Five Dates is a British comedy drama series created by Tiger Starr and Jonathan Cooper, and is the first app version of the series. The series stars Vinny Dawson, a millennial man, who is forced to video date with five women after losing his job.

Vinny is a shy and awkward young man who is trying to navigate the world of online dating. He must face his fears of getting rejected and not knowing what to say or how to act.

In the series, five women approach Vinny and ask him to video date them. The women are very different from each other, and the first impression that Vinny has of each of them is really the first impression that they will have of him.