Jay Cutler and Samantha Robertson ​Are Getting ‘Pretty Serious’ Together: Inside Their Romance!

Jay Cutler and Samantha Robertson have made their relationship Instagram official! “Sunsets in Montana never disappoint,” she captioned a September 25 pic of her and the former NFL star, 40. “Jay and Samantha have been close friends for years,” says a source, who notes Jay was pals with Samantha’s ex-husband, Trace Ayala, and she was friendly with his ex-wife, Kristin Cavallari. “Their families hung out and even vacationed together.” Now that they’re both single, Jay and Samantha, 33, “are giving things a shot,” a source exclusively tells Life & Style. “It’s only been a few months, but they’re already pretty serious.”