Henry walked into Regina's office hesitantly. If he really wanted to go on a date, he would have to ask it in the gentlest way possible. He had no doubt that Emma would let him go with no problem. It was Regina that he had to worry about.

"Hi mom," Henry said. He relaxed as Regina smiled at him. She loved it when he visited her at work.

"Hey there," Regina said. "To what do I owe the pleasure of your company?"

Henry shifted awkwardly from foot to foot and chewed his lip. Regina narrowed her eyes. Emma did the same thing when she had something that she wanted to ask, but didn't want Regina to get mad.

"What's on your mind?" Regina asked. Henry looked up at her. How had she known?

"I want to go on a date!" Henry blurted. Regina's eyes widened in shock and her jaw dropped. Her little prince? Going on a date?

"Um. I, uh. Let me think about it," Regina said. Her mind was going into overdrive, and she could barely think, let alone speak. Henry nodded and quickly left the room before texting Emma.

Emma found the whole situation hilarious. It was the classical "he's my baby, so he's too young to be dating" scenario. It also probably didn't help that the only thing that Henry had texted was I think I broke mom.

Emma walked into Regina's office and couldn't help but slightly smile at Regina. Clearly the situation was getting to her. She had her head in her hands and was mumbling something about "little prince".

Emma walked over and put her hands on Regina's desk. "It's just a date Regina," she said. "We've had plenty of those."

"But we're grown women! He's just a little boy," Regina whined.

Emma chuckled. "Hate to break it to you love, but he's sixteen. Don't really think that qualifies as a little boy." Regina groaned and ran her fingers through her hair. Emma walked around the desk and kneeled in front of Regina's chair.

"What's the big deal anyway?" she asked. "It's not like he's going to get hurt."

Regina shook her head. "That's not it," she said. Several beats passed before Emma squeezed her knee, as if encouraging her to continue. Regina sighed. "I don't want him to be taken from me again."

Emma winced. She had been responsible for the first time that Regina had lost him. "Sorry," she said.

Regina just smiled. "I forgave you a long time ago dear. Plus you brought him back to me. I'm not sure he'll want to come back once he experiences love," she said.

Emma nodded. It made sense. "What if we watched them on their date?" she asked, smirking.

"Like a stake-out?" Regina asked, eyebrows raised. "Isn't that a little much?"

Emma shook her head. "We can just keep an eye on them and see how it goes. He'll never know," she said.

Regina leaned down and gave Emma a kiss. "Two things," she said. "First, you're a genius and I love you. Second, you have been spending WAY too much time with me."

Emma just laughed.

"So far so good," Emma whispered to Regina. They sat in her bug, far away from where Henry and his date were. They both had a pair of binoculars, and were keeping a close eye on Henry to see all that was happening.

Henry had done a good job planning the date. He had chosen to do simple things, but they were still fun. Both of the kids seemed to have a great time, and soon Henry was walking her home. Emma followed stealthily in her bug and stopped as Henry walked his date up to her front door.

Regina watched as both of them leaned in and shared a very hesitant first kiss. "Oh hell no," Regina growled. She unbuckled her seat belt, but Emma locked the car doors and grabbed her wrist.

"Easy mama bear," Emma soothed. "It was just a kiss."

"I don't know if you remember dear, but a kiss is how we got where we are," Regina said.

Emma laughed. "Gina, just because they kissed doesn't mean that they'll get married. They're high schoolers. Let them enjoy some romance. I doubt they'll even get married."

Regina huffed and sat back in her seat. "We'll see," she said.

7 years later, Regina pouted as she saw her little prince standing at the altar. Emma leaned over and kissed the pout away.

"I told you so, you know," Regina said.

Emma looked at her, confused. "Told me what?" she asked.

"On the night of Henry's first date with her. They kissed and I went to stop them. You stopped me and told me that just because they kissed doesn't mean that they were going to end up married. Well now look at where we are," Regina said, crossing her arms.

Emma smiled sympathetically. "He'll always be your little prince Regina. But if it makes you feel any better, you were totally right."

Regina just smirked. Of course she was.