Chapter 2

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Dean's POV
I never thought when I was sad on my couch in my dinky little apartment that I would be spending my Christmas vacation swimming with fricking dolphins, but here I am. Not gonna lie, they're graceful as fuck in the water and it's really something to watch them go about. Cas wasn't lying about this being an experience. It was nice to see Cas happy as he petted a dolphin who looked a bit smaller than all the others. Maybe it's a baby. Super cute. Cas and the dolphin make an adorable duo too.

I'm never really spent time with Jimmy since we just haven't crossed paths much. Cas went to the same college as me, even though I dropped out, but Jimmy went to a different college in a totally different state. I've talked to him a few times on the computer when I walked in on Cas video chatting with him, but this is the first time I've seen him in the flesh. They really do look alike, but their personalities are quite different. Jimmy was a bit more do something and think later while Cas is the opposite. I've met Amelia a few times, but it's always been mostly small talk with her. She seems nice like I remember and I can tell she and Jimmy really do love each other.

When we got back from our boat ride, we all decided to chill at a table near the pool. I offered to grab us some drinks and Cas came with me to carry them, but once I got near the bar I froze like lamp pole in winter.

"Dean? Are you ok? Dean." Cas said, waving a hand in front of my eyes.

"Can you get us the drinks? I'll help carry them to the table, but...." I said, eying the bartender a few times until Cas looked over.

"Is....is that Cassie?" He asked and I nodded.

"You understand.....right?" I asked, giving him my best smile to persuade him to do the talking. He just sighed a bit hard and rolled his eyes before walking up to the bar. Of course he motioned for me to come over once he was finished talking, so of course Cassie saw me anyway.

"Dean Winchester. What a sight."

"We just want our drinks.....please." I said, my stomach wanting to jump off a cliff. She just huffed and made our drinks without another word. The walk back to our table was just as quiet, Jimmy breaking the silence as he looked a bit too excited for alcohol. Down boy, it's only a bit after 3 pm. It's not happy hour yet, buddy. We drank in a somewhat comfortable conversation. When we parted ways, I went back to my room to see Sam getting dressed.

"Deciding on a tie? Where you going, fancy pants?" I asked, smirking at him as he rolled his eyes in the mirror at me.

"Gabe is taking me out to dinner. All he said was dress nice, so I'm not sure what to expect besides it probably being cliche romantic. Is a tie too much? Would it be better to roll my sleeve ups?" He said, looking oddly nervous for once. Coming over to him, comparing the 2 ties he had against his shirt, ultimately tossing them on his bed and unbuttoning the first button and adjusting the collar.

"There....I think that's good. Rolled sleeves is up to you, but you look fine as is. You ok? You look like a high schooler going on his first date." I said, Sam fixing his hair in the mirror as he swallowed hard.

"In a sense.....it is our first proper date."

"Really? You live in California, dude. That's like the gayest state besides Connecticut."

"I know....but....I'm not out at the firm and I live near a few of my coworkers, so I've been dating Gabe in sort of secret. Being able to be open here, Gabe wants to treat me for once, but I'm all over the place." He said, still fixing his hair, making me slap his hand out of the way to do it for him. Big brother mode was breaking out. Once he looked nice, I patted his shoulder and gave him a pep talk.

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