A/N: This idea was based on an observation from myself and a few other fans out there who have noted that (Lynn aside) Leni is the only older Loud sister who appears to not be in a committed relationship, in spite of the fact that she had a canon love interest (apparently Lynn was just dehydrated). You guys know how I am: if there are uncharted waters that are begging to be delved into and explored further, then by George, I'm diving in! As noted, this story takes place during season four, and is also retroactively AU - I'll explain why later.

I would also like to extend credit to this community's queen Leni fan, PlasticPencils, for taking the time to Beta Read this for me, as well as contribute input and suggestions to make this story even better… speaking of which, if you haven't, please take the time to check out some of her stories as well, such as Deep Inside Me (of which I Beta Read for her) or Shades of Blonde – you will not be disappointed. Also credit to CrypticMoonFang for her notes on correcting several grammatical errors.


The Louds were a family of one boy and ten girls, ranging in age from seventeen years all the way down to fifteen months. Each of the Loud sisters were striking and endearing in her own way, but among the sisters who clearly stood out and shone a little brighter than the others was the second-oldest of the brood – sixteen-year-old Leni. Leni was a pretty, perky, bubbly, and charismatic young girl whose heart was as golden as the hair on her head, and was as sweet and gentle as the days were long; she is presently a junior at Royal Woods High School, while also holding a part-time job working in the Reininger's department store at the Royal Woods Mall. With her good looks and positive personality, it was no surprise that she had a number of friends who absolutely adore her, such as two of her closest friends, Miguel and Fiona, whom she not only attends school with, but are also her co-workers, and the three of them often hang out together; meanwhile at home, she considers oldest sister, Lori, to be her best friend, confidant, rock, and biggest hero. That is not to say that Leni doesn't also maintain any bonds with any of her other siblings – quite the contrary, she absolutely adores all of her siblings, and would do anything she possibly could for any of them, no matter what the circumstances were; regardless of her busy schedule, if she is able to, she will engage in whatever activities her other siblings were willing to include her in, even if she did not quite understand the concept of some of them.

Still, she loves spending time with her family more than anything, and is always ready to engage in any activity with them. On one random Saturday afternoon, she had nothing on her plate to keep her busy, and decided to see if any of her siblings were in the mood for her company… starting with the big sister she shares a room with.

"Lori, let's do something together!" Leni happily offered.

The older blonde was sprawled across the top of her bed, her nose practically glued to the screen of her mobile device, as was per usual with her. "Some other time, Leni; I'm waiting on Bobby for our weekly FaceTime…"

Sure enough, Lori's phone alerted her of an incoming video call, which she gladly accepted, revealing the face of her long-distant boyfriend.

"Hey, Babe!" he greeted her on the screen.

"Hey, Boo-Boo Bear!" she squealed.

Leni did look just a tad disconcerted, but she knew there were still plenty of other siblings she could spend time with. She arose from her bed, and stepped out into the hallway just as two of her younger sisters had stepped out of their room from across the hall.

"Hey, guys!" Leni greeted them.

"Hey, Leni," they responded, without looking up at her as they made their way over to the stairs.

"Where are you two going?" Leni asked. "I thought maybe we could hang out together."

"Maybe another time, brah," said Luna as she slid down the railing of the banister. "Me and Sam got ourselves a serious jam sesh today!"

"And me and Benny are meeting up for Shakespeare in the Park," added Luan, before she, too, slid down the railing, and followed her roommate sister out the front door.

Leni merely stepped over to the top of the stairs and saw the front door closing from where her younger sisters had already departed their residence, even though she still bode them a reluctant farewell, as she mumbled, "Okay, well, have fun then…"

By this time, the teen was feeling a little more dejected, until she heard a voice coming from one of the bedrooms down the other end of the hallway. She stepped over to the door that was cracked open and peered inside to see her little sister Lola had gathered her stuffed animals and dolls around the little round table that was on her side of the room, as she hosted another one of her little tea parties.

"Who would care for a cucumber sandwich?" Lola asked her plush party guests.

"Oh, are you having another tea party, Lols?" Leni asked as she opened the door a little wider.

