My flatmate was watching Made In Chelsea on Monday and said, “Didn’t Olivia date Tristan three times?” Yeah. Three times. They kept getting back together. Now she’s with someone else. Or maybe two someone else’s? Honestly, Olivia Bentley boyfriend situation is a mess right now.
Here’s what I’ve worked out. Different websites say different things. Some say she’s dating Rory McIvor, an Irish banker. Others say it’s Rory Hamilton-Brown, a cricket player. And some reckon she’s single again. Both blokes are called Rory. Classic Olivia, innit?
Let me try and make sense of this.
Two Different Rorys
So, who is Olivia Bentley boyfriend then? It could be either of these two:
Rory McIvor is an Irish investment banker. Works at Ruffer LLP. In May 2024, Olivia went Instagram official with him. Shared a picture of the two of them at lunch in Chelsea, her kissing his cheek. Just put a shamrock emoji as the caption.
He’s 28 or so; he graduated from Edinburgh University in 2017. They were introduced by mutual friend Cat. Call me Cupid,” Cat commented on the post, which was quite sweet.
But Liv soon deleted that post. Liv only shared one more photo of them, which featured the two wearing skeleton makeup for Halloween. After that? Nothing. No more photos. No mentions. That often means that they’ve broken up, but no one went official.
Rory Hamilton-Brown, who is a former Surrey cricket captain. He was 22 years old when he became the captain, which is mental. He’s 37 and was a rugby player for club Harlequins and England Juniors before cricket. Attended a private school that cost £57,000 a year. Properly loaded.
Olivia’s dating him, according to reports dating back to late 2024. She did drop a hint that she had a new boyfriend on Made In Chelsea, but didn’t add much and kept it dead private. Smart move, given her previous relationships were ripped apart on telly.
So which Rory is it? Or is she with neither now? Nobody knows. Olivia Bentley Instagram hasn’t shown much of either of them lately.
About Olivia
Olivia Bentley age is 29, as she was born on 26th August 1995. She has appeared in Made In Chelsea since 2016. That’s nine years of having your love life on telly for the world to judge.
Olivia Bentley family is loaded. Dad, Keven, is Managing Director at Bentley Group, which specialises in plumbing and electrical services. Mum’s Kate. She also has three sisters – Kinvara, Athena and Cordelia, which are quite posh names.
Their old family estate in Oxfordshire was on the market for £50 million. Fifty million quid. Mental.
She’s the great-great-great granddaughter of the founder of Bentley Motors, Olivia says. The company denied it, though. That was a very awkward situation. Imagine saying that you are related to a famous brand and the company says, “Nah.” She went to Bradfield College. That’s £38,850 a year. I can’t even fathom paying that for school.
What She Does
Olivia Bentley net worth is around £1.1 million. Not bad for 29. She makes money from Made In Chelsea. But she’s also got Olivia Bentley business; she co-founded JOMO London in 2022 with makeup artist Bella Campbell. It stands for Joy Of Missing Out. They sell CBD oils and lubes. Adult wellness stuff.
She’s also a fine art photographer and does nude photography. Had exhibitions in London. That’s her real passion, apparently.
Plus loads of influencer work. Brand deals on Instagram. Love Honey, vitamins, jewellery, and perfume. It adds up.
The Tristan Drama
Before the Rorys, there was Tristan Phipps. That relationship was mental as it went on, off, on, off. They began dating in 2020. Split after a year and a half. They reunited in 2022. Split again in 2023.
Tristan said in an interview that the love was still there, but it didn’t work out. Quite mature, really. No drama. No slagging each other off.
Olivia said she ended it. Called herself “happily single” afterwards. Then started dating Rory McIvor a few months later. So much for happily single.
All The Other Exes
Olivia Bentley boyfriend history is quite long. There was:
- Digby Edgley – dated on and off from 2017 to 2019. Loads of drama on Made In Chelsea.
- Josh Ritchie – the Love Island star. They were on Celebs Go Dating together in 2020.
- Demi Sims – from TOWIE. Olivia went on a date with her on Celebs Go Dating. Surprised everyone.
- Fredrik Ferrier – another Made In Chelsea boy. Ended when he got caught texting about new girl Mimi Bouchard.
- Francis Boulle – her first Made In Chelsea romance when she joined in 2016.
- Sam Thompson – they had a thing early on. Sam’s married to Zara McDermott now.
- Alex Mytton – They slept together in France two days after he split from his ex.
That’s a lot of relationships to have on national telly. No wonder she’s keeping the current one private.
Why She’s Keeping Quiet Now
After having loads of relationships on Made In Chelsea, Olivia’s clearly learned to keep things private. When she mentioned the new boyfriend on the show, she didn’t say his name. Didn’t show photos. Nothing.
Smart move. Her previous relationships became storylines where every argument and every breakup was on camera. That can’t be good for an actual relationship.
By keeping the current one off telly and off Instagram, she’s protecting it. Giving it a chance without everyone watching and judging.
My mate Sarah was on a reality show years ago. Her relationship got torn apart by viewers. Now she refuses to post about her boyfriend at all. Can’t blame her.
Dating in the Public Eye
Dating when you’re on a reality show must be properly difficult. Everything gets analysed. Every Instagram post. Every person you’ve been seen with. Trolls send abuse if they don’t like who you’re dating.
Olivia Bentley boyfriend whoever he is now, has to deal with all that. Dating someone in the public eye isn’t easy. You get photographed. People dig into your past. Your exes get found and interviewed. Mental.
That’s probably why Olivia’s keeping it so private now. She’s done the public relationship thing loads of times. It didn’t work. So now she’s trying something different.
Where Things Are Now
So who is Olivia Bentley boyfriend in October 2025? Most likely Rory Hamilton-Brown, the cricket player. But she’s keeping it so private nobody knows for sure. She might’ve already split from him. Or she might be single. Who knows?
What we do know is Olivia’s learned from her past. She’s 29, has been on telly for nine years, and has had multiple public breakups. She’s worked out that keeping her love life private is probably smart.
Olivia Bentley net worth of £1.1 million means she’s financially sorted. Olivia Bentley business JOMO London is doing well. Her photography career continues. She doesn’t need a relationship storyline to stay relevant.
She’s just a woman trying to find someone decent to date. The fact that she’s on a reality show makes that harder. So fair play to her for keeping this one under wraps.
Whether Rory Hamilton-Brown is still Olivia Bentley boyfriend or whether she’s moved on, good luck to her. After everything that’s been on telly, she deserves a relationship that actually works.
