At Pops' house, Mordecai is brushing his teeth. Rigby and (Y/n) are standing at the door. "Look, you know I couldn't be happier that you didn't back down from going on this date with Anna. I admire that. But tonight we had plans! Man plans! Man's!" Rigby said. Mordecai turns to look at Rigby. "(Y/n)'s not a man." He said, and Rigby groans. "Come on! You know what I meant!" Rigby said. "I know, I know, but this is important. And I told you I was sorry. You still have (Y/n)." Mordecai said.

"Exactly! I can't just spend time with her tonight it will make things awkward!" Rigby protested, and Mordecai rolls his eyes. "Dude, come on, you're overreacting." He said. "Am I? If it's just me and (Y/n) eating pizza and prank calling Benson it's gonna feel like a date." Rigby said. "But we do this every Saturday; I'm only missing it once." Mordecai said, and Rigby points at Mordecai.

"You know this is a three best friend job." He said. But Mordecai wasn't listening, and goes back to brushing his teeth. "I'm not hanging out with you two tonight, dude." He said. "Uuuuuuuuuuuuugh!" Rigby dramatically throws his arms up and spins out of the bathroom. Later in the day, Anna is standing outside waiting for Mordecai. Mordecai opens the front door. "Hey!" She said.

"Hi, hey! So, um, I'm glad you could make it out tonight." He gives Anna a hug and she chuckles. "Woah! You're a real move maker today." She said. "Oh, uh... I mean... I thought..." Mordecai said. "Hey, hey, I'm just teasing! It's cool. You already got me on a date, there's no need to impress me." Anna said. Mordecai blushes. "Ha, yeah, it's cool. I'm cool." He said. "Pfft. Alright, cool guy. What are we doing on this hot date?" Anna asked. "Well, we could go eat at the new falafel fusion truck, or there's the tried-and-true Wing Kingdom,

and then after that I was thinking we could," Mordecai begins to count off on his fingers. 'Go catch a movie, or go to trivia night at the arcade, or take a chance on disco night down at that weird bingo hall." He said. "Yeah, sounds good." Anna said. "Uh... which one?" Mordecai asked. "All of 'em. Let's just start at the beginning and see how far we get." Anna said. "Okay."

They begin to walk away when all of a sudden, a ghostly green light appears, along with a portal that has spirits flying out of it. A van drives out of the portal, revealing Death and his wife, who appears to be yelling at him about something. Death then appears to be trying to reason with her. "Uh..." Anna points. "That van just came out of thin air." She said. "We should go." Mordecai tries to quickly walk off with her. "Do you know them?" Anna asked, still pointing. "Nope." He replied. "Hold it right there!"

A door is heard opening, and Death walks over to Mordecai and Anna before they can get away. Mordecai waves. "Ha ha. Hey, Death. How's it going?" He asked nervously. Anna looks at Mordecai. "Uh... Death?" She asked. Mordecai motions to Death. "Anna, this is Death." He motions to Anna. "Death, Anna." Death takes a close look at her. "Another chipmunk? Does she know your friend by any chance?" Death asked. "(Y/n)? Yeah, she's her sister." Mordecai said.

"You know my sister?" Anna asked Death curiously. "Of course I know her, been trying to get her soul for a while now." Death said. "Wait, what?" Anna asked, her eyes widen slightly. "Yeah, what?" Mordecai asked suspiciously. "Never mind." Death said quickly. "Well, it's been great running into you." Mordecai tries to leave again. "Oh, we're not through yet." Death gestures over to his van. "You're gonna babysit Thomas tonight." He uses magic to open one of the van's doors. Thomas is seen sitting in his baby seat with a grumpy expression on his face. "Aw, man!" Mordecai said.

Anna puts up her paws in defense. "Um, actually, we were just about to head out ourselves." She said. "Well, you're in for a change of plans, missy, because," Death points at Mordecai. "This joker owes me a favor." He said. Mordecai quickly glances over at Anna before coming up with a plan. "Hold on a second." He walks a few feet away and dials somebody's number. (Y/n) is heard answering the phone. "Yeah?" She asked. "(Y/n), I need you to do me a huge favor and babysit Thomas tonight."

