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Matchmaking Royalty

Summary:

In The Enchanted Forest, a teenage Regina is set up by a mysterious matchmaker with interesting results.

Notes:

This story was originally posted on fanfiction.net in like 2016? I ended up deleting it because I always felt like the idea had more potential than what I eventually wrote. Recently I almost lost the file and I decided I would rather have it posted for people to (hopefully) enjoy than just be lost. I'm only doing some light edits so the chapters will be posted quickly.

Chapter 1: Regina and the Matchmaker

Chapter Text

"How about him?"

Regina barely glanced at the brutish man in the sketch before shaking her head in the negative. They had already been at this for three hours and -much to her mother’s dismay- she was no closer to finding a husband than she was when they started. 

She wasn't being purposefully difficult. She really wasn't. She knows that this is quite literally what she was bred for. And yet, she can't find it in herself to be excited. She is happy that her mother is letting her have any say at all in the person she marries. Despite the gratitude, here she is, halfheartedly perusing the book of eligible royalty that the Matchmaker had put in front of her. 

How am I supposed to judge someone by only a sketch and a small bio?

Yes, some were visibly handsome but what does that mean of their personalities? Of course, the Matchmaker and her mother are putting their two cents in as well but they only make her more confused. 

"Let me see if I can find someone." The matchmaker says and slides the binder away from her. 

He is younger than Regina assumed he would be when her mother first told her about the visit. She would guess he is about 45 but perhaps his serious expression make him look older. I wonder what made him go into this business? He's become quite successful for himself. Years ago delegates or the royal families themselves would make the matches for their children but somehow this wayward traveler with only his quill and a book of faces has convinced every family of status that they need his services. Her mother for one, would have been more than happy with finding Regina a husband on her own and has made that very clear. Yet, in fear that the other nobles would think her behind on the times (or even worse, think they can't afford his services) she decided to call upon this mysterious man himself. He is a very unassuming man though. Honestly the most intriguing thing about him in Regina's opinion is that he doesn't have a name. Or refuses to give it out. He simply goes by Matchmaker. As he quickly scans the pages Regina's eyes wander to the portrait sketches on each page. 

"Who is that?" She suddenly and reaches out to stop the page from flipping before she can even question her actions. 

"Oh, this section of the book is of eligible females. You'll be added in as well until you become betrothed." He says not really answering her question. 

Somewhere in the back of her mind Regina realizes that she is still holding down the page in the book, which is rather rude, but she can't seem to focus on anything but the portrait in front of her. 

There is a detailed sketch of a girl around Regina's own age. She is in what appears to be a very expensive gown, and yet, she's sitting on the grass between two flower beds. The girl's eyes are questioning and thoughtful. 

Finally Lady Cora leans over (as gracefully as possible) from her chair on the other side of the table so she is able to see the portrait that has entranced her daughter.  "That's Princess Emma." 

"Of the Enchanted Forrest Kingdom?" Regina finds her voice to ask. 

She thankfully has the forethought of mind to look her mother in the eye while speaking. 

"Yes." 

Regina knows of the princess and has even been to their kingdom once but she has never met her or seen a picture that wasn't of the other girl as a young child. 

"Is she not the crown princess? If she is next in line for the throne surely men would offer their hand to her without the need of a matchmaker?" Regina questions.

"She has had offers, of course." The Matchmaker replies but his tone suggests that there is more to the story than that. Regina is thankful that her mother is nosy and asks (demands) to know why the princess would be included in the book. "The princess is...strong-willed. I believe they have had trouble finding someone who will conceded to her and whom she likes." The Matchmaker says diplomatically. He then slides the book away from Regina and begins questioning her again about all matter of personality traits. 

Regina goes back to only half listening. She can't help but wonder why the princess is having so much trouble finding someone. She seems...so utterly perfect. Wouldn't being strong-willed be a good trait for a leader? Regina would be jealous of this girl if she weren’t so busy being awed by her. She finds herself hoping that the princess doesn't settle for anyone.

"Regina?" The man calls.

"Yes?" She shakes away her musings.

"How about him?" He slides the book over once more.

Prince Robin of Sherwood. A handsome man. The sketch shows him with his bow and arrow. 28 years old. Loves nature. Which is lucky for him considering more than half of that region is forest. Third in line for the throne. He will easily get bumped even further as soon as his oldest brother and wife have a child. But that shouldn't be too much of a deterrent for Mother considering a lot of the nobles in this book aren't even this close in line for the crown. The only other description is: Fighter for the common people. Whatever that means. Overall, he seems the most promising to Regina out of the ones they've singled out for her. Something still doesn't feel right though. 

