A/N: Well, I'll admit it. I kind of like Lisa. Especially if the other option for Dean's love interest is Cassie (sorry but there was something about Cassie that made me want to slap her).
It's hard loving a man like Dean.
Lisa knew that from the get go, back before the changelings, before Ben even. When they'd both been young and it had been fun and that's all either were after. She'd known that falling in love with Dean wouldn't be smart. He was just a once in a life time kind of thing. He'd been so in love with life back then, so alive. There was no way to hold on to someone like him. Falling in love would be a mistake. She thought she'd dodged that bullet when she watched him leave, and she only had a smile to show for it.
The second time he rolled back in her life, not quiet a decade later, and not quiet so in love with living life she'd guarded herself, for Ben's sake. No matter how strong the temptation was, or how good those old memories were. There was no room for wild men that were good for nothing but a good time; except, Dean proved her wrong. Swooping in to save the day even when she tried to shut him out, only to ask for nothing in return. Showing her she had him figured out all wrong, still, she'd known it wouldn't be a good idea to fall for him. He wouldn't, couldn't, stay. Something told Lisa Dean was resigned to his fate, whatever that maybe, and would not change his mind for anything. Even so, when she watched him drive away, for the second time, leaving her with a smile and her son whole and safe, she let him take a little piece of her heart.
When he was on her doorstep for the third time years later, Lisa realized that he'd gotten a bigger piece of her heart than she'd thought. He was looking desperate, and promising things that worried her. With the way he was talking and how determined and final he seemed, she knew this was the end, of what she couldn't began to guess at, but it scared her. Dean wasn't going to be okay and she only wanted to help him because he'd saved Ben, and he was a good man, and there was something close to fear in those green eyes. She knew it had to be something terrible for him to be so desperate. So when she watched him drive away, the smile was forced, because she was scared for him but she still believed in him and his strength.
Later, when it was over and Dean, strong, solid Dean showed up broken and shattered she let him in. She held him as his tears came and offered shelter from the world that had all but destroyed him. As the minutes turned into days and days turned into months she stayed steady and strong for him.
There were times when it wasn't easy. Dean had nightmares that seemed to refuse to let him wake, and the best she could do was sit with him till they passed. There were the questions from her mother and friends about who he was, and why would she let him just suddenly move in when she'd never had a steady relationship before? Then she had her own worries about how this was affecting Ben, but those were forgotten as she soon realized that Ben seemed to understand Dean better than even her. The two of them seemed to be cut from the same fabric.
She wasn't jealous or upset when she saw that Ben was more of a comfort to Dean than her, she was only relieved that Dean had found something that helped. Lisa wasn't so arrogant to think she could fix Dean. She didn't try to put him back together, because only one person could ever do that and that person was gone. She only tried to help him hold on, still believing in his strength.
When Sam came back, and they put each other back together, and it came time for Dean to leave again. He came to her, with life back in his eyes and an apology that he had to go. Lisa assured him he had nothing to be sorry for. She told him to pay them a visit every once in awhile, if not for her then at least for Ben.
Dean smiled like the first time she met him, and she realized that there really had been no one else for her. If that was a good or bad thing she wasn't sure, but she knew there was no changing it. It was her own fault for falling in love with him, because she'd always known she couldn't keep him. There would probably never be anyone else, because he would be the standard she'd compare by and every other man would fall short. She almost told him she loved them, asked him not to go. It was a weak and selfish moment on her part, but it passed. Instead she kissed him, smiled and told him she was happy for him. The couple of tears that managed to slip out were wiped away with a tender touch and a promise she won't hold him to. She couldn't be upset about losing him, not when he was never really hers in the first place.
Lisa and Ben, side by side, watched him drive away, and with a genuine smile because this was right. This was how Dean was meant to be, what he was meant to do, and it was good to see him that way again.
Loving men like Dean isn't supposed to be easy, and that's just the way it is.