Football star Dele Alli was recently seen enjoying a sunny day out in Milan alongside a mystery brunette — just weeks after his high-profile split from longtime girlfriend Cindy Kimberly.
The 29-year-old midfielder, now playing for Italian Serie B side Como, looked relaxed as he strolled through the fashion capital dressed in a light blue Nike tracksuit, visiting luxury stores like Goyardand Loro Piana. He was accompanied by a few friends and the unidentified woman, who wore beige shorts, a white blouse, and dark sunglasses — drawing attention for her striking resemblance to Cindy.
⸻
A Swift Move On?
Their outing comes hot on the heels of Dele’s confirmed breakup with model and influencer Cindy Kimberly, 26, after more than three years together. Fans first noticed signs of trouble when Cindy deleted several photos of the pair from her Instagram. She later confirmed to GSM:
“We’ve been separate for a little while already.”
While Dele was spotted in Milan, Cindy was seen vacationing in St. Tropez with her friend Chantel Jeffries, soaking up the sun following the split.
⸻
A Relationship Once Full of Promise
Dele and Cindy had first gone public with their relationship in 2022, while he was still playing for Everton. Their bond appeared strong, especially after Dele moved to Italy in January to join Como in an effort to revive his faltering career — a move Cindy supported by relocating with him to northern Italy.
She had stood by him during one of the darkest periods of his life. In a deeply emotional interview with Gary Neville last year, Dele revealed his traumatic childhood, including sexual abuse at age six, and battles with addiction and mental health. Cindy was widely seen as a supportive and grounding presence throughout that time.
⸻
Rocky Start at Como
While the former Spurs and England midfielder had hoped for a fresh start in Italy, his return to football hasn’t gone smoothly. His debut appearance for Como against AC Milan ended in disaster — Dele was shown a red card just 10 minutes in for a reckless tackle on Ruben Loftus-Cheek.
His manager, Cesc Fàbregas, didn’t hold back post-match:
“It is a grave mistake… a player of his experience should not make such an error.”
⸻
New Chapter?
Though his football career remains uncertain, Dele appears to be finding comfort off the pitch. Whether the Milan outing marks a new romance or just a friendly outing remains to be seen — but one thing is clear: Dele is stepping into a new chapter, both personally and professionally.
ent360news | For the stories beyond the headlines