Lola looked up at her big sister standing in the doorway, initially with a look of annoyance across her little face, as she chastised, "Leni! How rude of you to interrupt us!"

"Oh, I'm sorry, Lols," apologized Leni. "I just thought maybe I could join you."

The look of annoyance was quickly replaced with a big, gap-toothed smile, as Lola said, "Oh, why of course you can join us; we would love to have you!"

The little pink princess nudged some of her stuffed animals aside to allow room at the little table for Leni to join in on the tea party, to which the teen happily sat down on the floor on the opposite side of the table – which was a little too low for her, but she made the best of it, while she squealed, "This is so much fun!"

"Would you care for a cucumber sandwich, Leni?" Lola asked, as she presented a little platter of finger sandwiches before her big sister.

"I would be delighted," said Leni, as she took a tiny sandwich from the platter, and began to sample it with tiny, dainty little nibbles.

Lola proceeded to pour some imaginary tea from her little porcelain tea pot into a little tea cup that rested on the table in front of where Leni was sitting. "And, how many sugars would you care for in your tea, one or two?"

"Oh, actually, I would care for artificial sweetener," said Leni as she pat her perfectly flat tummy. "I'm watching my weight."

"Ooh, smart girl!" Lola said, much to Leni's delight.

Lola pantomimed opening a little packet of sweetener and sprinkled it into Leni's tea cup, of which her teen sister happily took into her hand and prepared to take a sip of her make-believe tea, that is, until the little pink princess cleared her throat loudly to gain her attention.

"Uh, Leni, aren't we forgotten something?" Lola asked.

Leni gasped, "What? What are we forgetting?"

Lola held up the smallest digit on her little hand and stated, "Pinky?!"

Leni realized she was overlooking this little act of etiquette while drinking her imaginary tea, as she extended her pinky from the handle of the tea cup before she took a sip; this satisfied her little sister who smiled.

"Oh, this tea is totes divine, Lols!" Leni said while playing pretend with her little sister.

"Thank you, Leni; I made it myself, it's a secret recipe!" Lola said.

"Oh?" Leni asked. "Do you think you could share it with me?"

Lola furrowed her brow and muttered, "I can't do that; it's a SECRET!"

As Leni went back to sipping her imaginary tea (while she kept her pinky extended), Lola turned her attention to the lilac-colored teddy bear immediately to her right.

"What's that Mrs. Gumdrop?" She leaned in closer to her teddy bear, as if she was listening with great interest in what this plush toy had to say. "You want Leni to make your wedding gown for you? Oh, I know she'd love to!"

Leni returned her tea cup to its little saucer, before she rested them on the table below her. "Huh? Wedding gown? What wedding?"

"You haven't heard the biggest news of the century?!" Lola scoffed as she scooped up the lilac teddy bear to her right and the brown teddy bear to her left. "Mrs. Gumdrop and Mr. Sprinkles are going to tie the knot!"

"I didn't know teddy bears could tie knots," said Leni cluelessly.

"I mean they're getting married!" Lola exclaimed.

"I didn't even know teddy bears could get married either," added Leni.

"Well, they are, and Mrs. Gumdrop would like for you to make her the most spectacular, magnificent, luxurious, opulent, dazzling wedding gown ever!" Lola exclaimed.

After she had witnessed three of her other sisters preoccupied with their own romances, Leni was really not in the mood for any more of this - even if the romance Lola spoke of was make believe. She arose from the floor and mumbled, "Yeah, okay…"

The teen proceeded to walk out the door, before the little princess called out to her, "Hey, where are you going? We're not finished! Mrs. Gumdrop wanted you to consult with her about how long the train should be!"

"She can slip the notes under my door, I'll look at them later," said Leni as she stepped back out into the hallway.

Lola scoffed once more, "How rude! My apologies, my friends; sometimes my dear sister, Leni, doesn't know how to use her brain."

As Leni slowly trudged down the hall to return to her own bedroom, she paused halfway when she heard a soft, deadpan voice in the room to her right, as the little goth girl residing within was reading aloud the words she had written down; undoubtedly another new poem:

Love
What is this feeling we come to possess?
One over some obsess?
Causing some hearts to sing?
Yet causing others to sting?
Delicate as a the wings of a butterfly
Yet forceful as the winds of a hurricane
Soft as a vampire's sigh
Yet hard as a

"Hmm," Lucy paused as she hit a stumbling block in her writing. "What would be a good rhyme for 'hurricane'?"

