9.36: Happy Endings

Note: Real quick before we dive-in, I have a bit of good news! I’ve managed to get a chapter ahead, which means for the time-being, we are back to a once-a-week update schedule (Wednesdays). I can’t promise how long it will last. Could be just the next few weeks, could be longer… But either way, I’m gonna keep you all updated if things change (let’s hope they don’t though!). And, if a miracle occurs and I can somehow swing TWO a week again, you all will be the first to know, I promise 😛 

And now, without any further ado… Welcome to the Adult Arc! 🙂


Asher’s lips stretched wide into a yawn as he groggily made his way up the short walkway toward his front door.

Despite his exhaustion, he’d been aware enough of his surroundings to take note of the unfamiliar vehicle parked on the street outside. The sight was unsurprising, but that didn’t make it any less annoying. No matter how many times he told her otherwise, every couple weeks or so, Penny would bring a complete stranger to spend the night at his home.

Asher was certainly in no place to judge his sister for what she was doing (though he made it a point not to dwell on the specifics too much), but would it kill her to go back to the guy’s place every once in a while?! Especially when this wasn’t even her house?!

This is what I get for feeling sorry for her… The next time she needs a place to stay, she can go back to Mom and Dad, he thought bitterly, though part of him knew it was an empty threat. Much as he couldn’t stand her growing up, his and Penny’s relationship had actually been getting a lot better over the past several years… until the past few months, anyway.

Now that they were living together, so much of that old bitterness and resentment they’d once harbored for each other had begun bubbling up to the surface once more. What else could he have done though? Penny was his little sister. He’d had no choice but to help her out. Ugh.

Fortunately, as usual, she’d chosen to bring her date home on a night when Asher had been working late at the hospital. He would be asleep by the time the stranger left, and he’d have a few hours of decent sleep in him before getting into the inevitable screaming match with his sister.

Asher hung his car keys on the hook by the door, flipped a nearby light switch, then immediately removed his tie and button-up shirt, eager to be rid of them and change into more comfortable clothes. He left them thrown on the floor to be dealt with later. Right now, what he needed was sleep

It wasn’t until he’d made his way toward the bottom of the stairs that he heard it, and Asher stopped dead in his tracks at the sound. The soft squeak of a mattress; the rhythmic pounding of a headboard against a wall; and, worst of all, sounds no one should ever hear their sister making in their life.

Are you fucking kidding me?! It’s four am! Torn between disgust, embarrassment, and rage, Asher stood there for a few moments longer, weighing his options and trying to block out the persistent sounds carrying down from the guest bedroom.

He could burst in and confront Penny, but that would mean not only hearing his sister, but seeing her in a way he never wanted to imagine. It would only make things worse. Even knocking or shouting through the door would just escalate things, and that evening’s shift had left him much too exhausted to deal with that right now.

He could simply wait it out — put on some headphones, try to ignore it, and hope they finish up soon… But how could he know whether this would be their last round or not? If they were still going at it at four o’clock in the morning, who the hell knew?!

The third option was to simply leave. As ridiculous as it felt to be essentially kicked out of his own house, it seemed like the easiest option at the moment — get away, get some sleep, deal with it later. But where could he even go? Check into a hotel for a few hours? Sleep in his car?

Before he’d even completely made up his mind, Asher was already making his way toward the door. He was tired, he was frustrated, and at that point, he just wanted to get away.

As he grabbed his car keys and stepped back out into the cool early-morning air, another option crossed his mind — somewhere else he could go for a few hours before he came back home and confronted Penny. There was only one other person Asher knew who would be awake at this hour.

He pulled out his phone and sent a desperate text, hoping to hear a response.

And luckily, within just a minute or two, he got one.

Asher was comfortable enough to just let himself in when he arrived at his friends’ house — they had been expecting him, after all. 

Reece and Lily were both sitting at the kitchen table, drinking their morning coffee. Lily was still in her pajamas, but her husband looked ready to walk out the door already.

At the sight of her friend, Lily rose to her feet to go give him a hug. “Oh my God, you poor thing! Come sit down.”

