Before we dive into the story, I wanted to take a moment to thank all of you guys who have stuck around and seem interested in my personal little Happy Tree world!

I worried for a while that Skippy would slowly come off as annoying for how much I post of her. Then when deciding to start her relationship with Pop I was worried it wouldn't be that well received since it's a fan character x canon. So, I was blown away when I saw just how much support I got from you all!

All the art, stories and sweet things you all have given have touched my heart immensely so really thank you all! I truly wish I could show just how much it all means to me ;u;.

Now as stated before there will be two stories posted. Their meeting then their confession!

So enjoy Y'all!

[Bonus: if you want to try reading this in the style of the show!)


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Happy Tree Friends

Bound to Say Hello!


Pop & Cub



Also Starring:





Feat. Skippy!

Almost There...

It all started one warm afternoon in the mid-months of summer. Happy Tree Town was livelier than it usually was as the residences were going about their day enjoying the heat on their shoulders. A particular bustle could be seen in the town's very own Petal Park which held most of the days' exciting activities. One such activity was one of Cuddles' very own baseball games.

Joining his team was his good friends Toothy, Lumpy, Russell, Flippy, and Flaky. Flippy as the umpire was chatting to Toothy giving him pointers on his next swing as the batter, while Cuddles held his placement proud as pitcher. He would tease Toothy playfully trying to show off to the little audience that sat waiting for the game to start. Amongst those watching was none other than Pop and Cub, the loving but ultimately broken bear family.

Cub was playing with Pop with a branch of leaves he found lying in the grass beside him. Pop chuckled full-heartedly at his son's antics and ruffled his fur till he heard the blow of the whistle signaling that the game was starting. He turned quickly to see the teams getting into position and started hooting in excitement. Cub followed in blind acknowledgment even as the child had no understanding of what was happening. All he knew was his dad was happy so that meant something good was happening!

Cub watched in awe as the first ball and swing made the other players move. For what reason he had no idea, but it was interesting to see. he watched alongside his father for a good few bats until eventually, he started to become bored of the paaainfully long pauses in between. They'd last for waaaay too long in Cub's young, impatient mind. So, we found his own fun with his leaf branch.

An airplane passed by in the distance giving Cub the idea to pretend the leaf branch was an airplane. He danced the branch back and forth giggling till he was upon his tiny feet and "flying" around in the grass. Pop focused on the game at hand, leaving Cub to wander farther and farther up the hill that leads to winding sidewalks that scattered the outline of the park.

Cub began to sprint down the first sidewalk he found with his branch high in the air above him, making whooshing noises as he did. Cub was completely transfixed on his pretend plane that he was unaware of a certain red-furred kangaroo mouse walking his way. The other tree friend also having no clue of Cubs nearing presence... that was until it was too late.


Pop watched as the ball soared from Toothy's tail and bounced from plate to plate as Russell ran home. Lumpy had the ball and was about to tag Toothy out but ultimately tripped forward over a rock lodged in the sandy grounds sending the ball straight at Pop. He gasped standing straight up with his paws outstretched trying to catch it, and to his delight he did!

He raised the ball with a hurrah of excitement paying little attention to the now devastated tree friends shocked over a now empty-headed Lumpy on the ground. Pop prided himself in his victory and turned to share his excitement with his son in his gibberish tone.

"Look, son! I caught it! I caught the-!" Pop paused. Where was Cub? He was right there sitting next to him mere seconds ago playing with his branch. He couldn't have run off... Could he?

Oh no.

Pop dropped the ball and took off in sheer panic in search of Cub. His son could be in trouble! He could be hurt! Oh, why didn't he turn around sooner! He searched the grassy grounds for any signs of Cub's whereabouts till he saw a leaf trail leading up to the sidewalks up the hill. That has got to be from his son's branch, it just had too! So, he took off up the small hill and followed the leaves down the walkway pushing through ongoing Tree friends passing by.

"Cub! Cub where are you?!" Pop called but with no answer.

