Summary: Soon after moving to Boston to live with Emma, Henry begins to have regrets about leaving Regina behind. Meanwhile, believing that she's already lost Henry's love forever, a heartbroken Regina attempts to take her own life. Upon returning to Storybrooke Henry and Emma do their best to care for a fragile and recovering Regina. However all may not be as well as it appears.

TW: Attempted Suicide, Violence in later chapters. Deteriorating health of a major character. The story gets much darker in the second half.

~ Prologue ~

Regina was standing in the front hallway of her home, watching heartbrokenly as Henry and Emma walked up and down the stairs, carrying a carful of Henry's things out to Emma's yellow bug. It hurt Regina to see how happy her son was, knowing he was about to leave her for good and move to Boston to be with Emma. Did he really hate her that much?

"This is the last box," Emma announced as she descended the stairs. "Henry are you sure this is everything?"

"Yep, it's all there." He smiled up at her.

Regina bit her lip and shifted her gaze towards the ground to avoid the sight. She did not like this new arrangement one bit and it broke her heart to have to give up Henry. He was the only family she had left, and she loved him more than she had ever imagined a person was capable of loving someone else. But she felt she had no choice; he did not love her. He was depressed living here in Storybrooke and she needed to let him go in order give him the happiness he deserved. Even if it meant destroying her own in the process.

She hadn't given up custody of him, she would never have gone as far as that, but she hoped some time away would be good for him. His unhappiness had been growing deeper and deeper over the past few years and she had finally come to accept that she must have been part of the problem. Maybe she hadn't been cut out to be a mother after all. She had believed she had been doing a good job with him, that her love and care was enough, but obviously Henry disagreed.

As Emma left the house with the final box, Henry walked over to Regina who cleared her throat and looked down at him, trying to give him a smile. "You don't have to do this you know," she said gently. "It's not too late to change your mind and stay here."

"No it's okay, I want to go."

She crouched down to meet him at eye level. "Are you completely sure? You want to leave Storybrooke, your school, your home..." she was about to say 'and me' but she stopped herself because she knew he wouldn't change his mind because of her. In fact she was the reason he had decided to leave in the first place.

"Yeah, I'm sure." Henry grinned, clearly excited to leave.

Regina's voice softened and she tried to hold back her tears. "Okay, let's go outside then." She lifted her hand to Henry's shoulders in order to guide him out of the house but then stopped herself. This was a habit she had picked up a long time ago, maybe he didn't like it when she did this? She dropped her hand and instead she just followed closely behind him as he made his way to the driveway.

Once he reached it he turned back to her."Well, umm... bye!"

She paused for a moment and then reached down to pull him into the most meaningful hug she had ever given him.

It took Regina a few seconds, but when she was finally able to speak she whispered: "Goodbye Henry. I love you." Her voice broke as she tried even harder than before to hold back her tears, but her eyes were filling up so fast.

She never wanted this moment to end, she just wanted to stand here and hold Henry for the rest of her life. Why did he have to leave? She didn't want him to go, she had thought he would stay with her always, to finally be the one person who would never let her down. But she couldn't have been more wrong.

She had been about to kiss the top of his head and whisper another 'I love you', but Henry was obviously eager to leave. Before she could do anything he beamed up at her and started to extract himself from her arms, bereaving her of the chance. Henry slid into the passenger seat and shut the door behind him. He fastened his seatbelt while Emma started the engine, and Regina felt her heart tug painfully in her chest at the sound.

She wanted to change her mind, to tell Henry she wouldn't allow him to go to Boston after all. She would have been within her legal right to do so, but it would have shattered any last hope she had of regaining his love. Instead, she swallowed her words and blinked back the tears, refusing to let them fall.

"Call me when you get there okay? Just so I know you've arrived safely." Regina said, placing her hand on top of Henry's where it rested on the sill of the rolled down window.

"Okay." Henry replied distractedly.

Regina's hand slipped against the doorframe as Henry removed his hand from the window. He looked to Emma, excited to start their mini road trip.

"Bye Regina!" Emma smiled around Henry from the driver's seat.

This caused anger and resentment to boil up inside the Mayor. How dare she. Emma had been the one to rip Henry away from her, the son she loved more than anything else in the world, and Emma was acting as cheery as could be.

Henry waved at Regina through the open window and the car began to pull away.

"I'll miss you." She said, though she was sure it had been too quiet for him to hear.

Trying her best to force a smile for Henry, Regina gave a small wave back as they drove away. As soon as the yellow car turned the corner the tears began to fall rapidly down her face. Folding her arms tightly around herself, she breathed a heavy sigh of despair and turned to go back into her house, alone once again.

A/N: Thank you for reading, please let me know what you think so far :)