Rosie O’Donnell says she missed her chance to date Angelina Jolie

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Rosie O’Donnell admitted that she and her wife/partner Kelli Carpenter were having relationship trouble last week in an interview to USA Today. Since that interview, gossip has been going around that Rosie and Kelli are pretty much done, but it seemed like Rosie wouldn’t be confirming the split either way. That is, until Rosie went on the Howard Stern Show yesterday. Sidenote: who knew that Howard and Rosie were friendly enough for her to appear on his show? I didn’t.

Anyhoodle, Rosie came close to confirming that she and Kelli are done, but that they are still committed to co-parenting. One of the more interesting revelations was about Rosie and her friendship with Angelina Jolie. Rosie says that before Angelina got together with Billy Bob Thornton, she and Angelina “talked on the phone two or three times, but that was that. There was a tentative plan to have dinner that never came through. I was a little afraid of her. She’s scary in a sexual kind of way.” Rosie also admitted that she has “dream about her a lot still.” I always knew that Rosie and Angelina were friendly, but I had no idea that they were this friendly. Well… Angelina could have done worse. And she did, on occasion.

In an interview last week, Rosie O’Donnell promised she wasn’t going to talk about her assumed split with longtime lover Kelli Carpenter. But that was before she sat down with old pal Howard Stern on Monday, when the former daytime Queen went as far to say the couple was kaput without actually saying it.

O’Donnell told Stern she and Carpenter had “different styles of living” and have “come to a point where we are seeing [if] what will make everyone happiest is maybe to not live together, but continue to parent.”

The couple married in San Francisco in 2004 and have three adopted children (Parker, 14, Chelsea, 12, and Blake, 9) as well 6-year-old Vivienne, whom Carpenter carried.

When Stern pressed for more info behind her relationship woes, O’Donnell offered up a dish of TMI: “Kelli and I have a lot of issues and sex wasn’t one of them.”

O’Donnell told Stern she isn’t thinking about dating anyone. “I’m not a trier,” she admitted.

In an interview with USA Today a week ago, the former ‘The View’ moderator said she and Carpenter are “working on our issues” and that “those are the only words I am ever going to say. Ever.”

The National Enquirer reported in August that Carpenter had moved out their home and into Manhattan.

Since it was becoming clear she wasn’t going to fully open up on her woes, Stern steered his convo with O’Donnell to the star’s love life before Carpenter. O’Donnell admitted she had a phone fling with Angelina Jolie, before she hit the big time.

“We talked on the phone two or three times, but that was that. There was a tentative plan to have dinner that never came through,” she said.

“I was a little afraid of her. She’s scary in a sexual kind of way.”

[From PopEater]

In the Stern interview, Rosie also talked about those “Oprah Winfrey is gay, with Gayle” rumors. Rosie said: “When they did that road trip, that’s as gay as it gets.” While I think that’s slightly funny, I disagree. I kind of believe Oprah when she says that if she and Gayle were gay, she would tell us. At this point, if Oprah was gay and she told all of those Oprah-worshipping soccer moms to be gay, they totally would.

Photos credit: WENN.com

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44 Responses to “Rosie O’Donnell says she missed her chance to date Angelina Jolie”

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  1. Trillion says:

    And here we see Angelina wiping a tear from her face after laughing for 10 minutes solid…

  2. barneslr says:

    Yeah. Because that hideous, shrill troll would ever have a glimmer of a chance with someone as attractive as AJ.

    In your dreams, Rosie.

  3. Kaboom says:

    Lucky Angelina.

  4. MJ says:

    Angelina seems like a nice loving person but I don’t get why a lot of men and women fantasize and are obsessed with her.
    With Rosie talking like that I do believe she and Kelly are over or else she would be more careful with her words. I wonder why they split the kids up- with Kelly
    taking only the youngest one. That house must have been very divided.

  5. Firestarter says:

    RIIIIGHT! From being with someone like Jenny Shimizu, to Rosie! Not likely, but good attempt at trying to revive your career as a comedienne!