He kept running till he saw the sidewalk curve past some high grown bushes littered with red roses. The thought of Cub pricking his soft tiny paws terrified Pop to no end as he swung around the bush in preparation of seeing something tragic, but to his surprise that's not at all what he saw. Instead of seeing his son surrounded by his blood, he saw his boy giggling as a tree friend he didn't recognize danced Cub's small branch around in the air while singing a silly tune.

He sighed with relief overseeing that his son was safe and slowly made his way over to the two. Cub was going to have a firm talking to once they made it home. Pop approached the two and cleared his throat, hoping to catch their attention. The stranger looked up in surprise while Cub hoped to his feet and ran to Pop in happy glee.

"Daddy! She makes the airpwane fly with music dad-dy! Come see!" Cub babbled as he pulled at Pop's right paw towards the strange mouse in front of them. The said mouse stood back up with a small friendly smile on her face.

"Oh, is this little cutie yours?"

"Uh heh oh yes he is haha. I greatly apologize for any trouble he may have caused," Pop apologized

"Oh no, he was no trouble at all. If anything, it was my fault. I wasn't paying any attention to where I was going and the poor guy ran straight into me! I felt absolutely terrible so I attempted to cheer him up! I think the bump-in scared him more than anything but I did check to see if he was hurt. So, if anything, I should be the one to apologize," The mouse said with her hand on her chest. She crouched down to Cub's height once more.

"Now you stay with your father, sweetheart. He loves you very much and wouldn't want to see you get hurt. So, no more running off alone, okay?" She smiled and handed Cub his branch back. Now only a single red leaf hung to it near the very tip. Cub giggled and took the branch happily before babbling a toddlers thank you to her. She smiled back then stood back up once more.

"Well if you won't take my apology, at least have my thanks for making sure he was ok. I don't know what I would have done if I lost him (again). I shouldn't have let him wander off like that..." Pop said while patting the top of Cubs head protectively. The lady mouse softened some before replying.

"Parenting can be difficult at times. Children are curious and want to play with the world around them. So, at times they may slip away to find out what that shiny thing is over the fence. Don't fault yourself for their curiosity, just be there ready for when they try again," And with that, she began to walk past them down the sidewalk once more. As she reached the turn where the rose bushes were, she turned back to the two bears with a smile.

"It was a pleasure to meet you both today! I do hope we'll be able to meet properly in the near future~" And with that, she was gone. Pop stood watching where the mouse had been standing previously.

As odd as it may have seemed there was something about her that gave Pop a feeling. A feeling he didn't quite understand. He didn't recognize her. Was there any reason to feel anything with her brief presence? On top of it all, he didn't even know her name! But here he was, standing with this feeling that felt as if something was pulling him. Tugging him to know who exactly that red mouse was.

He shook his head and looked down at his son who was now pretending his branch was now a magic wand, waving the single red leaf around in the wind. Despite his near heart attack of losing Cub, he couldn't stand to stay mad at him. So, Pop breathed a sigh before speaking.

"Hey kiddo it's getting late, why don't we start heading home? I'll get us some ice cream on the way how's that sound?" Cub shot his tiny paws into the air and hollered with happiness! Ice cream oh heck yes! So, Pop took Cub by the paw and began their walk to Cro Marmot's Ice Cream Parlor.

°• Time Skip !•°

It had been a few days after the park visit. The sun had taken a break that day to allow for some much-needed rain to tend to the thirsty greenery around the town. This left Pop and Cub to spend their day inside watching movies and playing games. They had been in the middle of a game of Cub Knight and Pop Dragon when the phone rang. This, of course, made Cub let out a disappointed "aww" in protest.

"No worries son, I promise I'll be right back," He explained as he stood to pick up the phone

"Hello? Pop speaking," It didn't take long to recognize the voice on the other line. The high and happy tone was all too familiar to mistake.

"Heyya Pop! It's Giggles! Sorry if this is a bad time,"

"No, not at all. What did ja need?" Pop asked patiently.

"Weeeell... I was calling to talk about this Friday. The day you wanted me to help babysit Cub," Her tone became increasingly guilty.

