A Very Merry Proposal

An Annie Fan Fiction

This story is centered around Roland Sheffield and how he eventually decides to propose to Molly Warbucks. It is set during Thanksgiving. & Christmas time of their sophomore year of college. Enjoy! I own no characters from either Annie or Meet Me In St Louis. Roland and all his family members are my own creation.

Thank you to Erica Richards and Naomi Cohen for character names suggestions for the children of Esther and Lon's children. I would guess that since Agnes and Tootie were the youngest of the bunch (12 and 5 in the movie Meet Me In St Louis) they would not have kids yet but could be possibly be married or engaged by this point.

Esther has two children Millie who is 17 and Chip who is 11 and Lon has one son Alonzo the Third who is 14. Esther is married to John Truitt and Lon is married to Lucille Ballard (the girl who is in the dance scene where Banjos is sung in the musical)

During the time Roland Sheffield was in the hospital recovering from his car accident he realized one thing. That one thing was that he loved Molly Warbucks and wanted to spend the rest of his life with her. There was a lot to consider for someone who was nineteen years old but he knew deep down inside that Molly was the girl he would love for the rest of his life.

After he was released his mother took him home to New York to recover. He would miss the rest of semester and take his coursework with him to complete and mail it back to the school.

"Mom, you like Molly don't you?" he asked his mother one afternoon.

Carolyn Sheffield nodded. " She's always been a bit shy but I've grown very fond of her. Annemaire only has you don't you know? She never had a sister."

Roland smiled. "I want to marry her Mom."

Carolyn Sheffield's eyes lit up in delight. "Oh sweetheart, what wonderful news! I am so excited that you're ready to take the next step in your relationship. When do you think you might propose to her?"

Roland cleared his throat. "Christmas break. I really don't want to put it off."

Carolyn Sheffield smiled to herself. "I'm sure your grandparents will have a great story to tell you about how they got engaged... they got engaged on Christmas Day thirty eight years ago. I always love hearing that story."

"They're coming over for Thanksgiving right?"

Carolyn shook her head. "Actually we are going to the Hamptons. Grandma Rose's family is flying in from St Louis. It's not often we get to see them you know. You'll get to see all your second cousins."

"Is their Irish maid coming too? I've always heard amazing things about her hickory nut cake from Grandma Rose."

"Katie's been dead for about ten years but Great Aunt Esther took over making it.. it's always such a delicious cake."

On Thanksgiving the Sheffield's arrived in the Hamptons at around noon. Dinner was to start at two thirty. Rose Sheffield opened the door. "Hello darlings, come in Warren went to the airport to pick my siblings up and they should be back soon. Help yourself to some appetizers. Roland, dear how have you been doing with your recovery from your accident?"

"Healing up nicely Grandma. I am finishing all my course work at home for the rest of the semester so that way I can be top of everything for the spring. I am actually hoping to graduate a year early."

Rose kissed her grandson on the forehead softly. "You work so hard, we've always been so proud of you and your sister. "

"Grandma. guess what? Roland said he's going to ask Molly Warbucks to marry him. I am so excited to have an older sister!" Annemarie jumped up and down with excitement.

Rose Sheffield's eyes lit up. "Oh, how excellent! Everyone else will be so excited to hear this news. Molly is one of the sweetest girls I have ever met."

Carolyn smiled at her mother in law.. "One thing I think all of us should be grateful for is that her cousin introduced them to each other their sophomore year of high school. You remember the first time you met Molly don't you Rose?"

Rose nodded. "Of course I do. Do Molly's parents know anything about the engagement yet?"

Carolyn shook her head. "No, I think Roland would like to surprise Molly on Christmas Eve and propose to her then."

""You're very much like your grandfather indeed." Rose said.

"How did he propose to you Grandma?" Annemarie asked.

"Well, we were dating long distance for several months. I think he was a bit anxious and tired of waiting and at the time my father's job was going to transfer him to New York."

"Did he know about Great Grandfather's job transfer?" Annemarie asked.

Rose nodded. " I had written him a letter the minute I heard about and told him there may be a possibility we might move to New York but we weren't sure of the details yet of the exact date we were going to move."

"Did you end up moving?"

Rose shook her head. "No, we ended up staying in St. Louis and not moving away.

Annemarie's face crinkled in confusion. "Well, how does Grandfather's proposal play into it then?"