"Sigh," Leni mumbled as she returned to her bedroom, which she saw was now empty due to Lori's absence; she may have overheard her roommate say something about meeting up with her friends Carol and Whitney later, or something to that effect, but she hadn't paid much attention.

The teen crawled atop her bed, flopped herself down, and wallowed in a well of self-pity; even with a large and loving family, and a sizable circle of friends who adore her so, there was still one thing Leni felt she was missing her life: a significant other. Older sister Lori had been going steady with Bobby for quite a long period of time, and they have frequently spoken about their future together of getting married and having eleven children of their own. Younger sisters Luna and Luan have also been with their respective sweethearts for a number of months as well; Luna had been dating her bandmate Sam for almost a year now; Luan had a crush on Benny since middle school, and finally started going out with him since they played Romeo and Juliet back in the fall. Even certain younger siblings seemed to have some form of romance going on in their lives, even if they were rather unconventional, such as Lincoln juggling feelings for a few different girls, Lucy apparently crushing on two different boys in addition to her fictional husbando Edwin, and Lola having quite a string of admirers in her first grade class. And yet, Leni had no one.

Leni Loud was a great first date… not so hot on the third.

Assuming she even made it to a third date with someone.

It was not too surprising that adolescent boys at Royal Woods High found the tall, pretty, and lithe blonde to be irresistible; many boys enjoyed going out on a first date with her, and would take her to a variety of different places, ranging from the movies, the park, the mall, or even one of the many fusion cuisine restaurants in town. During these numerous first dates, almost every boy who had asked her out soon came to realize that brain power was not particularly a strength of hers… Some boys would attempt to charm her with a sense of humor, only for many of their jokes to fly right over her head, or for her to interpret their puns far too literally; in trying to carry on a conversation, she had a tendency to ramble nonsense; and, on some occasions, her short-term memory would cause her to forget her dates' names altogether. Certain boys would chalk her behavior up to being nervous about having a first date with someone she had only gotten to know, and figured that, surely, a second date would go a lot smoother… unfortunately, that was rarely the case, as her ditzy, absent-minded behavior would persist, thus she would unwittingly personify a typical dumb blonde.

She was a great first date… not so hot on the third.

That seemed to change when Chaz entered her life.

Chaz was certainly not the type of boy many high school girls would want to go out with: the short, round, curly-headed, freckle-faced nerd was actually among Lori's circle of friends, and he rather enjoyed spending time not only with her, but many of her siblings as well; whether it was reading Ace Savvy comics or playing video games with Lincoln, sitting in on Luna's jam sessions or Luan's comedy shows, he always voiced his enjoyment with his simple catch-phrase, "Chaz like!" From the moment he first laid eyes on Leni, he found himself infatuated with whom he felt was Lori's prettiest sister; at the same time, there was something about Chaz that made Leni realize she was also smitten with him as well. He was one of the very, very few boys she managed to make it to a third date with, and not only that, he was also the only boy who continually kept in contact with her: it was not at all uncommon for him to send her occasional texts flirting with her, and he was almost always the first one to react to her new posts and pictures on social media (usually with heart emojis). In addition to going to the same school, Chaz had also eventually gotten himself a part-time job at a neighboring department store at the Royal Woods Mall… if either he or Leni happened to spy one another from their respective places of employment, they would wave to each other from afar, and if the breaks in their schedules would allow for it, they would meet together for a quick bite at the food court. Finally, Leni felt like she had found her significant other.

After a while, Leni stopped receiving such flirting texts and IM's from Chaz; likewise, she also noticed she was receiving far less reactions from him on her new social media posts and pictures; and it even seemed as though he was actually avoiding her at school and at work. She didn't think much of it at first, but the longer she went without hearing anything from him, the more she felt like maybe things were over between the two of them. Some days, the thought never really crossed her cavernous mind, but on a day like this, when it seemed like almost all of her siblings were preoccupied with entertaining the concept of romance in one way or another, it made her wonder if something was wrong with her that she was unable to hold onto a steady sweetheart, unlike some of her siblings.

