Ripe for the Picking

Both series show the personal growth of two virgin protagonists seeking to lose their virginity and then finding love along the way.

While the female protagonists couldn't be more opposite Uri wo Waru's being a virgin, Raise de wa's being a self-proclaimed 'slut' both series focus on mature relationships. The focus is less on will these two get together, but on previous established relationships. The casts are working class adults navigating not only romantic and or sexual relationships, many of which are considered atypical in Japan. There's also subplots regarding exploration of sexual orientation as well.

A slightly similar premise with a work related romance. There is an age gap between the male and female leads, where both women are the older ones. Also, there is a fair amount of skinship in the two dramas.