The Arrangement Masterlist
Summary: in an AU where the Winchester family owns a multi-million dollar company, Dean’s in a bit of a pinch. Grandpa Samuel is threatening to cut him off if he doesn’t straighten out and stop getting into trouble. Instead of taking some responsibility, Dean comes up with an ingenious plan: find someone to pretend to be his girlfriend. You and Dean have never gotten along, but a fake relationship seems to be beneficial to you both…
Part 2 - Sam disapproves of your little arrangement, and you and Dean have you ‘first date’
Part 3 - Dean reflects on your first date, and makes plans. The second date goes a little better, and Dean finds out how good your acting skills really are.
Part 4 - You spend the night at Dean’s place
Part 5 - Dean struggles to deal with the rest of the morning, and then gets an unexpected call. The two of you go on a double date with Sam and Jess.
Part 6 - Jess informs you about Dean’s past, and Sam teases Dean. After dinner, Dean brings you home to find someone unexpected waiting for you, and helps you deal with it.
Part 7 - Dean meets your mother, and you go dress shopping with Jess.
Part 8 - You and Dean head out to his hometown, where you finally get to meet Mary and John. The sleeping situation causes some minor problems.
Part 9 - You and Dean have an interesting morning, but Sam interrupts. Later, you and Mary have a little heart to heart, and Dean says something surprising.
Part 10 - The gala finally arrives, and Dean is absolutely floored by your dress. An interaction with Samuel leaves Dean fuming, but you calm him down. Dean finally admits his feelings.
Part 11 - Dean reflects on the evening, and the two of you have a talk
Part 12 - someone delivers some unexpected and unpleasant news, sending you running. Sam and Benny confront Dean, and the three of them go looking for you.
Part 13 - you head to the only safe place you can think of. A talk with your father gives you the courage to return to work, where Dean finds you immediately. But he’s not expecting your reaction. Charlie and Cas come to the rescue.
Part 14 - Dean tries to cope with your breakup, and then gets a surprise visit from Crowley. Your friends take you out to try and cheer you up, but eventually you head home alone, only to find someone waiting for you.
Part 15 - You have an encounter with Mark, and Dean shows up just in time. The next morning, the two of you talk things out. Sam arrives with some news.
Part 16 (conclusion) - Dean responds to Sam’s news. The two of you pay a visit to Samuel, who lashes out. Secrets are revealed and threats are made, leaving you reeling. You and Dean discuss the future.
Epilogue - A few months after the events of part 16. Sam and Jess’s wedding, a housewarming party, and revealing conversations.
Epiloge Part 2 - The Fourth of July finds you and the Winchester clan at the lake to celebrate the holiday. Jess shares some news and Dean surprises you with an important question.