Asher smiled gratefully as she pulled away from him, and he followed her back to the table. “Thank you. Seriously. I’m so sorry to show up like this, but, uh… Well… I explained it to Lil already.”

Reece let out a low chuckle. “Yeah, she filled me in… Jeez. Y’know, this whole thing would be pretty funny if it weren’t so…”

“Horrifying? Disturbing?” Asher forced a tired smile. “Or humiliating?”

He laughed again. “All of the above, I guess.” Reece paused before continuing. “Hey, do you want some coffee?”

Before Asher had a chance to reply, Lily cut-in. “Baby, he just worked an eight hour night shift at the emergency room… He needs sleep, not caffeine!”

“Okay, fair… Well, help yourself to anything in the liquor cabinet, then!” 

Asher laughed. Reece was always so warm and generous, even if he could be a little awkward sometimes (though Asher knew he was guilty of that too). 

“I’ll probably pass… But thank you.”

“Well, if you’re sure…” Reece gave a shrug before quickly downing the rest of his coffee. “Sorry not to stick around, but I’ve gotta run.”

“This early?” It was barely five am, and though he knew Lily and Reece were both ‘morning people’, he wasn’t expecting either of them to have to work quite this early.

Lily answered for him with a smile. “Huge conference call with some client in… Switzerland, right?” Her husband nodded in confirmation. “He’s been talking about it all week!”

“Well, if we make this deal, it’ll be huge! Too bad timezones are such a pain in the ass…” Reece rose to his feet. “Anyway, speaking of pains in the ass, sorry about your sister… You’re always welcome any time you’ve gotta escape!” He smiled at Asher for a moment before turning to his wife. “See you tonight. Love you.”

Lily got up to give him a kiss on the cheek. “Love you too… Go kick some ass!”

“Will do!” With one last little wave toward Asher, he headed toward the front door, grabbed his car keys, and disappeared out into the darkness.

As soon as her husband was gone, Lily sat back down at the table and gave Asher a strange, almost searching look before letting out a heavy sigh.

“What?!” He asked defensively.

Oh Asher, that jerk dumped me and kicked me out and I have nowhere to go!” Though slightly exaggerated, Lily’s impression of Penny’s high-pitched whine was pretty good. “I can’t go back to Mom and Dad, it’s too humiliating! Can’t I stay with you? Just for a few weeks?”

Asher rolled his eyes. “Alright, Lil. I get it.”

Of course, by ‘a few weeks’, I really mean ‘three months’.”

“Actually… it’s almost four.” He admitted softly.

Lily ignored him. “Sure, Penny!” Her Asher impression was much less convincing. “I haven’t even owned this house for a year yet, but you know what? I’d LOVE an obnoxious roommate who lives here rent-free and brings random dudes home all the time!”

“I said I get it!” Asher snapped. “Fuck me for trying to be a good brother, right?”

“Sorry… Maybe that was a little harsh.” Lily admitted. “But you’ve gotta start putting your foot down with her! At least make her help pay the mortgage!”

Asher eyed her skeptically. “Penny’s a frigging part time barista. She makes minimum wage, and I’m making…” He hesitated. It felt awkward to bring up his salary. Asher knew he made more money than Lily did, despite only being out of his residency for one year. “A hell of a lot more than that.”

“Yeah, I get it, but it’s the principle of the thing!” Lily shook her head. “You’re too nice, Ash.”

“I know.” He sighed, rising to his feet. His momentary anger at her was already forgotten, replaced once more by gratitude. “Hey, do you mind if I kinda zone out and watch TV for a little while? And, uh… possibly crash on your couch for a few hours?” He added guiltily. 

“Duh. That’s why you’re here, isn’t it?” Lily smiled warmly at him. “You can even take the spare bedroom, if you want. I’m just gonna be showering and getting dressed and stuff.” With a shrug, she followed him to the living room. “And if I’ve gotta go before you wake up, don’t worry about it. I trust you not to trash the place while we’re gone.”

Asher laughed as she sat beside him on the couch. “I appreciate the confidence. Reece did say the liquor cabinet’s fair game though… Careful. I might start breaking shit!”

