Dinner guests in the UK were able to chat live with their Italian dates through a video call while they ate food delivered from Rossopomodoro, one of Deliveroo's oldest restaurant partners.
Deliveroo's head of brand experience, Jesse Boyce, said the event was designed to bring "people together" through technology and food.
A popular topic of conversation at the event was a recent news report about Brits being scared to eat spaghetti on dates, leading to the Italian diners offering some much needed lessons about how to the dish properly.
The "Milan Upon Thames" experience was booked out on both days it ran.
Boyce said Deliveroo is looking "to expand further" the project in different markets and countries.