"Yea, what seems to be the problem?"

"Well...*sigh*, things came up recently at the hospital and they are wanting me to come in Friday due to the upcoming rainstorm that Sniffles is saying will cause quite a rise in injuries and illnesses. So, I have to cancel on babysitting Cub as much as I hate to say it," Giggles apologetically explained. She meant no harm in her explanation and Pop knew full well that it would be in her right to go help those in need. But it still was disappointing news, to say the least.

"Oh... I understand Giggles. Thank you for telling me. I'll try to see if I can find anyone who can take over. Take it easy on your shift," Giggles could hear the disappointment in Pop's acceptance but there was nothing she could do. She thanked him before hanging up, leaving Pop to contemplate who could take on a last-minute babysit. He pressed the bridge of his heart-shaped nose and massaged it thinking. He took a moment to check Cub who was playing with a stuffed pink hedgehog. That gave him an idea! He tapped the familiar phone number into his cell and listened patiently to the rings.


"Heyya Flaky, It's Pop."

"Oh! Hey Pop. Wha-what's up?" Flaky had been a good friend of Pop thanks to Giggles greeting. Though they were very shy, Flaky was very easy to talk to and on many occasions had been helped with Cub. They had also been the one to invite the two bears to Cuddles' baseball game. So, when Pop was ever in a pinch, he'd go to them.

"Flaky I'm in kind of in a dilemma. You remember that doctor's appointment I've got tomorrow?"

"Y-yes I remember," Flaky replied

"Well, I had Giggles babysitting Cub while I was out but now, with the weather being as it is. She's being called into the hospital for a full day shift to help with the patients. So now I have no one to keep watch of Cub,"

"Oh d-dear! That IS a d-dilemma,"

"So, well, I wanted to call to see if... Maybe you could come and watch Cub?" Pop nervously chuckled.

"Oh, Pop I'm s-so sorry but I just c-c-can't. I had already made p-plans with my partner that h-has reservations involved. As much as I w-would like to move the d-dates around, (F/L) worked way to h-hard on getting the money to afford them" Flaky explained with a heavy heart.

"Oh God your right! Its yawl's anniversary this weekend! Gosh, I'm so sorry Flakes I totally spaced..." Pop apologized quickly.

"Oh, Pop doesn't w-worry 'bout it. I should be t-the one apologizing, I'm usually always open to help babysit. But 'course there had to be that-that one time"

"Haha Nah, your good. Honestly, despite it all I have to say, you're one lucky porcupine Flakes. You got quite the lover wrapped around your finger, haha!" Pop explained playfully.

"Heh heh ya ya I'm p-painfully aware hehe," They calmed their snickers and sighed. There WAS a reason they were talking after all and that problem was still unsolved.

"Welp, shoot...I have no idea what to do now," Pop didn't mean to make Flaky feel guilty but it made no difference. Flaky felt bad about it.

"I am v-very sorry Pop. so, so sorry..." They both stayed silent for what felt like a few minutes when Pop heard Flaky gasp loudly.

"W-Wait! P-Pop I m-m-may know someone who could b-babysit!" Flaky exclaimed with the excitement in her tone.

"Wha- Who?" Pop answered.

"I- I met someone a f-f-few weeks ago! I d-don't think you two have met yet b-but she's very kind and l-loves working with children! She j-just moved into town about a month or t-two ago. I'm s-sure she'd love to babysit Cub for y-you," Flaky smiles through the phone Pop could tell.

"Moved into this town, huh? What a decision Haha but wow! If she could that be fantastic!" Pop exclaimed graciously

"I-I'll call her now! I'll t-text ya back to let y-you know her answer! Bye!" Flaky hung up before Pop could say goodbye back. He stood thinking of who this new someone could be. there seemed to be a bunch of new residences lately like the mouse with the weird tail he had met prior. He mentally slapped himself the moment he realized he hadn't asked for this possible new babysitter's name, just as he never got the name of the red mouse either. Man, he was bad at that...

