Though Holmes, 41, and Vitolo, 33, have only recently gone out in public together — first seen on September 1 in SoHo, New York, and most recently spotted at Peasant Restaurant in Manhattan on September 6 — their communication dates back to July 31, when Vitolo posted a comment to Holmes’ Instagram page.
Around the same time, however, Vitolo was tagged in an Instagram picture alongside the designer rumored to be his ex-fiancée on July 27 from the art page Bad Crystal Art. The portrait, with Emmons’ arm on Vitolo’s leg, was captioned: “date night is the best night.”
Emmons and Vitolo are tagged in numerous photos from earlier this year. On May 29, a drawing of Emmons and Vitolo kissing was posted by the account @issues_roses with the caption, “Any hardship in life can be cured by love”; and on February 21 a picture of Emmons, Vitolo and his dog, Lil Franky Vitolo, was posted by Bad Crystal Art with the caption, “Family portrait.”
According to In Touch, “Emilio and his fiancée Rachel Emmons broke off their engagement very recently.”
Emmons' Instagram account was recently made private.
Holmes, who was in a private relationship with Jamie Foxx for nearly six years, is no stranger to heartbreak. As OK! previously reported, the pair were “arguing nonstop over his partying” around the time of their breakup. At the time, a source said that Holmes was looking for a guy who was “mature and ready to settle down.”
Prior to Foxx, the actress was most famously married to actor Tom Cruise but filed for divorce in 2012 after five-and-a-half years of marriage. She was also engaged to actor Chris Klein in 2003 but never made it down the aisle.