Things seemed to have cooled between the pair recently with the 61-year-old Kardashian matriarch being linked to a Nigerian businessman Christopher Cunningham recently.
But both Jenner and Gamble, 36, were all smiles as they left celebrity hotspot Craig's in West Hollywood on Saturday evening.
Kris, 63, wore a colorful a floral style robe while her much younger guy dressed in a casual blue shirt with matching pants for their rare public appearance.
As the pair left the popular restaurant they were joined by famous clothing designer, Tommy Hilfiger.
Maybe, a new deal is in the works for the Kardashians to wear some of his trendy outfits on one of their shows.
Whatever the reason, Kris was certainly all smiles as she walked with her handsome friends back to her waiting SUV.
This has been a busy time for her with both her daughters, Khloe and Kylie, both currently expecting babies amid reports she recently splashed out $1.65 millon on a new Calabasas condo to be closer to them.
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