“Jon Hamm has been quietly dating actress Anna Osceola for a few months” links

Jon Hamm arrives at the Tom Ford: Autumn/Wint...

Jon Hamm is apparently dating his old Mad Men costar Anna Osceola. [Dlisted]
Lady G doesn’t understand the French Revolution. [Jezebel]
George Conway & Kellyanne Conway are still married, shockingly. [Pajiba]
Halsey’s star-print dress is so cute! [JustJared]
Timothee Chalamet & Eiza Gonzalez are a new couple. [LaineyGossip]
The Erdem Resort collection looks very Duchess Kate. [Tom & Lorenzo]
Donald Trump does more to protect dead traitors than living citizens. [Towleroad]
It’s always nice to look at photos of Janelle Monae. [GFY]
Teyana Taylor is the face of MAC Cosmetics. [RCFA]

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31 Responses to ““Jon Hamm has been quietly dating actress Anna Osceola for a few months” links”

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  1. minx says:

    I had to look up Anna Osceola in IMDb…she was the girl with the red ribbon braids in the MM finale. 17 years younger than JH.

    • Anonymous says:

      And she looks really young for her age, which is a bit jarring next to him!

      • derpshooter says:

        Poor Jennifer Weston. Ladies, never jack up your face for a dude. If he makes those kinds of statements, he will break up with you eventually anyway to get someone younger. And you’ll be left with something permanent that you did for him, not for yourself.

    • Sean says:

      Right? I wouldn’t say she was a “costar”. She had a brief walk-on part in the final episode.

    • LidiaJara says:

      Is there any scandal in this timeline? A lot of sites are calling her his “longtime” girlfriend and they were first photographed together in 2017 as far as I know. Granted that’s like 2 years after they filmed together, which was the year he went to rehab and then got divorced.

    • Arpeggi says:

      She’s in her 30s though. At first I too was thinking “Oh gosh, 88, such a baby!” and then remembered that it means she’s 3 years younger than me. Dating a woman in her 30s who’s been working for a while is quite different from a 20yo.

  2. Dutch says:

    Is a person really a co-star when they appeared in one scene in a TV show that last multiple seasons? That elevates this glorified extra to the same level as January Jones, Elisabeth Moss and Christina Hendricks. Osceola was at most a castmate, it’s probably most accurate to describe her as a day player.

    • lucy2 says:

      That is a stretch calling her a costar. From what I remember, she had a couple of scenes at most?

      • Tiffany :) says:

        Technically, if you are in a scene or two with few lines, it is called a “co-star” role. If you are a guest star, you will have multiple scenes and more lines. They are using the technically correct term, even if it sounds wrong. Co-star roles aren’t substantial.

    • Darla says:

      Right? When I first saw the headline yesterday on twitter I think, I was like oh who’s he dating! I figured someone we’d know. She’s not a costar by any stretch.

  3. adastraperaspera says:

    Janelle Monae is amazing! Has anyone else seen the 90s movie “Paris is Burning?” Her styling reminds me of the ball culture–inventive, bold, surprising.

  4. FC says:

    OMG this suit!!!

  5. girl_ninja says:

    Poor man. He looks so uncomfortable in these photos and so much older than Miss Osceola. She’s a cute young woman.

  6. AppleTartin says:

    She’s 32 he is 49, she was on the Mad Men finale she had maybe 1 line with him 5 years ago.

    She looks younger and he has looked 40 since he was 25. I wouldn’t call it cradle robbing with what goes on normally with Hollywood.

    • TeamMeg says:

      You’re right, not cradle robbing by H’wood standards. I’m still disappointed he went so much younger, tho. Typical aging male M.O. “They can, so they do”—with the rare exception.

  7. Lucy says:

    Look, I love Timmy as much as the next person and I know he’s a young adult, but…he looks like a kid next to Eiza.

  8. TheOriginalMia says:

    That picture of Eliza and Timothee is cringeworthy. I mean…is he in his underwear? She went from DJ Cotrona to Josh Duhamel to…that. Yikes.

  9. Tiffany says:

    Emma Roberts is pregnant. Oh boy.

    And didn’t Garrett and Kiki break up because he was not down for having children?

    • derpshooter says:

      More people need to watch the movie French Kiss. “You weren’t afraid of getting married… to her.”

  10. Lua says:

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    ***If you are O negative anyone can receive your blood, you’re so valuable!
    ***If you are O positive you are the most common type, people need you!
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    ***If you’re AB negative, you’re the rarest blood type, go save someone’s life today!

    PLEASE consider donating blood right now ♥️

  11. meh says:

    Jon Hamm has been dating Anna Osceola for about three years. There are photos of them out and hanging out going back at least that long. She now lives with him. They didn’t just start dating.

  12. Tanguerita says:

    Could we please stop talking about how Conways’ marriage is in danger? They are a match made in heaven. They have been playing everyone and their dog for four years, playing both sides. This is the most cynical political double act I’ve seen in my life.

    • Vernie says:

      @Tanguerita: I completely agree. They are playing both sides against the middle. I’m surprised more people don’t challenge their facade but apparently the public would rather be distracted by George’s tweets.

  13. SJR says:

    Jon is not aging well, IMO.
    Poor Jennifer, she was with him for what? 15+ years? She was with him while he was actively drinking, while he was really struggling and unknown, etc.
    He finally hits it big in MM, gets sober and…off he goes.
    I have heard some really unpleasant things about his past behavior.
    He was great in Mad Men but, I have zero interest in him these days.

    Don Draper was an interesting character, the storyline of most of the characters were well written, I eagerly looked forward to each episode. For me, turns out I was a fan of MM, not Jon Hamm.

  14. jferber says:

    His silver suit is killing me. I hate it so much. And he doesn’t look much better in the other one.