Rose smiled at the memory. "I think he was honestly a little frustrated that I had been dragging my feet for so long. Therefore on Christmas Day he came over to my parent's house catching all of us a bit of guard and saying "Rose Smith, I can't wait any longer. I want to marry you.. Merry Christmas.. And the rest so they say is history."

Five minutes later a car door slammed/\

"Why don't you two go help your aunts and uncles carry their bags and dishes in?"

"Sure thing Grandma." Annemarie said

When Annemarie and Roland got outside their Aunt Esther smiled at them

"Darlings, just look at you and how you've grown!"

Annemarie kissed her great-aunt's cheek " Hi Aunt Esther. It's great to see you guys too. We wish that we saw you guys more often. I'll take that platter from you!"

Esther's son Chip gave Roland a high five. "Hey RJ. What's new with you?"

Roland smiled. " I have news to tell you guys.. I'm gonna let everyone get settled first. and once we all sit down I'll tell you."

His grandfather patted his shoulder. "How are you healing up from your accident my boy?"

"Slowly but surely Grandpa. Hopefully I'll be fully recovered by the middle part of next month."

"Your studies aren't affected too much are they?"

Roland shook his head. "Nope, Mom worked things out with my professors so I get all my class work mailed to me. I try to complete one assignment for each class a day."

""That's my boy!"

Once the whole family was settled down at the dinner table Carolyn tapped her wine glass. "Roland has wonderful news to share with all of you."

"What is it? his aunt Agnes asked.

"Well, I've told you all about my girlfriend Molly right?"

His family nodded.

"I'm going to ask her to marry me."

Hoots and hollers rang out around the table.

"Who's this lucky girl and when are we going to meet her? We've always heard you talk about her." his cousin Lon asked him.

" Her name is Molly and we've known each other since tenth grade. You guys are here for a week... I'll try to get her to come up here to visit. She'd love to meet you all."

"RJ, when are you going to propose to her?".. his cousin Lon asked

"Christmas break...maybe on Christmas Eve."

Esther looked at her husband John lovingly. "Do you remember when you proposed to me?""

"I sure do. That was a great night."

When they got home from their grandmother's house Roland called the Warbucks house

"Good Evening Warbucks Residence, Grace speaking."

"Hi Mrs. Warbucks, it's Roland."

Roland could feel the warmth of his girlfriend's mother's smile through the phone line. "Hello sweetheart, how was your Thanksgiving? I was just thinking of giving your mother a call."

"Great, Mrs. Warbucks! Can I talk to Molly?"

"Of course, hold on a moment. Let me get her."

"Five minutes later Molly picked up the phone."

"Hi R.J."

"Hey Mol, what are you doing this weekend?"

"Not a lot why?"

"Well my relatives from St. Louis are visiting and they wanted to meet you. My grandparents were wondering if you wanted to come to the Hamptons for a few days.. when you do go back to Buffalo?"

Molly was quiet.


"I have a class at 9:30 am on Monday morning so I need to back in my dorm by 6:00pm on Sunday."

"Okay, there's a train station not far from my grandparent's house so you can sleep over on Saturday night and he'll take you there in the morning."

"Okay, my mom can drop me off at your house on Saturday morning. I can't wait to meet your family!"

"They can't wait to meet you either."

"When does your semester end?" Molly asked.

"The 18th. What about you?"

"Same time. Do you want to spend time together before all the holiday craziness starts or do you leave for Lake Placid right away when school gets out?"

Molly was quiet again.

"We don't leave for Lake Placid until Dec 26th and have our vacation booked until January 2nd. You're always welcome to join us you know, Your parents and Annemarie can come too."

"I'll let them know. See you Saturday morning at around 10:00am.

"Okay, my mom wants to talk to your mom."


Saturday morning Grace dropped off Molly at 10 am sharp.

"Hello Carolyn, thanks for offering to take Molly to the train station tomorrow. Would you all like to come over on Christmas Eve? My sisters are going to the in laws this year."

Carolyn Sheffield smiled and winked at her son. "Perfect, what time should we come?

" Dinner will be at 6:00pm but we'll have appetizers at around 4:30."

Annemarie ran down the front steps. "Hi Molly, I just hung up with my grandma! My aunts and uncles are so excited to meet you. R.J is waiting for you inside, come on!

Molly kissed her mother's check softly. "See you in few weeks Mama."

"Good luck with your exams sweetheart. We'll see you soon."

