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The rest of the day for Emma went completely interruption free, she was left alone in her office to get a head start on all the paperwork Regina had led on her while at their lunch together. Emma was pleasantly surprised that her lunch with Regina went off without a hitch, they laughed and chatted about absolutely nothing while they waited for their food to arrive and then after that they talked work and budget reports for the rest of the afternoon, until Regina had to head back to the office to get up to date with her own paperwork.

This left Emma to her thoughts about whether or not she was doing the right thing by going on this date with Hook, she feared that this might upset Henry even more since it hasn't been long since he lost his dad. So she made the decision that she would talk to him first before actually going on the date tomorrow night.

"Hey, kid!" Emma shouted before running over to meet Henry at the school gate. The tall boy was currently standing beside Mary Margaret and David who had offered to pick Henry up.

"Mom? I thought David was picking me up." Henry said confusingly.

"Yeah well I finished early so I thought you and I could go down to the beach for a while, maybe get an ice cream?" Emma suggested while bumping shoulders with her son.

"Sounds good to me! See you later!" He said to Mary Margaret and David before walking away with Emma towards the beach. Leaving Mary Margaret and David smiling at their daughter and grandson walking away.

"Did you actually get your work done or are you just avoiding my mom?" Henry asked while walking beside Emma with a large chocolate chip ice cream in hand.

"Believe it or not, I actually finished everything!" She laughed before taking a big lick of her strawberry ice cream.

"Okay, I'll believe you this time...It's been a while since we've done this." Henry looked over to Emma who simply smiled at him.

"Yeah, I figured that after everything that's been going on lately we could use a catch-up. We haven't really had a chance to catch up since we got back." Emma stopped and gestured for him to take a seat on the bench that faces the sea. Silently Henry takes a beside his mother on the bench. "We haven't had a chance to talk about your dad..." Emma said quietly, but not too quiet so Henry could still hear her.

"I miss him, mom..." Henry replied quietly without looking at Emma.

"I miss him too Henry…" Emma said, leaving it at that. She knew that this was not the right time for either of them to be talking about this, let alone for Emma to be talking about Hook to Henry.

"I don't think he'd want us to be like this…" Henry said surprising Emma.

"What do you mean Henry?" Emma asked concern creeping onto her face.

"He wouldn't want us sitting here and moping…he'd want us to move on and enjoy our lives," Henry explained while placing his hand on top of Emma's.

"You know for someone who hates school so much you sure are a smart ass!" Emma joked before pulling him in for a long overdue hug.

"Mom…I know what you wanted to talk to me about." Henry said while looking up at Emma.

"What?" Emma questioned the boy.

"I saw you talking to my mom earlier…you don't want me to stay with you anymore do you?" Henry questioned sadly.

"What?! Henry that is not what is going on! Your mom and I were just going over budget reports! Of course, I want you, you're my son Henry and nothing is going to change that okay!" Emma exclaimed before pulling Henry in close for a bone crushing hug.

"What did you want to talk to me about then?" Henry asked while wiping a tear away from his cheek.

"I kind of agreed to go on a date with Hook…but only if you are okay with it. I won't go if you don't want me to Henry." Emma quickly explained.

"I think it's a good idea I guess…it's what dad would have wanted," Henry smiled proudly at his mother, before resuming to eat his almost melted ice cream.

"It's only one date, it's not like we are getting married Henry!" Emma joked before returning back to her ice cream as well.

Regina sat in her home office nursing a glass of strong apple cider and going over the budget reports from the sheriff's department that Emma had surprisingly sent over on time for once. Even though she was going over paperwork, her mind was far from work. All she was able to think about was how she was going to win Emma over. Not because of this stupid bet with Hook, but because she knew that right from the first time she met her on her doorstep a few months ago that she was the one that she was meant to be with and there was no way in hell was she going to let some pirate who only wants a quick lay get to her first.

She had to think of something smart and fast, something that wouldn't give away her feelings just yet. 'I could always take her up on her family night offer' Regina thought to herself before smiling wickedly. She knew exactly how she was going to do this, but first she may need some help.