  6. Lem says:

    shoot me too!! I missed Johnny Depp and Health Ledger. I missed Selma Hayak and Sofia Vergara.
    Good news Rosie. there’s probably still a chance with Megan Fox 🙂

  7. lulu says:

    talking to someone three times on the phone does not = fling. This woman grates on every single nerve in my body.

  8. Codzilla says:

    No, Angelina could not have done any worse than Rosie. She (Rosie) is about as bottom of the barrel as it gets.

    LOL @ Trillion — no kidding.

  9. cara says:

    THAT is the best pic I’ve ever seen of AJ.

  10. Praise St. Angie! says:

    “Yeah. Because that hideous, shrill troll would ever have a glimmer of a chance with someone as attractive as AJ.”

    why not? Billy Bob did, and he could be described the same way.

    not that I believe this at ALL, but Jolie doesn’t seem the type to dismiss someone based on physical attractiveness.

  11. Oenix says:

    Rosie has as much chance winning the lottery…

  12. Mel says:

    And the sad thing is, this angry, bitter harpy knows that Angelina will never publicly address these ridiculous claims, giving Rosie the last word.

  13. KateNonymous says:

    Well, maybe she can get together with Megan Fox.

  14. Melanie says:

    Howard Stern loves Rosie ODonnel because she is a very forthcoming guest. She’s very honest and forthcoming guest,which is exactly what he wants.

  15. Trillion says:

    Welcome back Codzilla!

  16. Firestarter says:

    LOL@Praise St. Angie!

  17. cee says:

    Why does anybody looking for publicity use Angelina Jolie’s name. It happens over and over again. Angie is just trying to live her life with Brad and the kids. Leave her be. And Rosie is really stretching. Perhaps all Angie really wanted to do was talk? Give me a break Rosie and Angie.

  18. Kim says:

    I heard that Kellie moved out with Vivian , i wonder why she only took her bio kid. As for Rosie she claimed this happened before AJ hit the big time so I guess AJ was 21 or 22. I think she won the Oscar when she was 23. Help last week I spoke to a lesbian twice on the phone,does that mean we are dating?

  19. Angelina is sexy says:

    Can’t blame Rosie for trying, Angelina is mouth watering gorgeous. Simply love Angelina and I’ve been married to a man for 17 years. She’s yummmmmy! Something about Angelina just turns me on.

  20. June says:

    No wonder Kellie left. Rosie’s marriage is breaking up and all she can mention is that she missed having a fling with Angelina Jolie. What does Angelina Jolie have to do with this picture?

    Rosie does not say she loves her wife and hope they can get back together, but she missed having a fling with Angelina Jolie. LOL

    Sorry Rosie, Angelina is happy with Brad and her six little ones. She has an amazing life, seems to be enjoying her life , seems to really enjoy being a mother and partner to Brad.

  21. June says:

    If Rosie is dreaming about Angelina, maybe she called Kellie, “Angelina” during their lovemaking? LOL

  22. GatsbyGal says:

    I honestly believe that if Oprah were gay, she would never tell the public. She’d take it to her grave.

  23. wow says:

    If I were a lesbian, I’d be pretty annoyed that any other lesbian to take normal things like talking on the phone or going out to dinner with you as a FRIEND to somehow mean they are into you sexually.

    I’m not saying Angelina couldn’t have been into Rosie because of her looks or anything. I’m just saying it must be annoying for lesbians when this happens.

    It’s annoying in general when someone miscontrue your friendly nature as intentions to want to date you.

  24. thepickle says:

    It’s like when that ugly guy becomes your ‘therapist’, always there for you with that soothing understanding “uh- huh, and then what baby?”…but really you know he’s just trying to get in your pants at the end of the day. And then in exchange for therapy, you get f87ked. Good for Angelina that she didn’t fall for That!

  25. Charity is Chic says:

    Don’t worry Rosie, you’ll get another chance.

    If she thought Billy Bob was hot and she’s in the process of turning Brad into Billy Bob 2.0 I can’t see why she’d turn down Rosie.

  26. Kim says:

    I saw pics of Rosie hugged w/ another woman in Miami. They will be in the tabs I saw them on ET last night it looks like she has moved on.