Once Molly was inside the house and out of earshot Carolyn leaned into passenger's side window. "I don't know if Roland will like that i'm telling you this as I think he wants to surprise Molly but wedding bells are in the near future for our children."

Grace's eyes grew wide. "Really, he's going to propose to her?

"Christmas Eve."

"If I dare say so myself... it's about time. I am surprised that they didn't get engaged in the summer." Grace said.

"This is so exciting Grace! We're thrilled to be joining your family. Roland is taking her to my in laws this weekend to meet Rose's family this weekend... they are excited to meet her."

"We'd love to invite you all to Lake Placid this year... my family would love to meet the rest of yours."

"When is the vacation booked for?"

"December 26th-January 2nd. It will be a prefect way to celebrate the engagement. When do you suppose they'll get married?"

Carolyn grinned. I don't think we wants to wait that long so I won't be surprised if the wedding will be during spring break or as soon as school gets out for the year. Do you think Molly would want to transfer schools so she could be closer to Roland?"

"Honestly, I think that's what she's wanted all along."

Soon after Grace pulled out of the driveway Roland and Molly threw their bags into Roland's truck and headed for the Hamptons.

" I am so excited to meet your family and see your grandfather's house. This is my first time going there."

Roland smiled. "My grandparents can't wait to see you again and the rest of my family can't wait to meet you either."

"R.J. I really wish we didn't go to school so far a part. I miss you so much."

Roland winked at her. "That will change sooner than you think Mol!"

Molly shot her former boyfriend a confused glance. "You're not transferring to Buffalo are you?"

Roland shook his head. "I will have the best surprise for your over Christmas break. You'll just have to wait and see what it is. "

Molly could not be more confused. "Okay, whatever you say."

When he pulled in the driveway of his grandparent's house Rose came out on the porch.

"Hello Molly, it's so wonderful to see you again.

Molly hugged her boyfriend's grandmother tightly. "Hi Mrs. Sheffield, it's good to see you again too. It's been so long."

"I know darling. Please call me Rose. You've been part of this family long enough you're practically one of us."

"Roland, show Molly to her room please. Everyone else is just about ready for lunch."

Roland nodded "Okay, Grandma!"

Once Molly took her seat at the table in the dining room Warren Sheffield smiled at her.

"Molly, how was your fall semester? Still doing playing field hockey and doing plays?"

Molly grinned. "Yes, Mr. Sheffield… er I mean Warren. We had a great season for Field Hockey. We went to the quarterfinals in the state tournament. I'll be trying out for the winter play when I get back to school in January."

"Do you have any brothers or sisters Molly?" Esther asked

Molly swallowed a bite of her sandwich. "My older sister Annie and I are adopted. She's four years older than me and recently got engaged. I am so excited for her wedding! It's going to be in the spring!"

"How old is Annie?"

"She just turned 23 in October. We have a younger brother & sister who just turned 10. They're twins and in fifth grade"

"What are their names"

"Joanne and Frederick."

"We can't wait to meet them."

"Molly, Carolyn called before you came and invited us to Lake Placid for Christmas week. We look forward to joining you." Rose said.

Molly's eyes lit up. "Really? That's great! I can't wait for you guys to meet the rest of my family. We always have a huge family reunion every year."

"What are you majoring in Molly?" asked Millie.

"I just declared my major. I am studying Early Childhood Education and Special Education."

Rose's eyes lit up. "How wonderful. What made you decide on Special Education?"

"Well, I was diagnosed with dyslexia soon after my parents adopted me and I overcame so many challenges to get to where I am today I want to help children with disabilities overcome their challenges. I had so many teachers along the way that were always so encouraging."

Lucille's eyes misted over. "You're so inspiring."

Molly blushed. "Thank you." She whispered.

Rose smiled at Molly. "You've always been modest when you don't need to be. Lucille's right you know."

Later that night as she was getting ready for bed Rose knocked on Molly's door.

"Do you have everything you need Molly?"

Molly nodded. " Thank you for offering to drive me to the train station tomorrow."

"It's not a problem."

"Roland was acting strange when we were driving up here. Do you know what's going on Rose?"

Rose was taken aback. "He has a very special surprise for you on Christmas Eve dear. I don't want to spoil it."

"But when I asked him if he wanted to transfer to Buffalo he looked at me like I had two heads. Doesn't he want to live to closer to me? He knows how much I miss him."

