Jay Cutler is keeping fans guessing when it comes to his relationship status. On Jan. 26, new photos surfaced of the 37-year-old lounging by the pool in Miami with a mystery woman. The pics were taken at the 1 Hotel in South beach on Jan. 20. Jay was shirtless and soaking up the sun while chatting up the gorgeous blonde, who was catching some rays in her bikini.
These photos were taken just two days before Jay and his ex, Kristin Cavallari, confused their fans by posting a photo together on Instagram. They both captioned the picture, “The world is full of users. 10 Years. Can’t break that.” Immediately, people began wondering if they had gotten back together after announcing their split in April 2020. Jay and Kristin were married in June 2013 and have three kids — Camden, 8, Jaxon, 6, and Saylor, 4 — together.
The exes didn’t specify what they were referencing in their Instagram captions. However, fans are convinced that it was their response to Southern Charm star, Madison LeCroy, allegedly talking about their relationship on Instagram Live on Jan. 21. Madison was briefly linked to Jay when he was spotted visiting her hometown in December. She was asked about the rumored relationship during an appearance on Watch What Happens Live with Andy Cohen on Jan. 7, but didn’t spill any juicy details. “I’m not kissing and telling, so…” she said.
Meanwhile, Madison’s ex, Austen Kroll, hung out with Kristin and her friends in December. They went on Instagram Live together and made headlines for the dancing videos they shared. At the time, fans wondered if Kristin and Austen were dating, but she shut down that speculation quickly by writing on social media, “I didn’t realize I wasn’t allowed to have FRIENDS who were guys.”
As HollywoodLife EXCLUSIVELY reported, Kristin and Jay’s friendly Instagram pic does not mean they’re back together. “Kristin and Jay will always have each other’s backs and that’s what posting that photo was all about,” our source explained. “They both consider themselves single right now. They’re working together as co-parents and support one another always.”
It’s unclear what happened between Kristin and comedian Jeff Dye, who she was spending quite a bit of time with in 2020. They were first spotted together when they were photographed making out at a bar in Chicago in mid-October. Although things were casual at first, they seemed to get pretty serious when the pair vacationed to Mexico together in early December. Photos from the trip showed them packing on the PDA while hitting the beach. However, the romance appears to have fizzled out since then.