Following a one - night stand in 2014 , Oscar and Maddy began a relationship the following year , as he supported her through a cancer diagnosis .
Oscar 's first love interest was his friend Maddy Osborne ( Kassandra Clementi ) .
Following a one - night stand in 2014 , Oscar and Maddy Osborne began a relationship the following year , as Oscar supported friend through a cancer diagnosis .
Oscar 's first love interest was his friend Maddy Osborne ( Kassandra Clementi ) .