Tutorial and Week 1: Daddy Dearest
Boyfriend wants to date Girlfriend, but her family does not welcome him. After some warm-up training with Girlfriend, Boyfriend has a sing-off with Daddy Dearest, Girlfriend's father, to decide whether or not he is worthy to date his love interest. Boyfriend emerges victorious, but it was made clear that Daddy Dearest will be keeping a close eye on them.
Week 3: Pico
Unaccepting of his loss, Daddy Dearest hires a mercenary, Pico, to kill Boyfriend. However, Pico is only given a location for his target which happens to be on the rooftop of the Newgrounds office building. Once Pico arrives at the specified destination, he recognizes Boyfriend and realizes he is his target. Instead of going through with the job, he decides to spare him, but not before having a rap battle.
Week 4: Mommy Must Murder
Boyfriend has a rather dangerous sing-off with Girlfriend’s mother, Mommy Mearest, on top of moving limousines surrounded by Henchmen that act as backup dancers. Boyfriend wins and with this victory, he is finally "accepted" into the family.
Week 2: Spooky Month
On Halloween night, Boyfriend is invited over to Girlfriend’s family home to give out candy to trick-or-treaters. Skid and Pump were passing by when Monster convinces them to retrieve Girlfriend for him. When the two arrive at the house, they challenge Boyfriend to a sing-off for Girlfriend as their "treat" if they win. Boyfriend wins the battle, but after the kids leave, Monster steps up to the challenge himself, threatening their lives due to Boyfriend's interference with his plans of devouring Girlfriend. However, he ultimately loses as well and the couple lives.
Week 5: Red Snow
During a nighttime trip to the mall around Christmas time, both Daddy Dearest and Mommy Mearest take the Mall Santa working there hostage to have another sing-off with Boyfriend in front of a large crowd. However, Monster later crashes the sing-off and uses his demonic abilities to twist everyone's perception, causing the mall to look abandoned (except for Boyfriend and Girlfriend), and make the once bright location suddenly become dark and gory. He challenges Boyfriend once more, but is beat once again, leaving the two with their lives.
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