  27. cakes says:

    Angelina Jolie is absolutely gorgeous. I would go gay for her lol.
    @ wow- not just for lesbians but for straight people too. It sucks having the “Im not into you, Im just friendly and outgoing” conversation.

  28. MeowBea says:

    WOW In your dreams Rosie!!!
    @ thepickle Really?? STOP going to therapy!!!

  29. Codzilla says:

    Thanks Trillion 🙂

  30. birdie says:

    “When they did that road trip, that’s as gay as it gets.”

    @ Kaiser I think you might be interpreting this a bit too literally… I take it more as, they took a road trip together and that’s as gay as their relationship ever got. Meaning they aren’t really gay, but they’ve done some gay-esque (coining my own word here) things together. This would fit in more with Rosie’s sense of humor, she likes to push boundaries but I’ve never taken her as the type to try and hurt people maliciously or “out” closeted celebrities. Didn’t she defend Clay Aiken & Lance Bass when people like Mario Lavendera went after them?

    It seems like every celebrity tries to talk about Angelina in interviews these days! It’s as if they will somehow become more interesting by throwing in their six-degree connection to the Brange brand.

  31. Kaiser says:

    Birdie – Rosie said the “that’s as gay as it gets” thing, not me.

  32. Westender says:

    Wonder what Oprah thinks of Rosie’s interview? Guess Rosie will not be on the Oprah show anytime soon!

  33. birdie says:

    Kaiser, sorry I didn’t mean to sound like I was putting words in your mouth. I know Rosie said it… My point was that sometimes humor doesn’t translate well and there is more than one way the statement could be interpreted. To me it sounds like a joke, not a literal confession that yes, Gayle and Oprah are gay. Maybe they are gay, and maybe Rosie knows something we don’t, or maybe she has no idea and was just joking about the whole thing.

  34. Botox brad says:

    Angelina is free bird. can’t wait for her to be single again to see who she dates.

  35. coucou says:

    The laughing pic of AJ was probably taken while she was listening to Rosie on the Stern show…and what is up with the mohogany spray-tan? Egads…

  36. TwinkleToes says:

    Oh come on, haven’t we all teased a lesbian at some times in our lives? When I was young and drunk, it was a sport. Learned quickly that they will pursue you relentlessly and then it got dangerous, so I stopped. I wouldn’t dream of toying with anyone’s feelings today. I’ve grown up and so has AJ.

  37. hater from siloam springs says:

    W
    I
    S
    H
    F
    U
    L

    T
    H
    I
    N
    K
    I
    N
    G
    !

    Actually, I missed my chance to date Angelina Jolie, too — I was never a bulemic lesbian who liked to cut herself. I regret it every day.

  38. sarah says:

    I heard the whole interview. She didn’t say Oprah was gay. She just pointed out that she never goes with Stedman on these roadtrips. She just said it seems like the main relationship is between Oprah and Gayle. But she also said that she doesn’t think they’re gay. Not that there’s anything wrong with that 🙂

  39. LolaBella says:

    …and so Rosie’s quest to remain relevant continues…

    Does anyone else find the timing of this ‘revelation’ convenient…her arch nemesis Donald Trump’s name is in the headlines with his daughter Ivanka’s wedding.

    Expect a Donald Commentary on this on TMZ in 4-3-2…

  40. Bete says:

    I don’t think that Oprah and Gayle are gay, but America is always obsessed with sex, thinks with the sexual cap on first. They are more like sisters. But everyone prefers the lesbo caper.

  41. Merridith says:

    They are both totally nuts and need mental help they would have been perfect together, except for all the disfunctional children with their combined child collecting and double mental illnesses, plus rosie’s drinking and ang’s druggin would have created.

  42. crash2GO2 says:

    @TwinkleToes – I have to say that is something I have never done.

    Sounds scary as hell. :O

  43. syffitf says:

    Rosie O’Donnell says she missed her “chance” to date Angelina Jolie

    FTFY

  44. Crashadia says:

    birdie — risk-gay!!!!