Mordecai said. "Thomas is in college. I don't think he needs babysitting."  (Y/n) said. "Not that Thomas! Although, I'm pretty sure that Thomas would love to have you babysit him." Mordecai smirked. "Oh shut up." (Y/n) snapped. "But no, Death's Thomas! Can you help me out?" Mordecai asked.

"Sorry to hear that, but I've got some important plans that I can't cancel on!" (Y/n) said. Just then, her other sister Olivia walks over to her. "Sorry, we have to watch it on my computer." She sits down on the couch beside Rigby. "I haven't had a T.V. since I moved out of my old place." She said. Mordecai appears to be shocked. "Wait, are you and (Y/n) at Olivia's?" He asked. (Y/n) suddenly shouts back at him over the phone.

"VERY IMPORTANT!!" Mordecai cringes and lowers the phone. He groans in annoyance and then proceeds to walks back over to Anna and Death. "Sorry, Anna. Looks like I can't get out of this." He said. "We don't have to give up on our date just because of Thomas." Anna said. "Really?" Mordecai asked. "Yeah! I'll just help you babysit him. I'm sure we can still have a good time." Anna said.

"Okay. Let's do it!" Mordecai said. Death walks back over with Thomas in his arms. "Glad to hear it. We'll pick him up at eight." He suddenly remembers something. "Oh, a little heads up." He whispers to Mordecai. "Thomas is going through a little bit of a phase right now." He said. "Wait, what?" Mordecai asked. "Ciao!" Death walks back over to his van and drives away, disappearing through another portal. "So. We meet again." Thomas said. "Woah, he can talk?" Anna asked. "Obviously." Thomas said. Mordecai puts Thomas down on the ground. "Yeah, he's actually three hundred years old." He said. "Then why is he so shrimpy?" Anna asked.

Thomas gestures angrily at Anna. "Who is this female?" He asked. Mordecai points at Thomas. "Her name's Anna, and you're messing with our date plans, so try to be nice, okay?" He asked. "Date?" Thomas repeated. "Uh, yeah." Mordecai said. "And she's actually okay with being a girlfriend to someone like you?" Thomas asked. Mordecai blushes and rubs the back of his neck.

"Well, she's not really my girlfriend yet." He said, Anna is blushing and smiling as well. "Uh, we're just on a date right now-" Mordecai said. "Gah! Such simple minds! You mortals have the most tedious rituals." Thomas said, interrupting. "Hey, at least we're not three hundred and still wearing baby clothes." Anna fired back. "What?! How dare you." His eyes begin to flash a bright red color. This stops as soon as Mordecai addresses him, however.

"So, Thomas, what do you want to do?" He asked. Thomas points at him. "Take me to the playground!" He demanded. "Hey, not a bad idea. This could be pretty fun." Anna said. "Oh, we'll see about that." Little kids are having fun on a playground. A young boy goes down a slide and lands flat on his face in the sand below. "Where have you taken me?" Thomas asked. "It's a playground, dude." Anna said. "Yeah, go run around or something."  Mordecai said. "But where's the fire? The brimstone? The overall loss of hope?" Thomas asked.

There's a depressed man sitting on a park bench. "I don't know. That guy on the bench looks kind of sad." Mordecai said. Thomas crosses his arms. "Take me to the underworld playground." A stout, little kid walks over to Thomas. Thomas pushes him over, and the kid falls on his back, his arms and legs twitching. "You haven't tried it out yet. Give it a chance!" Anna said. "Come on, I'll push you on the swings."

They begin to walk towards the playground, the little boy's limbs still twitching in the background. Thomas complains loudly. "Daaaah! Gaaaaaaah!" Thomas gets pushed back and forth on a swing. He looks grumpier than before. "This is terrible! The swings in the underworld go much higher!" Mordecai continues to push Thomas, despite this remark. "Well, too bad." He turns when he hears music coming from an ice cream truck. The ice cream man is shown giving a little kid some ice cream. "Follow my lead." He whispers to Anna, who giggles. "Okay." She said. "Alright. I'm gonna push you really high this time!"