“Mmm… You can’t hold your liquor like you used to though.” Lily teased. “You’d be passed out after like two drinks!”

“Ha! Probably…”

Asher didn’t need a medical degree to know that your body gradually changed as you got older, but he’d always thought people were exaggerating when they said everything went completely to shit as soon as you hit thirty. But man… they weren’t kidding. Seven months in, and he was already feeling it.

“Look, in all seriousness… Please promise you’ll talk to Penny. And I don’t mean yell and scream at each other. I mean really talk. If she’s gonna keep staying with you, you’ve gotta set some boundaries.”

“I’m gonna try.”

“And, if all else fails… You can invite Matt over for a little revenge?” She wiggled her eyebrows suggestively as she spoke, earning a bright burst of laughter from her friend. 

“We’ve been on three dates, Lil! I’m not asking him to spend the night.” Matt was a fun guy, but Asher still wasn’t sure if he wanted it to turn into anything serious… And unlike Penny, in his eyes, inviting someone to spend the night was a pretty big deal.

“Oh… I thought you’d already, uh…”

Asher laughed once more, though he felt a touch of awkwardness this time. “We’ve… done a little more than kiss.” He confessed. “But we’ll see. I like him, but I’m still not sure about it.”

In truth, he’d agreed to Lainey’s insistence that he go on a date with her bandmate out of sheer convenience. During his residency, Asher had quickly learned that it was next to impossible to meet anyone on a doctor’s schedule.

“Well, if you wanna bring him with you Saturday, you’re more than welcome to.” Lily offered. “I wanna meet him!”

“After three dates? No way!” Asher shook his head. “‘Meet the best friend’ is almost as big as ‘meet the parents’. I’m not gonna bring some random guy to your birthday party! Especially not this birthday… Turning thirty’s a big fucking deal.”

“I know… I’m officially old now… Like you.” Lily stuck out her tongue teasingly. Her actual birthday had been two days ago, though she wasn’t celebrating until the following weekend. “Oh! And I forgot to tell you who actually remembered to text me and wish me a happy birthday!”

Asher’s brow furrowed. “Christie?” He guessed. “She’s usually pretty flaky.”

Lily shook her head. “Nope! Ollie!”

Asher’s eyes widened in mock surprise. “You were a witness to the rare and elusive Ollie birthday text? And it was on time?!

Lily grinned at him. “Like you said, thirty’s a big deal… even to Mr. Hot-Shot Lawyer, I guess.”

“True… he was on time for me last summer too.” Asher remembered. 

It was a nice change from the usual ‘I’m so sorry I forgot your birthday!’ message he’d get a week or two after the fact. At least Asher was always on time with his birthday texts.

But no matter whose birthday it was, for years, it had been almost exactly the same. Their birthday wishes would inevitably lead to a back-and-forth exchange about how it’s ‘been too long’, and they ‘need to catch up some time’.

Sometimes, if they were lucky, they’d even manage to get a phone call in before one of them dropped off the radar again… usually Ollie, especially these days. Married life had certainly kept him busy, and ever since his wife had her baby two years ago, he had dropped off the face of the earth worse than ever before.

Before either of them could speak again, Asher let out a heavy yawn. 

“Oh shit, I’m sitting here talking your ear off instead of letting you sleep!” Lily sprang up from the couch. “Get some rest, okay? Lemme get you some pillows and a blanket… And are you sure you don’t wanna use the guest room?”

“I’m fine on the couch.” He smiled up at her. “And honestly? I don’t even need any blankets or anything. I’m seriously good. Go get ready for work.”

“Are you sure?”

Asher nodded.

“Okay, well… Goodnight! Or, uh… morning.” Lily gave him a little smile before finally heading up the stairs, turning the light off behind her as she went.

He settled back on the couch, feeling a sense of drowsiness wash over him in the dim light. Just one more late night shift and he’d be done for the week, then next week he was back to a fairly normal schedule for a while… and he couldn’t wait.