He was taken out of his thoughts when he felt small paws pulling at his robe. He found Cub looking up at him with a very familiar look.

"Daddy, I'm hungwy," He said. Pop smiled at him but before he could reply he saw Flaky had sent him a message.

F. Spikeball.:💬I told ya she'd be happy to do it! She'll be over by 12pm exactly!

Pop smiled even wider at this knowledge then looked back down at Cub.

"Hah alright, alright! So am I. How does some PB&Js with Honey Crunchy Chips sound?" Cub replied in happy babbles as Pop picked him up to take them both into the kitchen for a well-deserved lunch.

°• Time Skip !•°

It was now 11:30 am on Friday. As expected, the rain was pouring stronger than the day previous so there wasn't much commotion going on outside.

Inside the bear family's residence, Pop was pacing back and forth praying that the mystery babysitter would still be arriving. It was still early, yes, but knowing the town for what it is and this was a fairly new resident in the community, the thought of a possible incident causing her to be late or not arriving at all was dreading on his mind. Pop did NOT want to take Cub out in this weather and certainly not into the doctor's office. Cub was terrified of the doctors.

He watched his wristwatch like a hawk as he sat with Cub who was finishing a bowl of sliced bananas and apples for breakfast.





Huh. Almost nineteen minutes early? Pop stood and walked to the door praying that it was the babysitter. With a deep breath, he opens the door...

"Hi, there! Is this the home of Po-OH! Oh, it's you again!" Pop was stunned. It was none other than the red mouse from the park!

"Uh wh-I ," Pop clears his throat. " I'm sorry I wasn't expecting the mystery someone Flaky mentioned to be you! How perfect timing this all is, huh!? hahaha," Pop stammered but laughed.

"I know right! It is a small world out here hehehe," she giggled.

"Well, I think it's time we formally met," She held her right paw out.

"My name is Skippy, Skippy Roo. I live near the bay shores behind Petal Park. Flaky told me she let you know I moved here not too long ago and, yea! So far it's been quite the 'journey'," She nervously laughed which automatically pointed out just what she meant by "journey". Pop shook himself of his state of awe and took her handshake noting how soft her fur was.

"Ahem Well, Skippy it's a pleasure to properly meet you! I'm happy to hear you'll be sticking around this crazy town and honestly, you have no idea just how much you coming on such short notice is to me," Pop greeted back thankfully.

"Aww, it's no problem at all! I'd come even in the worst of weathers if it would allow me to see the Lil sweetheart again! Speaking of which I don't believe I ever got his name either the first time we met," Skippy implied looking around behind Pop to see if he was near. Pop's heart was slightly touched by the kindness Skippy showed. Flaky wasn't kidding about her thoughtfulness, that's for sure.

"Oh! Where are my manners? Please, come in! You'll die of Hypothermia if you stay out here in the rain," Pop stepped to the side allowing Skippy to step inside. She looked around the living room while peeling off her grey pullover hoodie. Pop waited until she had gotten in to answer her question.

"My son's name is Cub! He's finished his breakfast in the kitchen. I'll take you around the house before I head out," He smiled before giving Skippy the home tour. It had not taken long before Pop took another look at the time and rushed out the door to make sure not to be late to his appointment. Cub had finished eating and saw that the red mouse lady he had met so long ago was at the door. He was BEYOND thrilled!

"SKIPPYY!" he ran to her feet. She turned to him and with a giant smile bent down and picked up the happy infant spinning him around in her arms.

"Well hello, you! Guess who's your new babysitter for the day?" Cub giggled with delight at her playful tone. He placed his finger on her nose.

"It you?" he asked giggling

"Thaaaats RiGHT! So, tell me Lil Cubby, what would you like to do now?" She asked him with an encouraging smile. Cub pause and gave an over the top thinking stance before shouting.

"Knight and Dwagon!" So, with that Skippy put Cub down and they played the afternoon away with lots of laughs and smiles.

It wasn't until 11:30 pm Pop was treading up the road to his home tree. Trying to make it in the rain to the hospital was an absolute nightmare, but the actual appointment was even worse. Mole wasn't the best choice for a doctor's assistant and we'll leave it at that.

