Thanks to a reader called Ruth who sent me this Olivia Wilde throwback yesterday which… seems in hindsight really prophetic. 

First a recap: Olivia Wilde and Jason Sudeikis started dating in 2011. He proposed in 2013 and they broke up in 2020, after seven years of engagement. When exactly they split is now in dispute as sources presumably in Olivia’s camp initially made it seem like they were done a year ago and Jason’s sources came out last week to challenge the timeline, claiming that Jason only found out that Olivia wanted out of the relationship in October, after she’d been working with Harry Styles for a few weeks. 


It’s also possible that… both versions of the timeline are true in that … well… have you ever heard of a “soft” breakup? Or been through one? It’s not quite “let’s take a break”, but more like a slowwwww back-away. Usually in these cases, one person wants the breakup more than the other so they start floating the idea softly. “Something’s missing”, or “I just don’t feel like it’s been the same between us”, “I still love you but …” so it’s not a breakup, yet, but it is a buildup to a breakup, to give the other person time to confront the possibility over time. The other person, however, doesn’t hear it that way. They hear it as, “we are going to work through this rough spot” and “if it was over s/he/they would have told me, there’s still a great chance for us to make it”. And then when the other person actually moves on, they feel blindsided. I’ve been on both ends of this situation. And I’ve seen all the ends of the situation happen to others. Nobody ever agrees on what was agreed on because they totally had their own interpretations on what it was to be agreed upon in the first place. I wonder if this is what’s going down between Olivia and Jason. This is not to say that she didn’t cheat on Jason with Harry – and if that’s really what went down, yes of course, it’s a sh-tty thing. It’s just… in the two stories that PEOPLE published about Jason last Friday which I referenced in my post yesterday, sources close to him still seem to be leaving open the possibility of them reconciling, or at least putting it out there that Jason still has “hopes to repair things” between them. 


But anyway… now to the throwback that Ruth sent over. It’s from 2012 and Olivia was part of Glamour magazine’s event, “These Girls”, a series of mostly comedic monologues delivered by prominent female entertainers including Amy Poehler, Rashida Jones, Aubrey Plaza, Ari Graynor, and more. During her monologue, Olivia talked about her first marriage and when she knew it had to end. Per Vulture:

“I felt like my vagina died,” she said. “Turned off. Lights out … And you can lie to your relatives at Christmas dinner and tell them everything on the home front is just peachy. But you cannot lie to your vagina.”

She went on to recount that after she got out of the marriage, she had a lot of sex but after a while, it started to feel empty and lonely. And then she met Jason and fell in love. He was in the audience at the time. This, remember, would have been a year after they started dating and a year before they got engaged. Olivia then continued to ruminate about monogamy, about love and commitment. Again per Vulture, “Wilde said she was happy in her new relationship, except for the nagging worry that the hot monogamy (“We have sex like Kenyan marathon runners”) might not last. So, in efforts to protect herself, she outlined the rules for Olivia Land, a relationship Utopia.”


This kicked off a bit about how Olivia Land would work…and the specificity of it is why Ruth messaged me about it: 

“In Olivia Land, relationships can legally only last seven years, without an option to renew. That way it never goes stale. Can you imagine, if we only had seven years? We’d be so nice to each other, so kind, and appreciative and enthusiastic, like we were eating a really expensive bowl of pasta!”

Seven years is how long she and Jason were engaged. 

Remember, this was for comedy but as is often true of comedy, she was (27 or 28 at the time and) interrogating her ideals and values, her perspective on sex and love and relationships. As she later told Vulture: “Ultimately, the monologue was supposed to suggest that Olivia Land doesn’t work either”. And she ended her monologue with a question mark, because ultimately … has anyone figured out the secret sauce of love and longevity? The only thing, at that time, she was sure of? The vagina is not wrong: 

“Sometimes your vagina dies. Then you know it’s time to go. There’s no reason to sacrifice your womanhood and femininity for some sort of weird feeling of responsibility to something that may not be right. I feel like far too many women do that.”

If she gave another monologue today, how would it change from the monologue she wrote then? 

Thanks Ruth!