Chapter 5:
What was Dean planning? Booze? Women? Pool hustling? All of the above? Sam sat in the Impala with a puzzled look on his face as he thought about this. Dean took that as his cue. "Dinner, Sammy. Nice restaurant, smooth jazz or somethin'. Could be really nice." "She sounds like a lucky lady." Sam replied as he stretched his arm out, one of them gently running across Dean's shoulder. "I uh.. was actually wanting you to go with me." Sam noticed Dean's face and the tips of his ear were beginning to turn pink and that his cocky attitude was starting to disappear. "You're joking right?" Sam asked. "If you want it to be a joke, it will be." Dean forced himself to chuckle slightly. "No! That.. That sounds great." The steering wheel then became a drum set for Dean's wildly moving fingers. He didn't want to say anything else, because he feared he would do something wrong and Sam would change his mind.
…
When the Winchesters arrived at their next motel, their was a new sense of awkwardness between them. Dean found himself staring at the simplest things about his brother that he hadn't noticed before. Like the way his shirt scrunched up a bit when he was getting their duffle bags out of the trunk, exposing just enough back muscle to make his heart beat just a little faster. Desperately he tried to push the feeling deep down inside him. Sam had been doing the same thing, noticing every little thing Dean did that was considered even remotely attractive. His bowlegs as he walked and every freckle seemed to be situated at exactly the right spot. The tension was killing Sam, but he didn't have to courage to do anything about it.
"I'm gonna take a shower." Sam stated as he yawned then pulled his shirt off and headed toward the bathroom. Dean tilted his head slightly and watched Sam walk away. Damn back muscles. He thought. The older Winchester needed a shower as well, but he wasn't just going to run in there and say, "Hey! Sammy, wanna shower together like when we were little?" He had to find another way to occupy his time. So, he pulled out one of his sawed off shotguns and started cleaning it. There wasn't much else to do anyway.
A few short moments pass and Sam emerged from the bathroom, clad in only a towel hanging lowly around his waist. Dean turned toward his younger brother and gasped softly. Luckily, Sam thought nothing of it. "I'm gonna hop in now." Dean said and was in the shower within what seemed like seconds. It then took the shower water at least a solid four minutes to get up to its full heat though. He allowed the water to run completely through his hair, then he rested his head against the wall. After a few moments, he began rhythmically banging his head against the tile, in an attempt to get all thoughts of Sam out of his head. It didn't work.
Dean appeared from the bathroom in a shirt and his boxers and while he was gone, Sam had done the same. Hundreds of times in his lifetime Dean Winchester had seen his brother like this, naked too, but now everything seemed different. Was it because Sam was close to death? He didn't know. Whatever it was, it was going to eat at him no matter how hard he tried to push it down.
Sleep evaded Dean for most of the night. His mind was too occupied with all these stress filled thoughts. What am I going to wear? and Does he think this is a date? Dean never really cared about what he was going to wear. Why was now any different? And if Sam thought this was a date, if needed, Dean could easily play it off and say he just "wasn't in the mood" this Valentine's Day. Hours Dean spent thinking every last detail of this "dinner" through. He wasn't going to mess up and create something even more awkward than it already is.
When morning came, Dean was staring at the ceiling and beginning to regret purposing that they go to dinner together in the first place. Sam yawned, then rolled in the end so he was facing his older brother. "You still wanna," Another yawn. "Spend Valentine's Day with me and not some busty blonde?" "You kidding? I'd pick you over busty blondes any day." Dean said it in a tone that sounded partially sarcastic, so Sam just said, "Okay." Then rolled back over and went back to sleep.
Dean decided to get up. He took a quick glance around the room to see if there was a coffee machine. There was. Now he wouldn't have to deal with his brother's wrath. Plus, he needed something to get him up and going, but the older Winchester feared that it wasn't going to be strong enough.