Jon Hamm, 52, and Anna Osceola, 35, married in Big Sur this weekend

In February, Jon Hamm got engaged to Anna Osceola, his girlfriend of “two years.” I questioned the timeline, especially given that Hamm and Osceola likely met in 2015/16 and probably started dating in 2017. But no matter – the point is that Hamm spent 18-plus years with Jennifer Westfeldt before they fell apart, and Hamm married his next serious girlfriend. They were married in Big Sur, which is likely where they met during the final season of Mad Men.

Jon Hamm and Anna Osceola are married, PEOPLE can confirm. The Mad Men and Confess, Fletch costars tied the knot on Saturday, according to TMZ.

The couple wed at Anderson Canyon in Big Sur — the same place where the Mad Men finale filmed — where they were joined by various celebrity pals, including Billy Crudup, Paul Rudd and Tina Fey, the outlet reported.

TMZ said the couple’s walkup song was the theme to the 1967 James Bond film You Only Live Twice.

Representatives for both Hamm, 52, and Osceola, 35, did not comment to PEOPLE.

[From People]

I’m including some social media photos of the wedding below. While the locale looks beautiful and rustic, Hamm wore a traditional tuxedo and Anna wore a lovely silk/satin wedding gown, like they were getting married at the Ritz. He doesn’t seem like a Big Sur-wedding kind of guy, but what do I know? They both looked good on their wedding day. I guess Jennifer Westfeldt didn’t attend. Imagine spending close to two decades with someone and the breakup was so bad, you never see each other again or speak to each other or talk about one another. Yikes.

Photos courtesy of Avalon Red.

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30 Responses to “Jon Hamm, 52, and Anna Osceola, 35, married in Big Sur this weekend”

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  1. pinger says:

    Love the dress and good for her for getting him to commit; good age difference so as not to be traded in down the road. Congrats to them if it lasts.

  2. Duchess of hazard says:

    Damn. He didn’t want to marry – the woman before. Harsh.

    • Eurydice says:

      Like from When Harry Met Sally – “All this time I’ve been saying that he didn’t want to get married. But the truth is he didn’t want to marry me.”

    • Kara says:

      Can we stop with this sexist stuff? Jennifer Westfeldt said in interviews during their relationship that she wasn’t interested in marriage or kids. The whole trope that only the woman is angling for the ring is so tired.

      • SquiddusMaximus says:

        YES. The idea that she was somehow victimized is misogynistic speculation.

      • MipMip says:

        Yes! Why do so many intelligent women STILL see marriage as the be-all-end-all? JW said herself that she didn’t want marriage or kids. Why are people on here pitying her? They still had an 18-year relationship, that’s not nothing. The tone around all this makes it seem like that counts for nothing because they never had a big party and signed a piece of paper? Nah.

        And FWIW JH and JW do still communicate? At least they did for a while after their separation. I can’t blame any of them for her not being at the wedding g it’s just an awkward situation.

  3. Peacock says:

    How do we know they aren’t in contact? Feels a bit off that people are being so sympathetic to Jennifer – they broke up 8 years ago for reasons we don’t know, and she could be out there living her best life not caring one iota about an ex from nearly a decade ago getting married, she may not be welcoming this pity party people seemed determined to throw for her

    • Teddy says:

      Agree. She’s the one who didn’t want to get married and she broke it off. they both talked about continuing to be and good to each other and imho the silence speaks to that.

      • Bingo says:

        I listened to an interview years ago and he always talked fondly of her. She supported him for years when he was struggling as a cater waiter trying to break into the business. He was already 36 when Mad Men first aired. And even then he only got the part when Thomas Jane passed on it. He always seemed grateful for the years they were together. Except for the later drinking and cheating part when she dumped him. And like everyone has posted Jennifer had no interest in marriage or kids. She wasn’t pining for it.

    • tealily says:

      And why would she attend the wedding? I can’t think of something I’d like to do less than attending my ex’s wedding, except maybe to have my partner’s ex attend our wedding.

  4. Seraphina says:

    Congrats to the couple. That wedding dress needs some bodice intervention. I see it on so many beautiful women on the red carpet too. Beautiful bodies and the bodice does them no favors.

    • Josephine says:

      That was my thought as well. I just want to tug it up and together – it’s not flattering at all, makes her look wide and she’s obviously not. I also thought her hair was not very nice for the big day. But the setting was lovely and it looked laid back and fun, which is nice to see.

  5. JessicA says:

    He did an interview with Howard stern which I saw highlighted on a blog and he talked about how he has done intensive therapy in order to have more fulfilling relationships and expand his life with a wife and kids, etc etc. He said it has been years of work, so if that is true, kudos to him and I hope it works out for them.

    • Noo says:

      With the horrific accounts about how he abused fellow students in the hazing I think he would definitely need a lot of therapy. Just to be a normal non-abusuve human, let alone a decent husband.

  6. MM says:

    Last episode of mad men aired May 2015 – they likely met early 2015 or late 2014. Almost a decade.

    • Bingo says:

      They met on the set of Mad Men she was in a small scene of the last episode. They started dating in 2017 two years after he and Jennifer broke up. Unless she was on the side until they went public. It was well known he was cheating on Jennifer every chance he could. And remember Anna if he cheats with you he will cheat on you.

  7. Chaine says:

    That dress is hanging in for dear life!

  8. girl_ninja says:

    Good for them. Lovely gown.

  9. Isa says:

    The top of the dress looks too small. Like she’s so stuffed in there it’s pulling apart.

  10. Twin Falls says:

    Big Sur is gorgeous. Looks like it would be a very romantic place for a wedding. Best of luck to them.

  11. Sean says:

    17 year age difference. It makes me think of when Don married the much younger Meghan with Joan and Peggy having a gossip session about it.

  12. PeanutButter says:

    I wonder why he finally decided to get married. Fatherhood?

  13. HeyKay says:

    Good Luck to her. He is no prize.

  14. Scout says:

    Still horrified at the hazing rituals he was involved in. I think someone died? I will never look at John Hamm the same way again.

    • Bingo says:

      No one died but it was a violent hazing incident. A google search will give the details. Jon and the men involved were arrested and pled guilty to misdemeanors. The assault charges were dropped. He got probation, the fraternity was shut down and Jon left the college. His parents also both died of cancer in the middle of it all. The man also sued them in 1991. It is a shame Jon downplays what happened and distances himself from responsibility.

      • Beeks says:

        I went to to school with him. His mom actually died when he was 10. His dad died when he was 20 and in college. Three different couples (parents of his three closest HS friends) basically raised him. He actually thanked them when he finally won the Emmy.

  15. Jenn says:

    Well, hats off to them, and I can’t believe Deux Moi was right about something