Rosie O'Donnell and Angelina: It would've never worked!

Recently, Rosie O'Donnell revealed that she very nearly, did something, with Angelina Jolie. Rosie's implication was that she and Angelina nearly dated. Or rather, Angelina gave Rosie her phone number and they had several phone conversations. But per usual, if Angelina Jolie's name is mentioned, the story takes on a bigger life, which may have been Rosie's intention, since she's launching a new radio show next month.

At any rate, this 'revelation' got me to thinking, which is likely the opposite of what most men are doing today. Rosie O'Donnell and Angelina Jolie is not the sapphic combination they were banking on, and for that matter, it's not particularly appetizing to the 'would go gay for Angie' crowd either. But it's interesting to come up with reasons why this coupling would not work. Here's a brief list:

• The age difference - Thirteen years separate Rosie and Angelina versus the twelve that separate Brad and Angelina; however, the decades make a difference. Assuming that the phone number was given to Rosie in the late 90s, Angelina was around 21-22 years old, while Rosie was in her mid thirties. It was well-documented that Angelina was going through her wild child phase, while Rosie was taking care of her son, Parker, and very closeted. Could Rosie have handled Angelina's youthful impetuousness? Possibly, but then again, Rosie has a strong personality, bordering on bullying. Would Angelina interpret Rosie's strength as strength or rebel against, as she did nearly everything. Versus, 30-something Angelina, who is more comfortable in her skin and is with 40-something Brad Pitt, who seems pretty mellow about everything.

• Rosie was closeted - Brad Pitt, seemingly, broke his neck getting the hell away from Jennifer Aniston in order to be with Angelina; would Rosie have crashed through the closet door? I think... no, given how invested she was in her talk show. This woman waited until the tail end of her show's run to tell her audience the truth. Would Angelina have been willing to be kept in the shadows in order for Rosie's career to flourish? And for that matter, would that have even been possible, given that she was a lightening rod of controversy even then?

• Personality clashes - Angelina claimed that she and Colin Farrell were too much alike to be together. While Rosie and Angelina aren't alike, on paper, they are both polarizing figures. As I mentioned before, Rosie is a bit of a bully, whereas Angelina, though provocative in her interviews, doesn't attack other people. When Rosie have public feuds, she's usually the person who starts them. When people feud with Angelina, it's usually one-sided, since she rarely participates. Would Rosie stand for this? Would she perceive Angelina's silences as weakness? Or would she escalates the feuds, in defense of her love?

• Rosie's anti-gun stance - In recent years, Angelina has starred in a lot of high-octane, gun brandishing, action flicks - films which Rosie usually wags her finger at. If this coupling happened in the late 90s, would Rosie have tried to dissuade Angelina from tackling action flicks? Would Rosie have gone on tirades similar to the Tom Selleck ambush and anti- Fight Club rants for Angelina's films? If not, wouldn't that have emphasized Rosie's selective outrage?

• The intimidation factor - Angelina is considered the sexiest woman on planet Earth. Ten years ago, she was considered the sexiest woman on planet Earth, but she was also kinda kinky and dark. Rosie, at best, is stocky. Could Rosie have handled the eyefcuking that Angelina, undoubtedly gets? And one on one, would Rosie have been confident enough to be intimate with Angelina. Would Angelina have been sexually satisfied?

• The showtunes - Who knows if Rosie bursts into showtunes at home like she did on her talk show, but could you imagine the looks she would get from Angelina?

• The chin hair - It's widely known that when Angelina goes on her UNHCR trips, she goes hard core - meaning no baths, makeup, etc. So B.O. wouldn't scare Angelina off; but would Rosie's fascination with bodily functions? I refer to Rosie's past obsession with her chin hair. An obsession with resulted in her growing it out and putting beads on it. Now every woman has that strange chin hair that is too thick and too dark to ignore. Most of us pluck it out - Rosie... not so much! Much has been made about Brad's chin hairs, but they're hairs, not a single strand. Angelina has seen a lot of sights, but would little experiments like that make her stomach bubble?

• Rosie's friendship with Madonna - Much has been made about the supposed feud between Madonna and Angelina, but the emphasis has been on the African adoptions and charitable projects in specific regions in Africa. But Madonna is an alpha female of the highest order. Angelina is perceived as an alpha female, but she doesn't work as hard as Madonna to earn that rep. But there is a competition going on, even if it is one sided.

• Acting - game to Angelina
• Sex appeal - game to Angelina
• Will go gay/straight for factor - game to Angelina

Actually, I think that gay/straight factor is what sticks in Madonna's craw. Madonna was probably the first female star to openly admit to her bisexuality, but that admission kinda fell flat. It always felt like a tactic to titillate the masses. Her Sex book became the symbol of Madonna's detached, clinical take on sexuality. Angelina, on the other hand, generated a lot of buzz when she revealed her bisexuality. In fact, that admission made the 'will go gay/straight for' phenomenon possible. People can picture Angelina having sex and having a hella good time at it. In terms of the sexual revolution, Angelina did more by just being than Madonna who was just doing. Certain things should come easily - Madonna apparently doesn't.

Ultimately, an ultimatum, from Madonna, would've come down. Would Rosie have been strong enough to say no to Madonna?

So many questions and possibilities. Fortunately, the pairing didn't happen; therefore my high opinion of Angelina continues.