Title: 5 times a smart girl does something stupid for love… and 1 time she doesn't.

Dedication: Lila2 (look up her profile!) Because this fic was inspired by her similar Gossip Girl based prose-style pieces. This isn't a copy, it's my own work, but I owe her stories for the inspiration.

Summary: The women of Grey's Anatomy, and the stupid decisions they made in the name of love throughout the series, and then a decision that might have been the smartest one of them all. Various canon pairings will be explored. There'll be a few references to Private Practice where relevant. This is more character exploration than anything else.

Rating: If you're old enough to be appropriately watching the show, you're old enough to read this story. There'll be some non-explicit canon smut, some language, and reference to mature themes from the show itself. (K+/T)

Chapter 1: Addison

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Living in the trailer would have to have been the stupidest thing Addison Adrianne Forbes Montgomery-Shepherd had ever done for love. Well, maybe staying in Seattle in the first place after finding out that her husband was not only screwing some intern but was actually making doe eyes at her had actually been more stupid.

She was lying spread open on an exam table in the hospital's west wing, as far removed from the general chaos as possible, as a still-on-maternity-leave Miranda Bailey examined the poison oak littering her private parts. All this because she lived in a trailer, and had been walking Meredith Grey's dog. All because she loved Derek, and she wanted their marriage back, so she was willing to give his stupid trailer and his stupid new life in rainy Seattle a try, but it had been weeks since they'd put off signing the divorce papers and he still couldn't look her square in the eye.

Karma was definitely biting her in the vagina for– for what? For being in love with her husband, no matter what mistakes she made, and agreeing to live in a goddamn trailer on his newly-purchased land? Or was this about Mark, the fact that she thought she loved Mark and so she slept with him in a moment of weakness and vulnerability? Had it just been the fact that Derek had been an absentee spouse for a long time, and Mark was just there, but a classy Montgomery didn't do meaningless cheating sex (she wasn't her brother, for God's sake) and so she had needed it to mean something. So she moved in with Mark, and tried a relationship out for size. It quickly turned out that Mark loved his nurses and his sex more than he loved her, and she found herself having an abortion alone, because that wasn't how she had planned to have children, and Addison Montgomery was nothing if not a planner. Years later, she would remember something her mother Bizzy had always said: "People plan, and God laughs," and she would look back on her life and laugh at all the ironies too.

Right now, lying in the stirrups, all she could feel too honestly was that maybe, maybe the love had never been real or been enough anyway –with Mark or with Derek, because everyone knew Addison Forbes Montgomery wasn't a trailer sort of girl.

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Reviews are nice. Thanks for reading!

One more note: I have most of the characters and pairings I would like to explore already planned out, but if anyone makes a suggestion for a character I should write in the reviews, I'll take it into consideration and possible expand 5 times… into 6 times or 7 times.