She must have lost track of time, because the next thing she knew, she awoke to a voice calling out to her.

"You're sleeping already?"

Leni shot her eyes open and sprung into an upright position on her bed to see that her roommate had returned from whatever engagement she had prior to said return. "Huh? Oh, no… actually, I was just… thinking…"

Lori looked both surprised and amused, as she decided to rib her sister a little: "Carefully, Leni; if you think too hard, you could lose your hair."

Leni gasped as she wrapped her arms around her head and shrieked, "I don't wanna lose my hair!"

"That was literally a joke," Lori assured her.

"Oh…" was all that Leni mumbled, before she wrapped her arms around her knees instead. Lori was her best friend, confidant, and rock; she was probably the only person she could talk to about her problems. "Lori? What's wrong with me?"

"How should I know?" Lori responded to such a vague and unspecific question.

"There must be something wrong with me," said Leni. "I thought maybe you would know."

"Well, I don't…" said Lori with a shake of her head and a shrug of her shoulders. "What makes you think something's wrong with you?"

"Because I can't keep a steady boyfriend like everyone else…" said Leni.

Lori eyeballed Leni for a moment before she resumed the conversation, "So? Lots of girls can't hold onto a steady boyfriend, that doesn't mean there's anything wrong with you."

"But, Lori, I'm sixteen… shouldn't I have a steady boyfriend by now?" Leni asked.

"It's not like going to R-rated movies, Leni," said Lori. "You don't have to be a specific age to have a boyfriend, or even be in a relationship."

"But, Luna and Luan are younger than me, and they've been in relationships, too…" Leni pointed out. "And you've been with Bobby, like, forever! How come you, Luna, and Luan managed to get steady sweethearts, but not me?"

"Well… we just… got lucky, I guess…" said Lori; at first she felt a little awkward about the phrase she just used, considering it also is frequently used as an innuendo for something even naughtier, but she reminded herself this is Leni she's talking to – she wouldn't understand what an innuendo is, anyway.

"So, I'm unlucky then?" Leni asked.

Lori finally walked over and sat on the edge of Leni's bed. "No, Leni; it doesn't mean that at all… not everything happens at the same time or same age for everybody… and there's literally nothing wrong with not having a boyfriend or being in a relationship right now…"

"But, why?" Leni asked again. "So many boys ask me out on dates, but none of them want to keep seeing me…"

Lori silently sighed through her nose; she pretty much had a feeling why this was the case with her roommate, but she was unsure of what angle to approach the discussion from – that is, until Leni pressed another question on her...

"Lori? Am I a retard?" Leni asked.

The oldest sister was stunned to hear this question coming out of her little sister's mouth from seemingly the clear blue... but, obviously, this was not a question that came from out of nowhere - somebody had to have told her this at some point for her to even consider it being who she is.

"Who told you you're a retard?" Lori asked.

"I hear people at school talking about it… they say things like, 'Leni Loud is such a retard!'" Leni looked over at her roommate and asked, "Lori… what's a retard?"

Lori had a very uncomfortable look on her face. Regardless of its context, the use of this particular word was still improper and mean-spirited - no matter how she tried to explain it, she knew it would not sit well with her younger sister... still, she inquired, and was looking to her big sister for an answer.

"Leni…" Lori hesitated while she pulled at her fingers. "They're saying that you… that you're… well… that you're…"

"What? I'm what?" Leni pressed; she really wanted to know what this 'R' word meant.

When she saw there was no sense in dancing around the question, Lori sighed and finally came out with it: "They're saying you're stupid, Leni…"

Leni gasped and her eyes widened. That hurt; that really hurt. She insisted, "I'm not stupid!"

"No you're not, you are not stupid," agreed Lori, but trying to find a gentle explanation for why her sister is the way she is was certainly not an easy task either. "You're just… y'know…"

"Stupid…" Leni pouted defeatedly.

"No! You are not stupid! You just… you think differently than most people…" was the best way Lori could think to put it.