Asher retrieved the remote and began absent-mindedly flipping through channels, looking for something to leave on in the background while he tried to get some sleep. It was so early in the morning that there wasn’t much to choose from — lots of old sitcom reruns, infomercials, and early-morning news broadcasts. He only paused his channel surfing when the sound of a familiar name reached his ears.

“Two-time Super Bowl MVP Landon Littlehale has announced a major partnership with Play with Pride, a nonprofit organization promoting inclusion for LGBTQ athletes in school sports.”

Asher smiled warmly as the anchor went on to describe the scholarship program Landon was helping to develop. It was crazy to think that one of the wealthiest and most famous athletes in the entire country had once been embarrassed at his family’s middle-class home. Things sure do change, don’t they?

“The Brindleton Bay Bobcats quarterback was recently photographed sharing an intimate dinner with Italian model Giovanni Morelli, though representatives have yet to confirm the relationship.”

With a heavy sigh, Asher turned off the TV. It had been nearly five years since he’d last heard from Landon, though it was easy to keep up with him, given he was now living in the public eye. And Asher was happy for him…

But it was hard not to feel a little jealous too. Landon was off winning Super Bowls and dating Italian models; Ollie was a husband, a father, and a lawyer at a successful firm; Lily was happily married and loving her job as a researcher for a genetics lab… 

And then there was him. 

His salary was amazing, most of his coworkers were pretty cool, and he loved helping people, sure. But none of that really felt like it mattered compared to the emotional stress of losing patients, the exhaustion of working night shifts, the endless struggle of looking for a relationship, the frustration of living with his little sister, and now, the humiliation of being forced to sleep on his best friend’s couch.

Asher used to think there was no such thing as happy endings… 

But maybe they just existed for everyone else but him.


29 thoughts on “9.36: Happy Endings

    1. Ha!!! Get your mind out of the gutter! 😂 (Great double meaning though… lol I never even thought of that 😂)

      Asher can’t hear you over his moping 😛 But maybe it will! 🤞🏻

      Liked by 2 people

  1. I love adult Asher’s new look. It works for him. I would think he wouldn’t have any trouble finding someone. But I guess being a doctor is rough, especially in the beginning and being a gay cuts down on the pool of potentials. Especially with no time to relationship shop. Unlike Penny. 🙄. Well, hopefully he can kick her out or at least set some ground rules if he’s insistent on helping her out. I suppose she might have changed over the past 10 or 12 years. Or not.

    Liked by 2 people

    1. He definitely grew into his looks 😉 But yeah, on a doctor’s schedule it’s really really hard to find time to date! Penny is having no trouble though 😂

      He definitely has to set boundaries instead of letting her mooch off him forever! We will get to see more of Penny very soon. She has definitely changed for the better in some ways… but not in others 😬

      Liked by 2 people

  2. sigh …was hoping he had a more positive attitude as an adult. I hope he realizes he’s enabling is sister instead of helping her…it’s a nasty habit to get into. He really needs to practice “tough” love on Penny. It’s neat to see//hear about LIlly, Ollie, and Landon’s adult lives as well. I’m dying though as I remember hitting 30 myself..the yr. I had my last born and quit smoking ..and gained massive weight….but wait till they are 40 lol…the struggle is real. Can’t wait to see where this story goes.

    PS I hope that online school is going well for you. Three more weeks here in SE corner of Kansas. I have students that basically have given up on school for now 😦

    Liked by 1 person

    1. Poor dude is forever a pessimist 😂 And yeah, I think subconsciously he knows, he just has a hard time feeling like he HAS to help her out of duty. Perhaps you’re right and a little tough love is in order!

      Everyone from Asher’s teen years are doing very well! It was fun to update them on everyone! And yeah, thirty is interesting 😂 I will be 31 next month so I was inspired by my own feelings over the past year! Haha

      And thank you! It’s going pretty good. I have like 50% of my students actually doing work for me? 😂 So i definitely have some who are checked out too! Hope you’re doing well otherwise!


  3. The more things change, the more they stay the same! Asher might have a successful career but still can’t get along with his sister!

    It was really great getting a glimpse into everyone’s life! It was especially cool to see Landon is going so well. I’m so happy he gets to live as the truest version of himself. And I’m really excited to see how this arc plays out!