"Maybe." She says.

She has only given one other maybe so far so the Matchmaker seems to take this as a success.

Lady Cora however, gives a displeased gruff before standing."Matchmaker, I believe it is time to retire for the night. Will you be staying with us?"

The Matchmaker hears the dismissal and stands as well. Regina with him, as a sign of respect. 

"If you would be so gracious as to offer a bed I would be most grateful." He says with a little bow. 

"Very good. Perhaps we will resume tomorrow. The maid will bring you to a free room and I'll have supper sent to you as well."

"Thank you my lady." He replies and goes to take his book before following the maid out.

"Will you leave the book for us?"

It's technically a question but Cora's voice brokers no objections. Still, the Matchmaker hesitates. The book is his livelihood. In the end he still leaves it on the table though. Lady Cora can be truly intimidating.

Once the man leaves the room, Lady Cora indicates that Regina should sit across from her once more. 

"You're making all of this much more difficult than it has to be Regina." Her mother scolds before opening the book.

Regina says nothing. She finds that this is often best. Even more so than apologizing. Silence fills the room for several minutes. The only sound is the soft rustling of the pages as Lady Cora determinedly flips through the book. Regina becomes anxious. She would rather her mother just yell at her now for being (apathetic? insolent? ungrateful?) than to drag out any sort of punishment. Finally Lady Cora stops at a page. Regina doesn't dare try to peak at which once. Her mother face goes through a range of emotions while reading. First it's a frown, then she smirks as if she's won a prize, then she squints her eyes and purses her lips before eventually looking up at her daughter. Lady Cora spins the book to face Regina and slides it across, saying nothing.

Regina doesn't look right away. She is almost scared to see whom her mother has singled out. When she does finally look, it's hard to keep the shock and confusion off her face.

"Princess Emma?" She questions while looking at the beautiful girl's portrait.

Lady Cora says nothing.

Regina reads the bio. Crown Princess Emma of the Enchanted Forrest Kingdom. First in line for her throne. 18 years old. One younger sibling, Neal, aged seven. Class A sword fighter. Beloved by all.

Very short. Its brevity only makes Regina more curious about who this girl really is. How does The Matchmaker not know more about such a public figure? 

"You want the princess and I..." Regina trails off not finding a good way to ask her question. Lady Cora seems to understand anyway.

"Yes."

"Is that done?" Her daughter questions. "How would there be an heir?" She gets a strange feeling in her stomach at the mention of making heirs with the princess.

"It's certainly not common, especially with direct royal families, but yes. And you should know that magic always finds a way Regina."

Regina is quiet for some time. She had never thought about another girl in that way. What would have been the point in allowing those thoughts when her mother had seemed so determined to marry her off to a prince her whole life? She still doesn't know what to think. Would a marriage between two women be very different than one between a man and woman?

Then she thinks about Princess Emma specifically. She had never before seen someone (in real life or a picture) and just wanted to get to know them so badly. And she feels that this princess is somehow a rare beauty that will tragically go unappreciated by her future husband.

"How would this work?" Regina finally asks. The more information she has the less daunting this decision will seem. "I assume she won't come here as other suitors have. Would I go visit the castle? Do we have to write to the King and Queen. If she says yes, what happens next? Do I court her? I don't know how to do that. And if we had children who would carry them?" She begins listing off all her confusion as it comes to her.

"Regina!" Her mother snaps.

"Sorry."

"What have I told you about apologizing so much?"

"That it makes me appear weak."

"Exactly" Lady Cora says with a huff. "Now, first of all, yes we would have to send a letter informing the King and Queen that you would like to meet their daughter in the hopes of courting her. If they agree to the visit they will give us a list of dates. If not, they will make a polite excuse to decline. Now, if you do end up going to the castle, you'd have to go alone. It wouldn't look good to bring a parent with you. Could I trust you to behave appropriately?"

"Yes, mother."

"Good. If the princess appears to be even a little interested, you will begin courting her. This includes visits, presents, letters, and perhaps public appearances. Everything else having to do with the relationship would be discussed after marriage."

"Okay."

"This is your choice then? You have to be certain. This is a gamble for us. If she rejects you or you decide at the last second that you cannot marry a woman it will be significantly more difficult to find you a suitable spouse." Lady Cora reminds her sternly.

Regina takes one last look at the picture in front of her and inhales deeply.

"Yes, this is my choice." She breathes out.

"Excellent." Her mother smiles for the first time all evening.