He was once the toast of Hollywood – and one of showbiz’s most eligible bachelors – but newly single Orlando Bloom isn’t finding his new single life as much fun as he’d hoped.

While ex-fiancée Katy Perry has been pictured cosying up to a new man (Canada’s former PM, Justin Trudeau, no less!), heat is hearing that Orlando is finding life after their separation far harder than he bargained for.

“When Orlando and Katy broke up, he was sure he’d be able to attract anyone,” a source confides. “But things aren’t going his way. Women don’t take him seriously and just think he’s a bit much – he keeps striking out in the dating scene.”

“He was turned down by Sydney Sweeney, which really stung and left him embarrassed. People tend to roll their eyes when he walks by. He’s coming across as a cringey middle-aged guy, while Katy is thriving and looking happier than ever.”

After nine years together and a four-year-old daughter, Daisy Dove, the pair confirmed their split just after Orlando made his public ‘single man debut’ at Jeff Bezos and Lauren Sanchez’s wedding on July 4th.

Orlando appeared upbeat at the wedding, spotted speaking with Kim Kardashian and strolling in Venice with Sydney Sweeney, his arm around a ‘mystery woman –later revealed to be one of Katy’s former stylists.

Later, word spread that Orlando, now 48, had been preparing for single life long before the break. He was reportedly seen openly flirting in Miami this spring, joining in the launch of a cruise ship and attending the Miami Grand Prix with other recently-single stars like Tom Brady and Timothée Chalamet.

While Orlando cut loose, Katy was hard at work headlining her Lifetimes Tour, which wraps up in December in Abu Dhabi. Despite her exhausting schedule, fans were thrilled when Katy, 40, was photographed at dinner with former Canadian Prime Minister Justin Trudeau, 53, who also attended her Montreal concert just days later.

Now, insiders confirm Katy is positively glowing over the unexpected connection. “She’s giddy and it’s all so new, but Katy can’t think of a more exciting man to be seeing. Politics has always fascinated her, and dating Justin – who is one of the world’s most sought-after politicians – feels like a huge win. After everything with Orlando, this new spark is exactly what she needed.”

Meanwhile, seeing Katy embrace a fresh start with such a high-profile bachelor has left Orlando devastated. “Watching Katy with Justin is a blow to Orlando’s pride,” our source reveals. “He can clearly see how excited she is to move on, and it’s shaken him. He knows Justin has both the charm and looks and he’s struggling with that.”

“He’s reflecting now, realizing he could have treated Katy with more kindness. Seeing her flourish like this is a tough pill to swallow.”

Once a leading man thanks to his roles in Pirates of the Caribbean and The Lord of the Rings, Orlando seemed to have it all – famous exes like actresses Kate Bosworth and Penelope Cruz, and a marriage to supermodel Miranda Kerr, with whom he shares son Flynn, 13.

Orlando has said himself that’s he’s always ‘loved women.’ In a 2020 interview, he talked about the sexual magnetism he felt – and inspired – everywhere he went, revealing, ‘If it wasn’t in my eye, it was probably in theirs [the women he met at parties]. I was a pretty boy, so wherever I went there was a bit of [frisson]. And I loved women.’

Now, though, it’s a different Hollywood for Orlando. “He used to be so confident, but the rejections lately have thrown him off,” says the insider. “He thought women would be clamouring for him at the Bezos wedding, but instead, he’s faced disappointment after disappointment – and now he can hardly get a date in LA.”

“He’s not the blockbuster superstar he was 20 years ago, and while he still sees himself as an A-lister, he can come across as fairly arrogant and that’s been a turn-off to a lot of the girls he’s going after.’

Katy and Orlando have promised to lovingly co-parent their daughter and even managed a recent family trip to Capri. But friends noticed Katy was visibly struggling, at times appearing heartbroken during the yacht vacation and breaking down in tears at her last Australian show.

Now, those close to them say Orlando is feeling the fallout from his past mistakes. “Many women feel Katy was wronged, and Orlando’s recent behaviour hasn’t done him any favours. Sympathy for him is at a low.”

“He’s suddenly just another single guy in Hollywood, realizing he’ll have to reset his expectations. He’s still clinging to the confidence of his youth, but the years have caught up with him – and his enormous ego isn’t exactly helping him with the ladies!’