    Liked by 1 person

    1. Hahaha that is so true — some things will stay the same no matter what, it seems!

      Glad you enjoyed this life update! Landon is doing fantastic! Living his dream as a star quarterback, open about his sexuality (a big deal for him, especially being in the public eye!), and using some of his fortune to give back to kids like him who might be struggling ❤️ (I’m very proud of Landon, can you tell? 😂)

      Glad you’re excited for what’s ahead! Me too! 😁 Thank you so much for reading ❤️❤️❤️


  4. Anti Shipper: Aw Pessimist Asher is best Asher! Glad he’s not trying to hop in bed with anybody just cause everybody around him seems so happy! Chin up Ash the worst of it is still to come!😇

    Dark WitcHazard: Hell No! I don’t care if she’s homeless living on the street pack her shit and tell her to get the hell out! This is your house she is the guess if she wants a place she can go be a struggling actress and not afford it elsewhere! Might see her on a corner sounds like she should at least get paid for all this sex she’s having and giving you a pimp fee for providing the location!

    Lover WitcHazard; I appreciate Asher’s sentiment but Lily is right you can’t just let her walk all over you cause her situation is bad. I hope she at least will repay the favor later on.

    Shipper WitcHazard: Aw I’m happy for Ollie I don’t do splitting up families unless it makes sense but with the kid I’m onboard for friendship with Ollie! As for Landon well he’s seems to be in a somewhat committed relationship so I’m not busting that up either. Glad Lily found her special person she definitely deserves it after everything she’s been through! Citizen how dare you talk about this new love interest Matt and having us wait a whole week for the goods!😝

    Liked by 1 person

    1. How did I know Anti would approve of things? 😂 Dark has some messed up ideas over there… though I’d agree with Lover that Asher is being too nice to his sister!

      Shipper is taking the current state of things with Landon and Ollie pretty well! Haha but, uh, sorry to disappoint but Matt actually isn’t in the next chapter, so we won’t see him for TWO weeks… 😬 *hides from Shipper’s wrath)


  5. Glad to see them all (short of Penny) doing well. Less glad to see Ash grow into his gloominess but hey, he can still get over it. He’s a young man, even if he’s getting grumpy 😀 and needs more sleep. Something tells me it’s gonna get worse for him before it gets better, though. : >

    Liked by 1 person

    1. Yup, everyone is doing great minus Penny 😂 And Asher is doing better than he thinks… like you said, he just kinda grew into that gloomy outlook, unfortunately 😬

      Worse before it gets better, huh? 🤔Well… isn’t that the definition of Rosebrook life? 😂


  6. It’s great to see that Ollie, Lily,and Landon all seem to have found where they belong in life, but Asher’s still alone. I hope he ends up with a happy life, too D: Maybe he can take in any kids Penny has from one of those flings. She doesn’t seem capable of raising a child at the moment. Asher needs to tough up and tell her to help out or get out! Perhaps she’ll get the message soon.

    Online school’s been pretty chaotic. As a student, almost every teacher’s been compelled to assign homework daily to confirm that I’m still alive. I can’t begin to imagine how crazy it is to be the teacher grading those assignments. At least the school year’s almost over!

    As always, I hope you have a great day!

    Liked by 1 person

    1. Rosebrooks *usually* find some happiness eventually, so… 🤞🏻🤞🏻 Ans haha hopefully Penny won’t wind up pregnant! Or you’re right, Asher would probably end up helping with that too 😬

      I bet it’s been crazy for you doing online school! Definitely crazy on the teaching end too… Let’s hope things can be back to normal next year 🤞🏻

      Thank you so much for reading (and being so kind too!) ❤️


  7. Ooh I love these little retrospective catch-ups! I’m so glad that Lily, Landon, and Ollie are all happy and successful. As for Asher… well, at least he’s got the successful part down? Lol 😂

    I can definitely see things going south with Penny very quickly if Asher still has the same temper he did in high school. It’s no wonder their relationship has declined since she moved in!

    I can’t wait to meet this Matt character and see more of Asher’s adult life! I’m loving it so far!

