Inside Sienna Miller and Oli Green’s Whirlwind Romance: The Complete Timeline

Sienna Miller and Oli Green went from a Halloween meet-cute she almost ignored to two kids and a very busy life. Here is how this relationship actually rolled out, with all the little twists you might not have heard about.

How they met (and why she almost waved it off)

They first crossed paths at a Halloween party through a mutual friend. Miller has said her first reaction was basically: this is not happening. Green kept at it and convinced her to grab a drink. Early on, Emily Blunt even tagged along on one of their New York dates and later said she saw a lot of Miller in Green — that same free-spirited, curious, slightly guileless vibe. Not your average third-wheel situation, but somehow very them.

Quick refresher on Miller before Green

Before Oli, Miller had a very public on-off with Jude Law (2004–2011), then dated Tom Sturridge (2011–2015). She and Sturridge share a daughter, Marlowe, born in July 2012.

The relationship, beat by beat

• February 2022: First linked after being spotted on a New York City date.
• March 2022: They are seen leaving Royal Albert Hall together after the BAFTAs, then make their red carpet debut at the Vanity Fair Oscar Party in Beverly Hills later that month.
• April 2022: In an interview, Miller says she froze her eggs when she turned 40, describing the pressure of the so-called biological clock as loud and relentless. Freezing changed the temperature on all that — if another baby happened, it happened, and the looming panic eased.
• August 2023: After pregnancy chatter bubbles up in St. Tropez the month before, she steps out in Ibiza with a visible baby bump.
• September 2023: Bump on full display in an ivory Schiaparelli look at Vogue World: London.
• December 2023: On the cover of British Vogue at 28 weeks pregnant, Miller reveals she and Green just moved into their own place after a stint living at his parents home in West London. She also shrugs off their 14-year age gap — matters of the heart do not follow rules, basically.
• January 2024: She gives birth to their baby girl.
• May 2024: In an essay about a Maldives trip, Miller calls it their first actual holiday as just the two of them — a late-arriving babymoon that felt a little magical, with time to think about each other and the baby about to arrive.
• June 2024: Miller says she did not expect to take Green seriously at first, then fell fast. She also admits she was surprised by his age when they met:

  "F--k! Why are you young? That's so annoying."

  She adds that the age gap has turned out to be a plus — she sees a tangible shift in how Green’s generation treats women, and credits both him specifically and the environment he grew up in.
• December 2025: At the British Fashion Awards, she reveals she is pregnant again, baby No. 2 with Green.
• May 2026: Miller confirms their second baby has arrived, joking that coherent sentences are a stretch on no sleep but she is wildly in love with the newborn.

  "I have a tiny baby next door."

What stands out

The origin story is peak celebrity-normal: a costume party, a reluctant yes, and a friend (Emily Blunt!) as early chaperone. The timeline is equally human — a couple living for a bit at his parents place before finding their own, not taking their first actual vacation together until two years in, and then suddenly they are a family of four. The age-gap conversation could have been tedious, but Miller’s take is refreshingly practical: it mattered far less than the person, and in their case, it has actually helped.