He pushes Thomas with all his might. "Now that's a good swing! Keep this up and I'll..." He realizes Mordecai and Anna are gone. "Wait. What the...?" Mordecai and Anna just received a cone of vanilla ice cream from the ice cream man. Mordecai holds the cone out to Anna. "Wanna share?" He asked. "Yeah, sure." They both go to hold onto the cone, causing their hands to touch. They smile at each other before being rudely interrupted by Thomas.

"Fools! You can't leave me alone! You are here to do my bidding! Now take me to the underworld playground." Mordecai and Anna look at each other. "We can't. Just play on this playground." Mordecai said. All of a sudden, Thomas lets out a cry of frustration. His eyes begin to glow red again, causing the big ice cream cone decoy on top of the ice cream truck to explode.

The ice cream man runs for cover. Mordecai yells in surprise as the ice cream cone he bought for him and Anna melts all over his hand. "Underworld. Underworld!" Thomas chanted. Mordecai's screams are heard over Thomas. "I'd take you but I don't even know how to get there!" He shouted. Thomas immediately stops throwing his tantrum and smiles. "I know how." Later the trio are being dropped off at Death's house via taxi. They are then shown in Death's garage as Thomas flicks on the light and presents something to Mordecai and Anna.

"This is how." Thomas said. "Dude, we can't all fit on that bike." Mordecai said. "Not that bike." Thomas points to another bike with a side car. "That bike." He said. "Great, but I still don't know how to ride a motorcycle." Mordecai said. Anna turns to Mordecai. "I have a motorcycle license." She said. "Then it's decided. The female you're trying to impress will drive us. How emasculating." Thomas said. Anna then proceeds to put on a biker jacket. Mordecai puts a helmet on

Thomas's head, which makes him frown in protest. They are all then seen sitting on the motorcycle, Mordecai and Thomas are in the side car and Anna on the motorcycle itself. She revs it up and begins to drive off. "It's pretty cool you know how to ride a motorcycle." Mordecai said. "Yeah, I did motocross when I was younger." Anna said. "Enough! Take a left up ahead and go into seventh gear." Thomas said. "seventh gear?" Anna asked. "DO IT!" Thomas shouted. "Okay, okay." She puts the motorcycle into seventh gear. The green headlights come on, which ironically are in place of a skull's eye sockets. A portal appears in front of them, and Anna screams in terror.

They are immediately transported to the underworld playground. "You get used to it." Mordecai said. "Ah." Thomas takes his helmet off. "At last!" They are at a playground that is surrounded by fire. It then pans around to show three evil looking spring toy animals and a sandbox with an eel-like monster it. The eel-like monster proceeds to eat a crow. Anna shudders. "Ughhh. This playground doesn't look very safe." She said. Mordecai  points.

"You wanna go sit down on those swings? I don't think they'll incinerate us." He said. Anna shrugs. "Sure." They walk over to a set of swings, which are composed of wood and bones for handles. Mordecai appears to be slightly disgusted. Anna doesn't really seem to mind, however, and sits down before Mordecai does. "Wow. Look at him go." Anna said. "Yeah. He's really in his element." Mordecai said.

Thomas feeds the eel monster another crow. Anna starts to swing back and forth, while Mordecai sighs and awkwardly climbs up onto his swing, making Anna giggle. "Hey, thanks for coming along and helping me. I don't know a lot of people who'd do that." Mordecai said. "Well, it's no disco night at the bingo hall, but I'm having a lot of fun hanging out with you." Anna said. "Really?" He sits down on his swing, and Anna bumps into him playfully. "Yeah, really." They both start to laugh. Anna grabs onto one of his swing's handles, pulling him closer.

"You know, I think this date is going pretty good." She smiles at Mordecai, and he smiles back. They lean in to kiss each other, when suddenly, Thomas appears out of nowhere. Mordecai screams in surprise. "Push me!" Thomas said. "Uh, yeah." Mordecai gets out of his swing. "Here you go." He said. "Don't patronize me. These are baby swings. I wish to go on the elder boy swings."