"I guess that's why boys never want to keep going out with me," Leni continued to pout, as she rested her chin onto her knees again. "Because I'm just a great, big, stupid, stupid head."

"Leni, you're not stupid; you're very smart…" Lori reached over and rubbed her sister's back, as she tried her hardest to think of how she could try to convince her otherwise. "I mean… literally nobody knows how to make dresses like you…"

Leni mumbled, "Yeah..."

"And smoothies! Who knows more about making smoothies than you?" Lori asked.

"Nobody I know…" said Leni, with a little shrug.

"And how could I forget woodworking?" Lori added. "Even Lincoln had a lot of trouble with it for a class assignment – that takes a lot of skill!"

"Really?" Leni asked as she turned to face Lori.

"I mean, you'd have to literally be smart to know how to do any of that stuff, wouldn't you." Lori asked.

"Yeah... I would," said Leni as she finally revealed a small smile.

Lori began smiling as well, as she continued to rub Leni's back. "So, see? You're very smart in your own, unique, Leni way!"

"Yeah... I am!" Leni exclaimed, as if her older sister had magically flipped a switch in her disposition.

The oldest sister hoped that her words of encouragement would do the trick to lift up the spirits of her younger roommate... until the two teens heard a certain raspy voice out in the hallway cheering, "Yippie Skippy!" belonging to the Loud family's resident handy sister as they witnessed her skipping down the hall.

"What are you so excited about, Lans?" Leni asked; she wanted to be able to share in her little sister's excitement, whatever it was.

"Skippy just asked me to go to the biking fair in Tall Timbers Park with him!" Lana squealed as she ran past their bedroom door into the bathroom.

"Skippy?" Lori asked. "Oh, you mean the little bike whiz you've been crushing on?"

"Yeah!" Lana called out from inside the bathroom. "I guess this'll be kinda like our first date!"

A flush was heard, and the two witnessed their scrappy little sister run back down the hallway in the opposite direction, of which she presumably slid down the banister to the first floor to fly out the front door to join her crush at the biking fair they would be attending together. All of which seemed to cause Leni to bottom out all over again, as she fell back onto her pillow and sighed loudly.

"See, Lori?" She asked. "Even Lana has a little sweetheart, too!"

Lori felt her efforts in lifting Leni up came crashing right back down after that brief little episode; she sighed and asked, "Why does it really matter to you that much, Leni?"

"I just wish I had somebody who loves me, and wants to spend time with me, and wants to go places with me…" Leni explained.

"Leni… you already have people like that…" said Lori. "You literally have twelve other people in this house who love you, and care about you, and spend time with you… and look at all the friends you have at school and work… you literally don't need a boyfriend for that!"

"I know, but… it's not the same… this is different…" insisted Leni.

"Okay, then explain it to me..." said Lori, while she rested her hand on Leni's shoulder. "What's different about it?"

"How does Bobby make you feel?" Leni asked.

Lori shrugged a little. "Special?"

"That's it…" said Leni. "I want somebody who thinks I'm special to them…"

Lori tried in earnest to lift Leni's spirit again. "Look, Leni… just because I have Bobby, or Luna has Sam, or Luan has Benny… it doesn't mean you have to have a boyfriend now… it works differently for different people… sometimes it takes longer for some people, it's literally nothing to worry about."

"Maybe…" said Leni. "But… I've seen how happy you and Bobby are… and how happy Luna and Sam are… and how happy Luan and Benny are… it's like you all are just so… perfect for each other… I just wish it was like that for me…"

"Leni, there's no such thing as a perfect relationship," said Lori. "And like I said, it's okay if you're not in one now; you've got so many other things in your life to worry about not having a boyfriend."

"I guess so…" said Leni while she stared at the ceiling. "But, I still wish I had somebody to share my happiness with."

Lori released another silent sigh through her nose; if only there was some way she could show Leni that there is really no need for her to obsess over not having a steady significant other like she or their sisters – maybe even show her that not all relationships are perfect, that may even change her mind. After thinking about what Leni had just said about seeing how happy she, Luna, and Luan are with Bobby, Sam, and Benny, respectively, Lori had an idea come into her mind that could very well have the desired effect she wanted for Leni.