As RadarOnline.com's photos show, the Kardashian family momager, 63, and much younger beau, 38, strolled through the gorgeous fishing village and holiday resort on the Italian Riviera.
However, they didn't interact much and their body language appeared cold.
Kris and Corey met in August 2014 at fashion designer Riccardo Tisci's 40th birthday party and started dating.
In 2017, Radar learned that the couple had taken a break so Kris could “focus on her family and the show,” a source said. Later that year, she was spotted flirting with music producer David Foster and was even linked to Nigerian billionaire Christopher Cunningham.
Then Kris and Corey rekindled, but as Radar exclusively reported, there was tension in their relationship because she repeatedly rejected his marriage proposals, an insider noted.
Now, they are barely smiling while on an outing in romantic Italy on Sunday, July 7.
Kris was all covered up in a big black summer dress that looked like a tent, while Corey wore a casual white shirt and black pants.
PDA was sadly missing from the scene!
Scroll through Radar's gallery for more on their depressing holiday.
Taking A Walk
Kris and Corey walked alongside each other but appeared lost in their own thoughts while on holiday.
The two seemed to keep distance between them.
Kris didn't smile during most of the time she was with her boyfriend this weekend.
Not Smooth Sailing
The mother of the famed Kardashian/Jenner clan appeared downcast even while sitting on a boat in Italy.
All Dressed Up
Kris kept her body under wraps in a black dress and wore a hat and sunglasses, plus lots of jewelry on the trip.
Trouble In Paradise?
Hunky Corey has been Kris' constant companion for years, but this weekend, he appeared not to be pleasing the Keeping Up with the Kardashians star.
Always By Her Side
Kris has brought Corey as her date to numerous red carpet events, including the MS Gala in May.
Is Kris and Corey's romance the real deal? Fans wondered after he started appearing on KUWTK, giving Kris some sexy storylines.
Relationship Under Fire
In 2017, a PEOPLE source claimed that "Kris is basically Corey's sugar mama," and the "relationship is more business than romantic."
No Stepdad Figure
Corey told Kris' children on a KUWTK episode, "I’m a young dude dating your mom. Y’all are not really my f***ing kids. We are technically peers."
Corey always looks handsome and he's accompanied Kris to such big celebrity events as the MET gala.
No More Marriages?
In 2018, Kris opined that after two failed marriages, to the late Robert Kardashian and Bruce, now Caitlyn, Jenner, she probably won't walk down the aisle again. Sorry, Corey!
"I'm in a great relationship right now," Kris has previously said about her young boyfriend.
Will It End?
Corey hugged Kris at her 63rd birthday party last fall, but now, things look tense.