A much scarier set of swings is shown, complete with skulls, spiky poles holding them up, and a cauldron of fire at the top. Mordecai gulps. "Sure." He begins to walk away with Thomas. "I'll meet you guys there. I gotta hit the restroom. I'll scream if I need you." Anna said. "Got it." Mordecai and Thomas continue to walk over to the elder boy swings, where a praying mantis lady is now pushing her child. Thomas chuckles at something, and Mordecai suddenly grows suspicious.

"What's so funny?" He asked. "Hmmph. You and that female babysitter are never going to connect." Thomas said. "What are you talking about?" Mordecai asked. "Oh, it's been so easy to get between you all day. What a pitiful romance. I've barely been able to keep a straight face." Thomas said. "What the... you've been trying to get between us?!" Mordecai asked. "Trying?" Thomas laughs. "It's been as effortless as it's been entertaining." Thomas said.

"Ugh. You little jerk." Mordecai points at Thomas. "That's it, we're going home." He said. "Oh, we'll see about that." He begins to shout so that the praying mantis lady can hear him, as well as anyone else who might be on the playground. "What? No! I will not ask this woman for her phone number!" Thomas said. "Huh?" Mordecai asked. The praying mantis lady looks over at them. "She's obviously married! I can't believe you're asking me to pick up women for you while your date is in the bathroom!" A Cerberus mother sits on a bench, reading a book while her child plays with a toy truck. She looks up in disgust.

"Did you hear that? How awful!" A serpent's child is sitting beside him. "Ugh. Who would do such a thing?" Anna walks back over to Mordecai and Thomas, unaware of what is happening. "Hey you guys, what's going on here?" She asked. Mordecai laughs nervously. "Not much. We should probably get out of here." Before they can do that, a shadow looms over Mordecai.

"Hey, buddy!" Mordecai turns around. A Minotaur is wearing a rather angry expression. "Are you trying to pick up my wife? Well?" He asked. Mordecai waves his hands frantically. "No, no! I'm just the babysitter!" He shouted. "What kind of sicko uses a child to try to pick up a married woman?" The praying mantis lady responds to him in some weird form of insect gibberish. "Look, it's not really like that. I'd never go after your wife, honest!" Mordecai said.

"Oh? So now my wife isn't good enough? You think she's revolting just because she's pregnant with hundruplets?! " The Cerberus mom begins to walk over, growling menacingly. "We need to get out of here!" Anna shouted. The Minotaur begins to roar as well. Mordecai grabs Thomas and takes Anna's hand. "Come on!" They leap onto one of the elder boy swings, swinging over a seemingly bottomless abyss that lies below. They land roughly and begin sliding on the ground.

They quickly get up and run away as the playground monsters pursue them. "We've got to get to the bike!" Anna shouted. One of the spring toys narrowly misses hitting Anna. The Minotaur is then shown throwing another one, which lands right in front of them and causes them to be blown back. Mordecai looks up worriedly as they hit the ground. "Anna!" Mordecai shouted.

Anna grabs her leg, which appears to be hurt from the fall. Mordecai quickly runs over to her with Thomas as the third and final spring toy is thrown at them. He helps her up, and they run over to the motorcycle. "Wait!" Mordecai looks up as he puts Thomas in the side car. "I can't drive! My ankle is messed up." Anna said. "Uh, okay. Then get in the side car!" She hops into the side car with Thomas. Thomas puts on a helmet and she does the same. Mordecai puts one on as well and gets on the motorcycle.

"Tell me how to start it!" The serpent father roars and throws a sharp boulder at them. They cover their faces as debris scatters everywhere. "Uh... turn the key!" He turns the key. Mordecai quickly pulls out and almost drives right into a boulder. The playground monsters quickly chase after them in hot pursuit. Mordecai swerves and catches a glimpse of the monsters behind him.