Rose patted Molly's shoulder. "Of course he does and he misses you too. He's constantly tells Warren and I how much he cares about you. Annemarie told me at Thanksgiving that she always thought you were an older sister to her."

Molly smiled. "She's like a sister to me too. Then she was quiet for about ten minutes

"What's wrong sweetheart?"

Molly sighed. "It's just that I've never met another boy quite like Roland and I don't think I ever will. It's been hard letting go of our relationship."

"You won't have to worry about that anymore."

"What do you mean?"

Rose smiled. "As I said I don't want to spoil Roland's surprise. You'll have to wait until Christmas Eve."

Molly sighed realizing that this conversation would get her nowhere quite fast. "Alright."

Rose kissed Molly's forehead. "Good night my sweet Molly. Warren and I love you very dearly you know."

Molly gave Roland's grandmother a tight squeeze. "I love you too Rose. Good night."

Molly waited for anticipation for Christmas Eve to come and counted down the days until she would find out what Roland's special surprise was. After her last final her aunt Anne picked her and Isabella up.

" Molly, sweetheart I heard Roland has a special surprise for you for Christmas. What do you think it is? Her aunt asked her.

Molly shrugged. " I haven't got a clue. He was acting so weird before we back to school at the end of Thanksgiving break. I've been kind of anxious about ever since."

Isabella's eyes grew wide. "You don't think he's going to propose to you do you?"

Molly shot a side long glance at her cousin who had been the person who had matched them up four years before. "He hasn't said anything to you has he Bel?"

Isabella shook her head. "Even if he did I wouldn't tell you. You know that I am great at keeping secrets."

"Well, that sure doesn't help me."

Isabella gazed out the window. She really hoped that Roland was going to propose to Molly on Christmas Eve. Then there would be two weddings in the Warbucks family to plan.

On Christmas Eve the doorbell rang at 4:30. "Molly, sweetheart can you get the door?" Grace asked

"Sure Mama."

When Molly opened the door she greeted the Sheffields warmly.

"Hey, guys, I'll take your coats upstairs and put them in the guest room. We're just about ready to have appetizers." Molly smiled.

"I'll come with you." Roland offered.

Molly shrugged. "Okay. If you really want to. I'll be back down in about three minutes."

"That's okay, I really need to talk to you. It's important."

'Great, then we can get down to the reason why you've been acting so strange.' Molly thought to herself. "Okay, come on let's go." She replied.

Once they got up to the guest room Roland shut the door behind them.

"Why are you acting so strange Roland and what's that special surprise your grandmother was telling me about that she didn't have any intention of spoiling?"

"Well, you've always wanted to be closer to each other right?"

Molly nodded. "Yes, I do. It's been so hard going to school so far away from you."

"Well, you'll only have one more semester at Buffalo and then you'll be closer to me."

Molly stared at Roland. "What do you mean Roland? You're driving me crazy!"

"And I think we can both agree we've been going crazy without each other."

Molly nodded." That's for darn sure! Can you just get this over with and tell me what on earth is going on? This whole being secretive thing is not like you at all Roland!" she shot Roland a fiery glance and tears sprang to her eyes She turned away from him.

"Molly Jane look at me." Roland whispered.

Molly turned around and noticed that Roland was on one knee.

"Will you marry me Molly Warbucks?"

Molly was taken aback "Roland….."

"Well, don't keep me waiting."

Molly's anger melted away and she threw her arms around her fiancé

"Yes, my answer is yes. Of course I'll marry you!"

Roland slowly slipped a ring on Molly's finger. " I love you Molly and I will love you forever."

"I love you too." Molly whispered.

Molly pulled back from the embrace. "What exactly did you mean when you said last semester will be my last at Buffalo?"

"Well, the other part of my surprise is that my grandfather has been working with your father and your Aunt Jen to get us an apartment in Cambridge. You'll be transferring to Lesley College next fall. We'll be moving into the apartment at the end of the semester."

"When should we get married?"

"That will be tricky since I hear Annie is planning on getting married next summer."

Molly grinned. " I can talk to her and I'm sure we can figure something out. Knowing my family we'll have sort of big party to celebrate both weddings. We've had combined graduation parties before… this won't be much different."

"Aren't you going to study abroad next fall?" Roland asked.

Molly shrugged. "I was going to but if we're going to be planning a wedding I can always wait until senior year to go. I can always leave for study abroad before school starts so we can do a honeymoon before all my classes start."