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Diggie revealed he still had feelings for Maddie in Video-A-Rooney as he wanted to help make Liv's band make a music video with Parker, to spend more time with Maddie.It was then shown in the season 2 finale, that Diggie still had feelings for Maddie.So afterwards she gets him to say how he would introduce her if he were a sport's announcer.After he does, she smiles, glances at Maddie and says, "Um, approved." Liv is shown to be a Miggie shipper when she helps him out in getting Maddie back in Choose-A-Rooney.While Diggie is mostly embarrassed of his younger brother, due to his overbearing, egotistical, and geeky personality, and because of his weird hobbies. She thinks Artie is acting up because his role model Diggie is moving to other places like, Tundrabania and Australia. They used to appear to get along great and are very similar to one another.Diggie has made an attempt to ask Maddie out, but she miserably fails to flirt/respond back.
They started dating in Move-A-Rooney, but broke up in Flugelball-A-Rooney.
Digbert "Diggie" Smalls is a recurring character in the Disney Channel original series Liv and Maddie. He’s driven and loves basketball, but he has a soft side that he isn’t afraid to expose.
He was captain of the boys' basketball team and is currently in a relationship with Maddie. He’s funny and quirky, and he has a certain charming nature to him that we see when he gets nervous and playful around Maddie.
The premiere of the 3rd season Continued-A-Rooney continues the cliffhanger which showed Maddie rushing to the airport to see Diggie one last time to confess she still liked him but turned out Diggie had left already which leaves Maddie upset.
Although Diggie also comes back for her at her house and Maddie does not know about it.
In Sky Volt-A-Rooney, Diggie pays him back by ruining his kiss with Willow, but they still kiss anyway. In Switch-A-Rooney, Diggie tries to get Pete to like him so that he and Maddie can date.