A/N: Song fic based off "A Beautiful Mess by Jason Mraz.

She was a complicated woman that much he knew. He'd known it back in their land as she stood before everyone at her almost-execution, and declared that she felt absolutely no guilt for the pain she had caused. It wasn't until they were brought to Storybrooke that he'd seen just how deep her issues ran. And her recent sessions with him had been even more revealing; considering everything she had been through, it was no wonder she had turned to magic.

Although you were biased I love your advice, your comebacks ‒ they're quick
And probably have to do with your insecurities

Their sessions together at first had been… interesting to say the least. Everyone conversation with her had been a battle of wills that she insisted in engaging in with him. Funny enough, it wasn't until he stopped trying to get her to open up that she began revealing bits and pieces of herself to him.

Most of their discussions focused on her relationship with Henry, since he was her motivation to try and change. She kept things close to her vest, but Archie had always been good at reading people and it was obvious that her relationship with her son mirrored her own relationship with her mother. Cora. The name had come up once or twice, and then been quickly dismissed by wave of her hand and a change of topic by Regina.

There's no shame in being crazy, Depending on how you take these
Words I'm paraphrasing this relationship we're staging

It had taken some time, but finally it seemed like she was letting him in and actually listening to his advice. She was even starting to take an interest in his past, which made him a little uncomfortable but at the same time showed how much she was changing. There was no way he'd ever tell her about his own past; these sessions were to help her, not for him to reveal personal things about himself.

He couldn't help but see some of the similarities in their upbringings. Both of them had been raised by emotionally abusive parents, both desperately wanted to be good and both had ended up turning to Rumplestiltskin for help. It made him wonder what would have happened if Regina had been the one to wish on the Blue Star instead of him; maybe it would have been her conducting the sessions and him on the couch.

And what a beautiful mess, yes it is
It's like we're picking up trash in dresses

By now he'd gotten used to her snarky comments; it seemed that every time they went deeper into her issues, she felt like she had to balance it out somehow. They'd now been toned down to remarks meant to tease, not to hurt really. Although, he could do without all the bug jokes. No matter how many jokes she made, or how much she tried to divert his attention, it was obvious that a lot of her behavior stemmed from insecurities created in her childhood.

Eventually they'd taken some of their sessions outside, it seemed to help Regina relax and open up even more. And she and Pongo seemed to have develop some kind of connection, and so he would often take Pongo with them when the weather was nice enough. His dog seemed to like and trust her quite a bit which further confirmed that he wasn't wasting his time in his sessions with the former Evil Queen. Dogs could often sense things that people couldn't, and if his dog was comfortable around Regina then that could only be a good thing.

Well it kind of hurts when the kind of words you say
Kind of turn themselves into blades

He was startled from his musings when a soft knock came at his office door. Smiling to himself, he made his way over and opened it to reveal the woman he had just been thinking of standing there.

"Hello Regina. Ready to get started?"

She tilted her head slightly and gave him a funny look. "How can you always be so cheerful," she remarked as she walked over to the couch and made herself comfortable.

"Would you rather I frown at you from now on," he joked as he got his notebook and settled into his chair.

There was a pause and then- "I didn't say it was a bad thing Dr. Hopper."

And "kind and courteous" is a life I've heard
But it's nice to say that we played in the dirt
'Cause here, here we are, here we are