The Pirates of the Caribbean actor was spotted cosying up to Hollywood's most famous bachelorette at a star-studded party hosted by celebrity hairdresser Ken Paves in Los Angeles on Friday.
Burgeoning romance? Orlando Bloom and Jennifer Aniston cosied up at a star-studded party in LA on Friday night
While he was surrounded by a bevy of beauties, including Desperate Housewives' star Eva Longoria and Jennifer's best friend Courteney Cox, it was Jennifer, 39, who really caught his attention.
Insiders have said that while the 31-year-old Orlando has been casually linked to Victoria's Secret model Miranda Kerr, he has been harbouring a rather strong crush on the former Friends star in recent times.
Man of the moment: Orlando, with Eva Longoria and Courteney Cox, reaches out for Jennifer, who has her eyes firmly planted on him
The pair first met during the filming of the 2004 movie Troy, in which Orlando co-starred alongside Jennifer's then husband Brad Pitt.
However, it wasn't until October last year that they first made a connection while holidaying in Mexico at the One & Only Palmilla resort for the nuptials of their mutual manager, Aleen Keshishan.
Getting close: Orlando, joined by the Desperate Housewives star, is said to be harbouring a crush on Jennifer
Then, in February, they spent the night in close company while at a private party in the Hollywood Hills.
Jennifer and Orlando bonded over their shared devotion to yoga and spent the night playfully enjoying each other's company.
A source told Mail Online: "Jennifer is flattered by Orlando's attention."
"He has had a crush on her for the longest time. He loves her energy."
Fun lovers: the VIP guests were all smiles at the bash
Jennifer has been linked to a series of men in recent times, including her Travelling costar Aaron Eckhart, and is said to be taking her time choosing the perfect partner - and enjoying single life in the meantime.
After a weekend of play, it was back to work for Jennifer yesterday as she resumed filming her upcoming comedy Marley & Me in Miami.
Dressed in denim cut-off shorts and a casual tee, she was seen shooting scenes costar Owen Wilson, who plays a writer who adopts a mischievous dog.
Back to work: Jennifer Aniston was back filming scenes with Owen Wilson on set of Marley & Me in Miami yesterday
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