Now George Clooney has introduced his current squeeze Stacy Keibler to former flame Karen Duffy as the trio took a boat ride on Lake Como today.
Duffy and the Hollywood heartthrob dated briefly in 1995 and still remain very good friends.
Cosy trio: Stacy Keibler got to know George Clooney's former flame Karen Duffy as she they went for a boat ride on Lake Como, Italy today
She said of Canalis to People magazine back in 2010: 'The woman he's with now is incredible – she's funny, smart, has lovely manners. She's exactly who you'd want one of your friends to date - she's just as beautiful on the inside. And George – you know ... he's very loyal.'
Moving onto Stacy, and it seems that Duffy is equally happy with George's new girl as the two women seemed to be getting along famously during the sun-filled day out.
Comparing notes? The duo enjoyed an intimate chat on board of the boat, while George was busy socialising with other friends
New friends: The two women seemed to be getting along famously during the sun-filled day out
Stacy was seen gallivanting in New York only three days ago after her first Italian getaway with boyfriend George.
But it seems she couldn't pry herself away from her leading man longer than a few days.
The couple were reunited at the movie star's villa on Lake Como, at the weekend, and joined their friends for a relaxing cruise along the coast today.
Reunited: Stacy and George were reunited after she jetted back to Italy over the weekend
She topped her look with a cream and black fedora and was seen boarding a boat with Clooney, ever the gentleman, helping her on board.
The actor was dressed down in a blue button down and matching shorts for a monochromatic look.
The Oceans 11 star took the helm, and the couple, joined by a small group of friends including model/actress Karen Duffy, sped off onto Lake Como.
Helping hand: The 51-year-old actor unloads the boat as the group heads to their next adventure
Going strong: Stacy, 32, and George, 51, have been dating 11 months
But her trip to New York proved to be a short one, although the 32-year-old retired professional wrestler still managed to turn heads on her brief trip to the Big Apple.
Wearing suede ankle boots and a simple cotton T-shirt tucked into her paisley denim shorts, Stacy on Friday strut through Manhattan's fashionable SoHo district on a shopping trip.
Relaxed: George flashed a smile before boarding the boat
But by Sunday, Stacy was back on the Italian coast.
She took to her Twitter account during the Europ Cup, writing: 'Nothing better then being in Italy cheering them on in the #eurocup !!! Go ITALY!!!!'
At the helm: George navigated to the group's next location
Of course, Spain would go on to win the European Chamionship final, beating Italy 4-0.
Still, life indeed seems full of sunshine and sand for the blonde beauty, who kicked off her first trip to Lake Como with 51-year-old George just a few days after they vacationed in Cabo San Lucas.
In the 11 months they've been dating, she has already joined Clooney in Cabo five times.
And we're off! The couple seems to be avoiding the holiday rush for America's Independence Day by spending it soaking up sun in Lake Como