By Grace Hatchell
There are mistakes.
There are big mistakes.
And then there’s accidentally setting up your college boyfriend with your high school bully.
That, ladies and gentlemen, is what I would call an oops.
Fortunately for Olivia Raine Atwood, it also makes rather good material for an Edinburgh Fringe show.
Olivia is back at the Fringe with OOPS, running at the Gilded Balloon Teviot until 30 August, and if you think your own dating history is complicated, this might make you feel considerably better about it.
You see, Olivia doesn’t merely have opinions about dating.
She’s a professional matchmaker.
Yes, an actual one.
Her 9-to-5 involves finding love for other people, and apparently she’s rather good at it.
Most of the time.
There are questionable dating photographs to contend with, gentlemen in their seventies hoping to date women in their thirties and, every now and again, a match that perhaps should have remained firmly unmatched.
Which brings us back to the boyfriend and the bully.
OOPS tells the story of how Olivia accidentally matched her college boyfriend with her high school bully.
The press release helpfully describes this as being a little like Ron setting Hermione up with Malfoy.
I don’t remember that particular chapter of Harry Potter.
Probably for the best.
Olivia Raine Atwood splits her time between Los Angeles and New York and has a fairly impressive collection of jobs to her name: comedian, matchmaker, writer and fitness instructor.
Good grief.
I have one satchel and needs a sit down by lunchtime.
Her previous work has attracted attention from publications including New York Magazine, British Comedy Guide, Time Out New York and Vulture, while her first show, FAKING IT, went on a world tour in 2024 following her Off-Broadway debut the previous year.
And Olivia is certainly no stranger to Edinburgh.
In 2025, she performed two shows back-to-back for 24 days, with just 25 minutes between them.
Twenty-five minutes!
I’d barely have time to find my sandwiches.
This year she’s concentrating on OOPS, which originally debuted in Hollywood in June 2025 before receiving critical attention in Los Angeles, New York, Edinburgh and London.
Theatre Village has already been along to see Olivia at this year’s Fringe, but if she’s somehow escaped your Fringe schedule so far, there’s still time to catch her.
OOPS continues at 2.30pm at Gilded Balloon Teviot’s Billiard Room until 30 August, with 18 August as a day off. The show runs for 60 minutes and has an age guidance of 12+.
So, if you’re looking for an afternoon involving dating disasters, questionable romantic decisions and a professional matchmaker admitting that even she occasionally gets things spectacularly wrong, pop OOPS onto the list.
And if you’re currently single, take some comfort from Grace:
At least nobody has accidentally matched your ex with your school bully.
Hopefully.
Olivia Raine Atwood: Oops | Edinburgh Festival Fringe
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