    Liked by 1 person

    1. I’m glad you enjoyed! This chapter is one of my personal faves of the gen. I love catching people up hehe And yes! Everyone (minus Penny) is successful and, well, MOST of them seem pretty happy too 😛

      Spoiler alert butttttt next chapter see will actually get to see him talk to Penny! So we’ll see if both of them are able to interact any more calmly as adults than they did as teens 😬

      Thank you again for your great comment! Glad you enjoyed 😁

      Liked by 1 person

  8. Loved catching up with everyone!

    Ohhhh…Ollie is a father and married with kid?? 👀👀👀 Well, at least he’s happy.

    And Landon is daring models…living the high life.

    Asher doesn’t realize he has it good too. He just hasn’t met Mr. Right. Maybe he’ll get a few tickets to a Super Bowl and an invite to a posh party? Lol! 😜

    I see Penny hasn’t changed and poor thing didn’t realize her dreams. Kind of sad. Glad Asher is being a good big bro. I do think he needs to set boundaries especially for his sanity! 😝😝😝

    Liked by 1 person

    1. Yeah, they all ended up in some pretty interesting places, huh? 😱 Successful careers and what seems to be successful families/relationships too! And you’re right — Asher doesn’t realize how good he has it too! And ha! I wonder how Asher would feel about a Super Bowl invite, hmm 🤔

      And you’re right, as easy as it is for us to be annoyed at Penny’s continued antics… it’s sad too. Asher says happy endings exist for everyone else but him, and yet his “ending” (spoiler alert, Asher — this ain’t the end for you yet😜) is a lot happier than his sister’s….

      Liked by 1 person

    1. That is a deliciously evil theory haha And quite possible! You never know… Still lots of Gen ahead 😉

      As always, thanks for reading (and sharing your fun prediction hehe)


    1. Hahahaha I mayyyyy have thought of you when I picked that country 😂 And yeah, they really do! (Especially for Lily’s husband, being on the west coast. 9 hours behind Switzerland = conference call at like 6am 😂)


  9. How old is Penny, exactly? Isn’t she two or three years younger then him, which means she would be either 27 or 28 by now. Jeez, she really needs to develop maturity. Asher can’t keep just putting her in when she needs him, she needs to learn how to deal with her own stuff. And the both of them just screaming at each other is not a good sign. It really shows how both sides got things to deal with.

    If I’d guess, it could also have to do with plain ol’ jealousy. From the looks of it, Penny feels humiliated as her actress dreams haven’t come true, she’s grinding to get money, while her ”genius” brother has a stable job and income.

    Still, she should have the minimum decency to treat him well. He’s letting her stay at his house for free, *and* even forcing him to have to sleep someone else bc she keeps bringing guys in. I agree with Lily, maybe if he puts his foot down, she’ll have to grown up. Some people just learn it the hard way, unfortunatly.

    I’d guess Asher would still be a pessimist. He was like that from the start, and when you start paying taxes things just go downhill lol.

    The whole doctor thing just remined me of a saying i heard once, that pretty much said the doctor’s family enjoy his money much more then he does, bc he’s always working a lot, so it’s up to his partner and childs to spend that Money.Ooof.Real mean saying i know lol

    Liked by 1 person

    1. Haha yes, Penny is a very immature 28 year old! And you might be right about jealousy playing a role… Penny never went to college (nothing wrong with that!) but this means she has spent the past 10 years of her life working part time jobs and trying to get her acting break (we will find out in future chapters just now successful… or not… that has been 😂). Meanwhile Asher definitely has it together! Steady job, lots of income, owns a house… You’re right that she’s being extremely inconsiderate right now 😬 And Asher is kind of letting her 😱

      And LOL it’s so true — adulthood is the ultimate thing to bring out the pessimism huh? 😂 And I think that quote about doctors is very true… Doctor schedules suck, especially doing what Asher does! Poor dude.

      Liked by 1 person

    1. Oh thank you!!!! I really appreciate you taking the time to read ❤️And I’m glad you love Asher! His gen has been so fun for me! Thanks again!!!!


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