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It started with a kiss at a Halloween party back in 2021. Simple enough, right? Except for Sienna Miller, nothing is ever quite that simple when the paparazzi are lurking. When she first met Oli Green, she didn't exactly have "find a boyfriend fifteen years my junior" on her bingo card.
In fact, she thought the whole thing was kind of absurd.
She's been incredibly blunt about it in interviews, basically saying she told him, "Why are you so young? It’s so annoying." But Green, a model and actor who’s arguably best known for a stint in The Crown, didn't back down. He put in the work, convinced her to grab a drink, and now, here we are in 2026, and they’ve become one of the most low-key stable fixtures in the messy world of celebrity dating.
The Red Carpet Reveal That Reset the Clock
If you follow the "Fashion Awards" circuit, you probably saw the photos from late 2025. Sienna walked onto the red carpet at the Royal Albert Hall and didn't need a press release to say a word. The sheer white Givenchy gown did all the talking.
She’s pregnant. Again.
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This marks her second child with Oli Green and her third overall (joining big sister Marlowe, whom she shares with Tom Sturridge). It’s a bit of a "full circle" moment because it was only in early 2024 that the world saw the first photos of them pushing a pram in West London with their first daughter. They still haven't publically released that little girl's name, by the way. They’re protective like that.
Let’s Talk About the 15-Year Gap
People love to obsess over the numbers. She’s 43; he’s 28. In the grand scheme of Hollywood—where aging actors frequently date women who weren't born when their first movie premiered—the scrutiny Sienna faces feels a bit lopsided.
She’s called it out herself, labeling the judgment as "one-sided" and "sad."
Honestly, it’s refreshing to see a woman in the public eye just... not care? She’s pointed out that Oli’s generation (the elder Gen-Z/young Millennial cohort) actually has a much more level-headed perspective on gender dynamics. According to Sienna, they grew up on a "more level playing field." He doesn't see her as a trophy or a relic; he just sees her.
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Why Oli Green Actually Works
It’s easy to dismiss a "younger boyfriend" as a mid-life whim, but Oli Green seems to have a different frequency. Even Emily Blunt—Sienna’s close friend and professional "vibe checker"—vouched for him early on. She supposedly went on one of their first dates just to see if it was legit. She saw them together, realized the chemistry was "beautiful," and basically snuck out the back to let them be.
- He’s established: He’s not some random hanger-on. He’s been the face of Burberry and Gap.
- The Crown factor: Playing a role in one of Netflix’s biggest prestige dramas isn't a bad resume builder.
- Stability: While Sienna's past relationships (we all remember the Jude Law years) were high-drama, this one feels... quiet.
Navigating a Blended Family in 2026
The transition hasn't been a total fairytale, though. Sienna has been open about the fact that her eldest, Marlowe, had to do some adjusting. Bringing a new partner into a pre-existing family unit is always a minefield, let alone adding a new baby (and now another on the way).
But if you look at the candid shots of them at the 2024 Cannes Film Festival or just wandering through London, there’s a sense of cohesion. They aren't trying to sell you a "perfect family" brand. They just look like people trying to figure out the logistics of school runs and diaper changes while dodging long-lens cameras.
What Most People Get Wrong About Them
The biggest misconception is that this is some rebellious phase for Sienna. It’s been five years. In "celebrity years," that’s basically a golden anniversary.
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They’ve modeled together for Frame denim and supported each other at every major gala from the Met to the BAFTAs. They aren't hiding, but they aren't performing either. There’s a distinct lack of "look at us!" energy on their social media—or lack thereof.
The Realities of Motherhood at 43
Sienna’s second pregnancy with Oli has reignited the conversation about "older motherhood." She’s been very transparent about freezing her eggs in her late 30s, taking the pressure off her "biological clock." It’s a move that more women in the industry are making, and her openness has actually helped de-stigmatize the process for others.
She isn't pretending it's easy. She isn't pretending the age gap never crosses her mind. She’s just living it.
Actionable Insights for Following the Journey:
- Watch for the Birth Announcement: Given their track record, don't expect a glossy magazine cover for the new baby due in 2026. Keep an eye on candid "paparazzi" walks in West London; that’s usually how they "announce" things.
- Check Out "Horizon": If you want to see Sienna’s latest professional work while she balances this pregnancy, her role in the Horizon saga is where she’s been putting her creative energy.
- Re-evaluate the Gap: Next time you see a headline about a "toy boy," look at the longevity of Miller and Green. Five years and two kids in, the "absurd" label she initially gave the relationship clearly doesn't apply anymore.
Their story is a reminder that the "rules" of dating are usually written by people who aren't actually in the room. Whether it's a Halloween party kiss or a red-carpet pregnancy reveal, Sienna Miller and Oli Green are doing things on their own timeline, and honestly, it seems to be working out better than anyone expected.