities have dated/date their male bosses, there must be some other examples out there where the woman is the boss. I just feel like maybe these examples are perpetuating myths regarding the power dynamic between women and men.

Shriekback68
wrote on August 26 2009 @ 10:28 pm: [report]

It’s a power/wealth thing, julseymp. Men hold most of the power and wealth (still!) in this country, so it makes sense that the female celebrity/male CEO pairing is more common than the female CEO/male celebrity pairing. Although I’m a bit taken aback that Chelsea glommed onto a dumpy rich dude…she seems more substantiative than that. Oh well.

julseymp
wrote on August 27 2009 @ 07:26 am: [report]

Shriekback68: yup, you’re totally right. It does make sense that this type of pairing is more common. I was also surprised by Chelsea’s choice in men! Definitely not who I’d have guessed her to be with.