The 26-year-old former Tottenham player began dating model Ruby Mae in 2016 but had a brief split in 2018 before they broke up for good in early 2021. In May of the same year, Alli was spotted kissing Maria Guardiola, daughter of Manchester City boss Pep. Although their relationship fizzled out by October, the former couple now appears to be on good terms.
Despite their previous affiliations with Alli, both Ruby and Maria get along well and are often seen commenting on each other’s Instagram posts. Last month, Maria posted a series of snaps from a dinner in Milan which received 75,000 likes and a comment from Ruby.
Maria visited Milan again last week, posting more pictures, to which Ruby responded with another comment.
Alli has since moved on from both Ruby and Maria and is currently dating model Cindy Kimberly. They began seeing each other last year, with Alli posting a gushing birthday message for her on Instagram that read: “Happy birthday mi amor. I love you.”
However, the footballer is currently enduring a difficult loan spell at Besiktas. He joined the Turkish side for a season from Everton last summer but has now been banished from the squad. During the international break, Alli appears to have returned to London and was spotted with Kim Kardashian’s son, Saint, who wore an Arsenal top despite Alli’s affiliation with Tottenham.
Alli stopped for a photo with the young fan, displaying good sportsmanship
