Prompt: How do they deal with Henry going to college? Or high school for that matter? Who is impossible at parent/teacher conferences?
"I'll be fine, Moms. You worry too much," Henry said while Regina and Emma squeezed him in one of their group hugs.
"We're your mothers. Of course we worry too much," Regina replied before both women reluctantly pulled away.
Henry smiled at them once his face wasn't buried in their hair. "You two raised me to make good choices and after everything we've faced together, how can you think me going away to college is scary?"
"It's not that we don't trust you, Henry," Emma said. "We do. We just don't trust other people."
"And this is your first time away from home. Well, without one of us being with you," Regina added.
"That's a good thing," Henry said and smiled a little wider. "I know I belong here. Storybrooke is my home. But…I want to have a life outside of here, at least for a little while. Emma got to do it, and my dad. Now it's my turn."
Regina smiled back at him, but her eyes were filled with tears that had yet to fall. "My little prince is all grown up."
"And coming home for my first visit in less than four months," he replied with a chuckle. "It'll be Thanksgiving before you know it, and then you'll blink and I'll be back again for Christmas. Besides, we all have phones. Magical, secret town in Maine or not, we'll text and call and video chat when we can or when we need to."
"It won't be the same," Regina confessed.
"But it's better than nothing, right," Henry asked them.
"Definitely," Emma answered.
"I promise I'll come home in one piece," Henry told them with a grin.
"That is not funny, Henry Daniel Mills," Regina scolded him. "Not after the amount of times we've almost lost you."
"Regina, relax. He'll call us if he's in any trouble," Emma said and then looked at Henry. "Right, Kid?"
"Yeah," he replied. "I love you, Moms."
"We love you, too," Regina said before both she and Emma pulled him into another hug.
"Um, you guys know you're coming with me to drop me off, right," Henry asked with a bit of a struggle as they nearly suffocated him.
"We need as much time for goodbyes as we can get," Regina said.
"Okay, but how about we save the real goodbyes when we're standing in my dorm," Henry requested. "Right now I just want to have one last family meal with my moms in the house I grew up in before we leave."
Always willing to give in to Henry and almost every single one of his whims, the three of them sat down for brunch in the Mills' family dining room. Snow and Charming arrived a little later than expected with Neal, but no one—not even Regina—complained. They were welcomed almost halfway through the meal and the six of them ate together until it was time to make the drive to New York.
Before they did that, his grandparents spoiled him with two hundred dollars tucked inside a "Congrats Grad" card along with a sentimental message about how they'd enjoyed watching him grow into the wise, brave and creative young man he was. It almost moved him to tears, but he was able to keep his emotions in check while Snow and Regina broke down and cried. Again.
Charming and Emma remained happy and proud while Regina and Snow had to pass tissues back and forth from the travel pack Regina specifically bought for when they left him at the school and she just couldn't contain her emotions any longer. It was a good thing Emma snuck another eight packages in their cart before they hit the checkout the day they bought them and other supplies, because they were going to need them. Regina and Emma gave him a joint gift of all the essential items he needed while he would be on his own, including a care package with chocolates and other junk food for him to enjoy while he was adjusting to life away at college.
As soon as gift giving was over, Snow and Charming said their goodbyes to Henry from the foyer. They stayed at the mansion with Neal and agreed to clean up the dishes from brunch while Emma and Regina drove him to the university. With one less thing for the two of them to worry about, they got into Regina's Mercedes and the three of them made their way out of town.
Regina was behind the wheel all the way to New York with Emma navigating from the passenger's seat. Henry sat in the back with a backpack full of books that he pulled out to read during the trip, which made him a very quiet and boring passenger. Emma didn't mind because she was too focused on trying to play her road trip music in a way that would allow the whole car to hear, but every few minutes Regina couldn't help but look into the rear view mirror to check on their son.
Finally, around dinner time, the family of three had arrived in New York. They stopped for dinner at a nice restaurant near the school while the sun was in the middle of its descent behind the horizon. During dinner, Emma gave Henry a rundown of how the subway and train station worked. Henry spent a majority of that time telling Emma he already knew because he'd lived their with her once before for an entire year. After the third time he'd mentioned that, Regina withdrew from the conversation.
Emma was the first to notice. As soon as she did, the blonde reached out under the table and placed a hand on her lower thigh. She squeezed just above Regina's knee while she listened to Henry go on and on about all the things he had scheduled after orientation the next day.
Regina turned and gave Emma a grateful smile, to which Emma responded with a smile of her own and a caring look in her warm eyes. Henry remained oblivious. Or at least, that was what Emma and Regina had believed until they said their final goodbyes at the dorm hall.
"I don't think I need to tell you," Henry started to say. "But take care of each other while I'm gone."
One last hug as they told him, "Be good" and "be safe" and then Emma and Regina left their son in his small, shared dorm room. Regina managed to hold it together from his room to the parking lot, but she was a mess as soon as they reached the Mercedes.
Emma pulled a fresh pack of tissues out of her pocket and ripped them open calmly but quickly. Wordlessly, she offered a few tissues to Regina and looked at her with empathy, her eyes watery and sad as she started to get emotional. The difference between them was that Emma kept it together. She had to, for both of them.
After Regina took the tissues and used them to wipe her eyes, Emma grabbed the keys out of the brunette's hand. "I'll drive," Emma said.
About half an hour into their trip back home, Regina had cried herself to sleep in the passenger's seat. Emma waited another ten minutes to see if Regina would wake herself up, but she didn't. The blonde then smiled to herself and drove home in silence, but she reached out a hand and took one of Regina's in her own. Regina remained asleep for the entire ride back and Emma held her hand for the same amount of time.
When Henry visited for Thanksgiving, he came home to find out Emma was a permanent fixture at the mansion and had been for almost as long as he'd been away. He also found out his brunette mother was capable of giggling and that his blonde mother was incapable of keeping her hands to herself.
