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Dorothy Holdings fell in love with Stanley Uris when she was 13 years old. Luckily for her, the feelings were reciprocated. When she moved to Derry to live with her grandmother, she had no friends, that is until she met Richie “Trashmouth” Tozier. Richie introduced Dorothy to the other losers - at the time, being Stanley, Bill, and Eddie. The five of them clicked instantly, but Dorothy and Stanley were much closer than she was with anyone else. The two soft-spoken teenagers felt truly content around each other and stuck to each other like glue. The group of friends teased the two constantly, but when you are so in love, like they were, the teasing was easily ignored. It wasn’t until after their defeat of Pennywise that Stanley asked Dorothy to be his girlfriend...and the rest was history.


Derry, Maine - 1993


They had been having this fight for weeks now. Leading up to graduation, Stan had been constantly pressuring Dorothy about moving with him to Georgia - that they needed to get out of Derry for good. While he wasn’t wrong, she simply couldn’t. She couldn’t leave her grandmother alone to move down to Georgia with Stan. 


The cycle of fighting had truly become exhausting for Dorothy. Their relationship had a painful strain on it due to the constant arguing and if Dorothy was being completely honest with herself, she wasn’t happy anymore with Stan.


Today was no different. Her grandmother was at church helping with the sisterhood, leaving the young couple alone at the house. The summer heat was high that day, causing the two to be even more irritable than usual. The two were stretched out on the couch, Stan lazily watching the television while Dorothy read one of her magazines. A sigh came from Stan, making Dorothy set her magazine down and stare ahead of her at him,


“What’s wrong?” Dorothy asked, sitting up slightly, although, she already knew what the answer was.


She moved Stan’s feet onto her lap while she adjusted herself and sat back on the couch, her hands resting on his ankles. She didn’t want to have this conversation again, but she knew that Stan wouldn’t quit until she came with him.


Stanley, being the stubborn sweetheart he was, sat up and rested his hands on top of Dorothy’s, the television being tuned out now by the both of them, 


“Come with me to Georgia...please,” He begged, causing Dorothy to instantly gape her mouth open and lean away, only to be pulled back by Stan, gently of course, “I know you don’t want to leave your grandmother, but you aren’t going to go anywhere here. You know that, right? Nothing is here for y-”


“Stanley, I don’t want to go with you! I-I can’t!” She began, tears swelling in her eyes as she shot up off the couch suddenly, her hands growing clammy as she cracked her knuckles, running her shaky hands through her long, honey butter, blonde hair.


Turning around, Dorothy stared at Stan who was clearly frazzled. His eyebrows were furrowed as he stared at the coffee table, trying his best not to cry...cheeks red with embarrassment. Her heart sank at the sight of him, knowing that he only wanted what was best for her - but she was scared, she couldn’t go.


“But why....why? I thought you wanted to! I thought you wanted to get out of here and be happy! Together!” Stan suddenly burst, breaking the thick tension in the room, looking up at Dorothy, eyes glazed over from tears.


Shaking her head, Dorothy’s shoulders sank as she crossed her arms over her chest, closing her eyes so she, too, wouldn’t cry,


“You’ve been so overbearing lately...with this whole idea of going down south. I know it’s what you want, but me? It’s not what I want, Stan. My grandmother is getting older, she’s the only family I have, I can’t just leave her. She needs me he-”


“What about me? I’m your family...your boyfriend! Do I not matter to you anymore-”


“You know that is not true!” Dorothy exclaimed, voice ringing throughout the house.


The room fell silent, both sides of the party unsure as to what they wanted to say or should say next. It was Stan, however, who spoke first,


“Do you still love me?” He asked, causing Dorothy’s heart to sting with pain.


“Of course I do Stan, but we are only 18...I’m not ready to leave yet. I’m not ready to run away with you on our own...I’m not going to just abandon my grandmother so you can chase your dreams. There are plenty of schools around Derry that you can study Accounting at! I am all for you chasing your dreams, but...this dream just doesn’t have me in it.” 


That was what snapped Stanley into reality. This wasn’t a fantasy anymore, this was the real deal. They were adults and not kids anymore.


“So this is it? I take it this is fucking it.” Stan suddenly grumbled, pushing himself off the old couch before going to put his shoes on to go.

“W-What are you doing?” Dorothy asked, watching in confusion as he gathered around to leave. What did he mean by this was it?


“It’s obvious, Dory! It’s obvious that you don’t wanna go, that you don’t want to be with me! I just, I just don’t understand why you had to lead me on this past year...I really,” A sigh came from Stanley’s lips before he continued, “I really thought that you wanted to come.” He admitted, shoes on and back facing the front door.


Pursing her lips, Dorothy shook her head,


“I’m sorry Stan...I just can’t...I’m not ready.” She whispered, tears now rolling down her pale cheeks, eyes and nose growing red.


There was no proper goodbye between the two. Stanley left shortly after and that was the last time Dorothy had seen him. Their breakup, their shitty goodbye, it was the worst pain Dorothy ever had to endure. 


Lambertville, Michigan - 2016


41 years old and she had nothing going for her.


Dorothy was a gas station attendant at a truck stop working over 40 hours a week, yet still not bringing home anything to live off of. To say her life went downhill was an understatement, life gave her both middle fingers and kicked her to the curb.


After her breakup with Stan, she moved to Michigan a few years later. In 2000, her grandmother passed away. Dorothy’s worst secret was that she didn’t go back home for the funeral. Her grandmother was the only person in her life, and vice versa, and she didn’t show up. She kicked herself for that mistake, and eventually spiraled into a mess of drinking and constant fuck ups that led her into rehab. Thankfully, she recovered and is doing better - but life was still shit.


The half an hour walk back home after a long shift was probably the worst part about it all. She was constantly sore and it seemed no matter how much she slept, she was still in pain.


Dragging her feet along the rubble of the damaged road, Dorothy tiredly made her way down the long stretch of road back to her apartment. How did her life end up like this? So... fucked? She told herself numerous times that she would never end up like her mother, yet here she was.


The sudden obnoxious ringing of her cell phone ripped her from her thoughts. Rummaging through her purse, Dorothy pulled out her cell phone, flipped the top open before pressing the phone to her ear,


“Dorothy Holdings.” She answered, voice calm as she continued back down the road. She wasn’t expecting a call from her therapist, and there wasn’t a home search scheduled yet, so who was calling?


“Still kept the last name...figured you and Stan would have gotten hitched by now.” The voice on the other end joked.


The familiar name caused Dorothy to stop dead in her tracks. She hadn’t heard, nor thought, that name since the 90s.


“H-How...who is this?” She suddenly demanded, anger bubbling inside her stomach.


“Woah, Dorothy, it’s me...Mike. Mike Hanlon, from Derry.” Mike laughed a little, the awkward tension filling the phone call.


“Mike, hey, wow, I’m sorry. I haven’’s been a long time.” Dorothy apologized, sitting on the curb now, purse in between her legs, elbows resting on her knees.


“27 remember what we promised all those years ago?”


“N-No...I don’t remember much, Mike. I barely remember you…-”


“Dorothy...It’s back.”