He was hungry, in pain, and soaking wet from the still pouring rain. But he was so happy to finally be home... that was until a thought crossed his mind. What if something happened while he was gone. What if the babysitter didn't make it and Cub got hurt afterward? Or worse, they both died due to some sort of household accident outside of their control! Now he was in a panic stumbling as he attempted to unlock his front door.

Pop walked in expecting blood, guts, and gore but was greeted to Skippy reading peacefully on the living room couch next to the nearest lamp shade. A delectable scent wafting in the air. Skippy turned to Pop with a warm smile stretched to his greeting.

"Welcome back. I'm happy to see you made it home safe," Skippy whispered as she closed her book gently.

"Yeaaaa heh. It's a long story but I won't bore you with the details. Why are we whispering? Where's Cub?" He whispered back. Skippy smiled and gestured for Pop to come closer. He did so, walking to the couch. There he saw his son curled up in Skippy's tail along with his favorite blanket draped over him.

"He refused to go to sleep without me there. So, I decided I'd let him lie with me while I read him some stories. He fell asleep instantly but as soon as I tried to take him to his room he'd run straight back and cozy up next to me. So, I figured I'd leave him. I hope you don't mind."

"I don't mind at all." Skippy looked back up to Pop and noticed his eyes were partially glistening to the dim light of the lamp. His smile full of happiness causing her to smile wider.

"So, it's been a good day then?" Pop asked.

"Oh yes. A day full of Knights & Dragons, hide & seek, PB & j's and storytime. It was a very fun-filled day," Skippy confirmed and slowly began to wriggle her way out of Cub's grasp so she could say her goodbye's. It took a good moment to steal back her tail and replace the missing space with a plush pillow to keep his neck supported while Pop and her talked.

"Now before I go, I took the liberty in making you some baked salmon for dinner. I didn't know whether or not you'd be able to eat on your way back so I decided to make something just in case," Pop was blown away. Skippy took the time not only to last-minute sit Cub but also make him dinner? He didn't know how to react!

"Skippy you didn't have to," he said, touched. Skippy smiled wider (that was even possible at this point).

"Of course, I didn't HAVE to, but it was the least I could do," she started to walk to the door and pull on her sweater on.

Odd. That feeling was back but it was different now. It almost made him want to..stop her? He walked to her catching her attention.

"Skippy, If I may...," he paused thinking over his words. She watched in confusion.

"D-do you like bowling?" Skippy's smile returned tenfold.

"Oh yeS! *cough* oops haha yes I do!" Skippy corrected her volume looking at Cub's still sleeping form.

"Would you like to join us sometime for a bowling day? I'm sure Cub would enjoy the new company. I mean...If you're for it," Pop was nervous asking. This was out of nowhere and never had he really wanted to get to know another woman since his late wife even as a friend. But Skippy... Had just placed her paw upon his left shoulder. He didn't realize he was staring at the ground 'til he found his path back to her warm smile and velvet eyes.

"I'd love to join you two, so what do you say? This coming Wednesday?" She offered.

"Oh, Yea! That sounds great," They both agreed and soon, just as Skippy had turned passed those rose bushes in the park, she was gone. Back to her home past Petal Park, near the bay shores. As he closed the door behind his button tail Pop looked to a photo of him and his late wife. He smiled at it painfully for a moment.

He caught a look at where in the picture his wife's eyes were directed at and followed to where Cub was. Asleep on the couch smiling from his sweet dream. He smiled and placed a kiss on the photo before picking up Cub gingerly to lay him in his bed.

He then made his way to his bedroom removing his hat and laying down on his large king mattress. As he closed his eyes memories of Skippy swarmed his mind.

"What a way to meet someone special," His wife's words rang as he fell into a peaceful, dreamless slumber.

"It's only a matter of inches, but skipping gets me just that much closer to heaven."

Quote: Terri Guillemets

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Stay tuned for part 2,

Pop Goes My Heart:D!