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Gabriel put the finishing touches on the trick he had planned for Dean. Just a few more pies here and some very attractive women in bikinis there and everything would be perfect. He wondered what else Dean would like. If it were him, he'd be having candy bars everywhere, maybe some cake, and definitely more women. He specifically picked out some of the best models featured in "Busty Asian Babes" since he knew that was Dean's favorite magazine, so this had to be spotless! Dreams hadn't worked, so he needed to spice Dean's life up with a nice trick!
Gabriel also had to pick the right time to spring this on Dean, a time when he wasn't depressed, but also a time when he wasn't too happy; this might be the right way to cheer him up, but he doesn't want to take that away from Dean. Instead, he picked a time when Dean was feeling tired after his average day, but not completely exhausted. He wouldn't have any problems walking into a nice room of women and pies after an average day like that!
Gabriel also decided to stop dreamwalking. Not only was that making Dean feel worse, but he began fearing Dean's interpretation of the dreams. If he perceived them as nightmares, then Dean might not believe him when Gabriel showed up in person. It was a long stretch enough to prove himself to be alive after what Dean had seen, but now he also had to prove that nothing had changed - Gabriel still loved Dean. That was going to be the hard part, especially after Dean losing both him and Sam within such a small period of time.
Weeks passed by and the perfect time never came. Gabriel began seeing the emotional side of Dean while he watched from afar. Dean was never content, despite living with a great woman. She was kind (from what he saw), doting, and had a sweet kid that looked up to Dean. Gabriel began to scratch his idea of the trick when a new idea formed. He grinned happily as he thought of the perfect method to cheer Dean up.
It took one small snap of his fingers to alter the grocery list with a small addition; ingredients for a homemade cinnamon apple pie, with the recipe stapled onto the back made its way into the kind woman's hand. She went shopping later that day and immediately went to preparing the pie after getting home, a smile on her awaiting face. A small tear fell out of Gabriel's eye as he began to realize he'd not be able to give Dean the pie in person, but it'd be worth seeing a smile on his face again.
After one bite, Dean's face looked similar to the look he made after an orgasm, but it quickly changed. Confusion? He was also yelling, interrogating in fact. What about? The woman took out the list with the recipe stapled to it, and Dean's expression changed. He looked out the window, around the house. Gabriel swore that Dean knew he was there. Looks like he wasn't going to need that trick after all. He would try dreamwalking one more time.