Note: The order of events has been subtly confirmed by PhantomArcade. Additionally, it can be concluded that the canon events of the original games/animations of guest characters have occurred, unless stated otherwise.
Pre-Tutorial
- Some time prior to the events of the game, Daddy Dearest seals a person away inside of Girlfriend's favorite dating simulator. This person would become the entity known as "Spirit". Who he was or his relation to Daddy Dearest is unknown. Many other people who have crossed Daddy Dearest are implied to have suffered similar fates.
- Daddy Dearest retires from being a rockstar.
- Boyfriend and Pico are a couple in Pico's School: Love Conquers All, but they break up shortly after the events of Pico's School. Years later, Boyfriend drops out of college to follow his dream of becoming a famous rapper and later meets Girlfriend. After winning her heart over with fingerboard tricks, they're ready to hit it off.
Tutorial and Week 1: Daddy Dearest
Boyfriend wants to date Girlfriend, but her family does not welcome him. After a warm up session with Girlfriend, he has a sing-off with her father, Daddy Dearest, to decide whether or not he is worthy to date her. Boyfriend wins the battle, but Daddy Dearest still keeps a close eye on him.Week 3: Pico
Unwilling to accept defeat, Daddy Dearest hires a hitman, Pico, to kill Boyfriend. However, Pico was only given a location and not a name. He reaches the Newgrounds office building, where he sees Boyfriend and realizes he was the target. Instead of killing him, Pico decides to spare him, but not before having a rap battle, to which Boyfriend wins.Week 4: Mommy Must Murder
Boyfriend has a dangerous sing-off with Girlfriend's mother, Mommy Mearest, while on top of moving limousines surrounded by Henchmen who act as backup dancers. With Boyfriend emerging victorious, he is begrudgingly "accepted" into the family.Week 2: Spooky Month
Note: Week 2 canonically takes place after Week 4.On Halloween night, Boyfriend is invited to Girlfriend's family home to give out candy to trick-or-treaters. Skid and Pump were passing by the house when Monster approaches them and convinces them to retrieve Girlfriend. The kids soon challenge Boyfriend to a rap battle for Girlfriend as their "treat" if they win. Boyfriend wins the battle, but after they leave, Monster challenges Boyfriend, threatening his and Girlfriend's lives due to his plans of eating Girlfriend. Monster ultimately loses, and the couple lives.
Week 5: Red Snow
During the holiday season, while on a nighttime trip to the mall, Girlfriend's parents take the Mall Santa working there hostage in order to have a rematch with Boyfriend in front of the mallgoers. However, Monster crashes the sing-off and uses his demonic abilities to warp the setting, making it darker; the mall is soon abandoned, except for Boyfriend and Girlfriend. He challenges Boyfriend once more, but he is beaten once again, sparing the couple.Week 6: Hating Simulator ft. Moawling
Boyfriend and Girlfriend are playing video games in her room when she pulls out an old anime dating sim that she used to play prior to dating Boyfriend. While they are playing it, Daddy Dearest sneaks up behind the couple and throws them into the game. Inside the game, Boyfriend is quickly challenged to a duet by Senpai, the game's main character and love interest. As Senpai loses to Boyfriend, he breaks down due to not being able to win over Girlfriend, far too used to being loved and winning. With Senpai at his most vulnerable, he is brutally killed when Spirit awakens. Spirit shows himself to be one of the many victims of Girlfriend's father. He challenges Boyfriend to a sing-off, hoping to steal both his and Girlfriend's bodies for himself to escape the game and take revenge. Boyfriend however, ends up winning and he and Girlfriend escape the game, leaving Spirit behind.Week 7: Tankman
Note: Week 7 canonically takes place after Week 8.In another attempt to kill Boyfriend, Daddy Dearest and Mommy Mearest cause an airplane he and Girlfriend are on to crash. After surviving this, the two find themselves in a restricted battlefield where Tankman and his army hold them both captive. Since their day was going so slow, Tankman decides to challenge Boyfriend to a sing-off instead of killing them on the spot. After being humiliated in battle twice, Tankman orders his men to open fire on Girlfriend. Just as she is about to unleash her demonic powers, Pico, who was sent by the parents to confirm Boyfriend's death, arrives on the battlefield in time to shoot down Tankman's army. Boyfriend, now with Girlfriend at his side, and Pico assisting the couple by single-handedly fending off the Tankmen, is challenged by Tankman one final time. He is ultimately defeated and the trio survives.