"We're not going fast enough!" Mordecai shouted. "Get out of first gear! " Mordecai tries to do what she says, but he only ends up stalling the motorcycle instead. "Huh?" They get yanked back towards the monsters. "You stalled it! Turn it back on!" Anna shouted. "I thought you said this was easy." Mordecai said. Anna puts a hand to her head. "Ugh, I was just trying to look cool!" She shouted. Mordecai revs the motorcycle and smiles as it starts back up. He continues to drive forward as the monsters follow close behind. "Can't this thing go any faster?" Thomas asked.

"This is all your fault! You make it go faster!" Mordecai shouted. "I know a way to go faster." Anna said. "Really?" Mordecai asked. "Yeah, we just need to get rid of some dead weight." Ana said. The monsters are seen behind them again. "Well then, hurry up!" Thomas shouted. "My pleasure!" She holds Thomas over the edge of the side car, acting like she's going to drop him.

"What? No!" Thomas frantically kicks his fee. "Stop this at once!" He shouted. "Oh, yeah? Why should I? This whole time you've been trying to get between me and Mordecai." Anna said. "No! No I... t-that doesn't sound like me!" Thomas shouted. "Yeah, right. You told me so yourself!" Mordecai shouted. "I've been looking forward to this date for a long time, and I'm sick of you messing it up!" Anna shouted. Mordecai looks over in awe and smiles. "Well, out you go!" Anna said. "No! Pull me in!" Thomas flails his arms and legs. "PULL ME IN!" He screams.

The force of his screams causes a miniature abyss to open up in front of the monsters. A boulder falls in, causing molten lava to splash up and cover the serpent. The Cerberus and praying mantis lady are caught off guard and ram right into a boulder. The Minotaur is the only one remaining. Mordecai manages to hop over a chasm and get himself, Thomas, and Anna to safety. The Minotaur snorts and tries to make the jump as well, but only manages to fall to his death in the chasm.

"No! I'm the victim here! You're the one who hit on my wife! I was just playing with my kids!" He finally hits the bottom of the chasm. Thomas opens his eyes when he realizes that they are no longer in danger. "Huh?" He asked. "We totally tricked Thomas into thinking we were gonna drop him!"

Mordecai and Anna do a trademark 'OOOOH!' and high five. "Let's get out of here." Mordecai shifts into seventh gear, and another portal appears in front of them. "Being tricked is one of my least favorite things!" Thomas begins to throw a tantrum inside the portal, causing the motorcycle to spin and turn upside down. They exit the portal and Mordecai swerves, crashing through Death's garage door. They all land on the ground.

Thomas groans and picks himself up, taking off his helmet in the process. He then begins to laugh. "When I tell my daddy what you've done, he'll torture your souls for all eternity! Good luck going on your dates then!" He laughs and bangs on the wall, causing a bowling ball to roll down towards him. "Uh..." Anna said, but Mordecai silences her. "Shhh.... Shh... Shhh... " The bowling ball falls and hits Thomas right on the head, knocking him out. All of a sudden, a door is heard opening, and Death walks in. "What the... " Thomas is now on the ground, snoring softly. Mordecai and Anna quickly stand up. "So, looks like you're two for two, Mordo.

If you don't watch yourself, I'll have to enlist you as a full-time sitter." Death laughs. "Ha ha..." Mordecai said nervously. Death pokes a finger in Mordecai's chest. "Now get out of my garage!" He walks away with Thomas and slams a door that leads to his house. "Wait, you don't get paid?" Anna asked. "Nah, he just lets us live." Mordecai said. "Well, really I should thank you for that. I can't believe you learned how to ride a bike so fast; that was awesome!" Anna said.

"Yeah, well, I was just trying to look cool." Mordecai said. Anna playfully shoves him. "Alright, alright, I can get wanting to impress your date." She said. "So did it work?" Mordecai asked. "He doesn't need to impress me, I already think he's cool." Anna said. "Well, he thinks the same about her. You've really been looking forward to this for a long time?" Mordecai asked. "Yeah." They share their first intentional kiss. "Want a lift while we try to hail a cab?" Mordecai asked. "Oh, please!" Anna said. Mordecai lets Anna hop onto his shoulders, and he carries her away while they share a good laugh.