There are many things to look back on in life and think ‘yep, probably shouldn’t have done that.’
Drinking a little bit too much red wine on a Sunday night before work, going on a date with someone who definitely should have just been a friend, buying that Zara dress. All regrets that unfortunately, we just can’t take back.
But it looks like Whitney Port, star of The Hills, might just have beaten us all. Her biggest regret? Turning down the opportunity for a one night stand with Once Upon a Time… In Hollywood lead,Leonardo DiCaprio.
She revealed on Monday in her podcast With Whit, "I was nervous. I had never had a one-night stand. I didn't want to be with him alone… Then I lost my chance and it's really one of my bigger regrets in life."
The encounter happened after the stars met in 2009 when DiCaprio confessed he was a massive closet fan of her spin-off reality show, The City. Six months of texting over BBM later (oh, the good old days), and the Hollywood star had invited Whitney on a night out and hinted that she should go back to his afterwards.
Talking with her best friend, Andrea Cuttler, on the podcast, Whitney confesses "He invited me back over to his house and I said 'no.’ I have been dying to tell people this story for ages. I feel like whenever I tell it to friends, no one believes me."
Either way, alls well that ends well - Leonardo is currently dating Al Pacino’s 22 year old daughter, model Camila Morrone amidst rumours that an engagement is on the cards.
Meanwhile, after a multitude of turbulent relationships both on and off screen, Whitney is now married to TV producer, Tim Rosenman, and the couple have a two year old son, Sonny. Everything happens for a reason right?
Revisiting the highs and lows of Leonardo DiCaprio's Oscars journey...
Leonardo DiCaprio Oscars - Grazia
1 of 81994: Leo's first Oscars
It's the start of a beautiful relationship. Leo's first Oscar nomination (for Best Supporting Actor, which remains his only nod in this category) came at the tender age of 19, for his role in What's Eating Gilbert Grape. He lost out to Tommy Lee Jones for The Fugitive, but still had a grand old time at the Governor's Ball after party.
2 of 82000: Enjoying the after party
No nominations for Leo this time, but that's no reason not to enjoy the after party scene, right?
3 of 82005: His first Best Actor nomination
Fast-forward a few years and Leo has netted his second nomination - his first in the Lead Actor category - for The Aviator. Sadly, he loses out to Jamie Foxx, who picks up the award for his role in Ray.
4 of 82007: Another nomination
Would it prove third time lucky for Leo? We all know the answer to this one: the star, nominated for Blood Diamond, lost out to Forest Whitaker for The Last King of Scotland.
5 of 82014: So close, so far
For one hot minute, it seemed that Leo would finally win for his unhinged turned as thoroughly unlikable stockbroker Jordan Belfort in the Wolf Of Wall Street - until Matthew McConaughey rode the waves of the McConaissance all the way to the Academy Awards. And thus, the Internet was saturated with hundreds of 'Sad Leo' memes...
6 of 82016: Leo wins his Oscar
Together at last: at the 2016 Academy Awards ceremony, Leo finally gets a little gold man to call his own, picking up the Best Actor Oscar for his gruelling turn in The Revenant. The competition (Michael Fassbender for Steve Jobs, Eddie Redmayne for The Danish Girl, Matt Damon for The Martian and Bryan Cranston for Trumbo) never stood a chance – it was always going to be Leo's year.
7 of 82016: Our hearts will go on and on
What better way to celebrate Leo's Oscar success than with a hug from long-standing BFF and Titanic co-star Kate Winslet? Cue up the Celine Dion - we're feeling tearing just thinking about it.
8 of 82017: Back for presenting duties
After his big win, 2017 saw Leo invited back to the Dolby Theatre, this time on presenting duties. Having presented Emma Stone with her Best Actress statuette for La La Land, the star was spotted walking offstage with a red envelope, leading some Twitter conspiracy theorists to hypothesise that Leo was to blame for the infamous 'envelope-gate' mix up. Of course, he had precisely nothing to do with it…