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In its penultimate episode Choose-A-Rooney, Diggie confesses to Maddie that he had been regretting leaving Maddie when he was in Australia. We're never going to be able to enter the couples' contest now.
However she states that she is dating Josh and is very happy.
Finally, Maddie and Diggie get a chance to "talk" and as they were about to kiss, Joey almost interrupts them once again but fails thanks to Liv and Artie who realized what was about to happen just in time to shove him out of the way.
He performed Liv's song As Long As I Have You for Maddie which led to her and Josh breaking up. I got this really cool knight costume and it is going to melt your face off! Hey I'll go as that too then, maybe we could win the couples' costume contest? Diggie: Er, and you know when I mean couple I mean the contest category and... Later on when she talks with Liv, she admits that she still has feelings for Diggie but is torn between him and Josh. Liv is sure that Maddie still wants to be with Diggie after she sees them have fun at Gemma and Johnny Nimbus' wedding. They decide it is time to move on, but still stay good friends and possibly get back together when he is back and the time is right. In Co-Star-A-Rooney, Karen helps Maddie to overcome her feelings for Diggie with a "cleansing ceremony" by sending away all the stuff Diggie ever gave to her among her feelings.