The Lollipop hitmaker was spotted sitting next to Milian at the Nokia Theatre event in Los Angeles, which was hosted by his pal Drake.
Wayne also arrived at the prizegiving hand in hand with the Dip It Low singer, who he signed to his Young Money record label in 2012.
Milian recently ended her engagement to music mogul Jas Prince, and prior to their break-up, Wayne released a song called Tina Turn Up Needs a Tune Up, which fans believe is sly dig at Prince and a confession of his love to Milian.
The lyrics include, "I'll take your Tina (Christina)/She need a king, f**k them princes/You’re a queen/Let’s have a princess".
Incidentally, Wayne and Milian are both connected to music producer The-Dream - Wayne was previously engaged to The-Dream's first wife, R&B singer Nivea, while Milian was also married to The-Dream, but divorced him in 2011 after just a year of marriage.