When Regina had cast the curse 18 years ago, it was with the intentions of taking away everyone else's happy endings, and fulfilling her own. She was Mayor of Storybrooke, ruling over her subjects just as she did as the Evil Queen back in the Enchanted Forest. And yet, she wasn't happy. The hole in her heart still caused it to ache endlessly, and she yearned to fill it.
You were one of the townsfolk in Storybrooke under the influence of the curse. You knew to steer clear of the Mayor; her reputation for stoicism and harshness proceeded her. The woman's power and dangerous allure were known to all, and nobody wanted to cross her. But amidst all of that, you couldn't help but notice that Regina seemed incredibly lonely. She spoke to Sydney on business terms, but that was about it.
But that all changed one day. When Regina went out of town to Boston, and returned in the afternoon with a little baby boy. Gold had found Henry in an orphanage in Boston, and Regina had adopted him. So now the Mayor walked around Storybrooke with a little bundle wrapped up in his seat. You'd never seen her as happy as she was with Henry. Until he started getting a little.. vocal.
Regina couldn't figure out what she was doing wrong. She had fed him, burped him, changed him, coddled him; but Henry just kept crying. Between her work and caring for him, the Mayor was beyond stressed, and she was beginning to feel desperate to find out why Henry didn't want her.
You ran into her, in fact, at the park. Regina had thought that maybe the change of scenery would soothe Henry. Subsequently, it hadn't worked, and she was now sat on a bench with him in her arms, rocking him gently.
"Come on.. please stop crying, Henry.."
She pleaded with her infant son, exhaustion seeping from her being. Regina looked just about as distressed as the wailing baby in her arms, and the sight was enough for you to stop and considering going over to her.