Chapter Text
Dean Winchester was not lonely. He wasn’t annoying or ugly. Dean was a pretty cool guy. Too bad no cute guys in a 100-mile radius had realized that, yet. In all honesty, Dean was pretty great. He had a nice job, a nice car, and he wasn’t bad on the eyes. So, why was he sitting on his couch five days before Thanksgiving, scrolling through the “casual encounters” page on Craigslist? Shut up.
“This is my life now, Honeybee.” Dean turned to his kitten (yeah, macho man, Dean Winchester, has a kitten named Honeybee. Crazier things have happened), who was curled up beside him, and hung his head in shame before resuming his pathetic scroll of shame. “All this and I still show up home with empty arms on Thanksgiving. I can hear Sam’s bad jokes already.”
After what felt like forever of scrolling through admittedly uncomfortable descriptions of the “encounters” some people were looking for, Dean found one listing that piqued his interest. The listing was titled, “Alone on Thanksgiving? Mad at your dad? I can help.” Figuring it couldn’t hurt just to see what the original poster had to say, Dean clicked on the link and he was in a fit of laughter from the beginning. How could this guy be serious?
I am a 28 year old felon with no high school degree, and a dirty old van one year younger than me painted like Eddie Van Halen’s guitar. I can play anywhere between the ages of 20 and 29 depending on if I shave. I’m a line cook and work late nights at a bar. If you’d like to have me as your strictly platonic date for Thanksgiving, but have me pretend to be in a very long or serious relationship with you, to torment your family, I’m game.
I can do these things, at your request:
openly hit on other guests while you act like you don’t notice.
start instigative discussion about politics and/or religion.
propose to you in front of everyone.
pretend to be really drunk as the evening goes on (sorry, I don’t drink, but I used to. A lot. Too much in fact. I know the drill).
start an actual physical fight with a family member. either inside or on the front lawn for all the neighbors to see.
I require no pay but the free meal I will receive as a guest!
Dean was in tears of laughter by the time he finished reading. He could just picture this guy trying to talk politics to his dad or hitting on one of his family members in front of his mother. And this guy was willing to do all of that for a free meal? Holy Jesus on a toothpick, this guy was nuts. After he finished laughing, Dean turned his phone off, picked up Honeybee, and saw himself off to bed. And if all he dreamt of were hilarious Thanksgiving dinner scenarios, no one had to know.
When Dean got up the next morning and turned on his phone, his body and mind felt heavier. His phone had a few notifications, all of them text messages from his mom, saying how excited she was for him to come home for Thanksgiving. The dreaded family holiday was officially four days away and Dean had no one to show off to his family. At least Sam had Jess and Adam had Michael. Dean was 26 and was still perpetually alone.
As he went through his morning routine, he humored the idea of actually bringing Craigslist Guy (he didn’t put his name in the listing so that’s what Dean named him) with him. If anything, Dean could just take him as a friend, which was much more than he had at the moment. Halfway through his bowl of cereal, Dean looked at Honeybee, who was curled up in front of the fireplace, and let outa sound that was somewhere between a sigh and a groan.
“Fuck it.” Dean grabbed his phone off of the table and pulled back up the listing from the night before. After wrestling with his mind over how in the hell he was supposed to word his message, he finally typed something up and sent it out before throwing his phone at the couch to finish getting ready.
Sent: Hello. I’m messaging you about the Thanksgiving thing. Just wondering if someone’s already filled the spot or if you’re still free.
Once Dean was finished getting ready and heading out the door, he picked his phone up to find that the guy had responded to his message.
Received: Hello. No, I’m still free, if you’re interested.
Sent: Sounds good. Just to avoid calling you Craigslist Guy, what’s your name?
Dean’s phone dinged again as he was getting in his car.
Received: Castiel. What’s your name? So I can stop calling you Thanksgiving Guy.
Sent: Dean. Hey, is it cool if I give you my number so we can talk about meeting up to go over details?
Dean’s phone went off as he was driving but he waited until he got to work to check it.
Received: That seems agreeable.
Sent: Okay. It’s 678-999-8212. Talk to you later, Cas :)
As he walked into the garage, he mentally scolded himself for using a smiley-face in a text message. For Christ’s sake, he was almost 30. His thoughts were cut short when a strong hand clapped him on the back.
“Hey, brotha. You look mighty happy today.” That was Dean’s ‘kind of-friend’ Benny. They worked together and they hooked up once while they were both black-out drunk. It wasn’t that Dean didn’t want to be friends with the guy, it was that didn’t know how to be friends with people. He had a hard time finding people that shared his interests.
“Morning, Benny. Just well rested, is all.” Dean hid his discomfort and changed into his coveralls before sliding underneath a jacked-up car and beginning his work day. By the time his lunch break rolled around, Dean sat in the break room and pulled out his phone to see that he had a text message from an unknown number.
Unknown: Hello, Dean. I had no clue when ‘later’ was so I didn’t know how long I was supposed to wait. But, now you have my number so you can text me when you feel like it.
Dean: Hey, Cas. Yeah, sorry, ‘later’ is kind of a vague window I guess.
Cas: Yeah it kinda is lol. Hey, would you mind to send me a picture of you so I know I’m not talking to a 50 year-old crazy man?
Dean wrestled with himself once again and decided to just send a picture. He snuck out of the break room and into the bathroom, locking the door behind him. After finding a good angle that wasn’t too sweaty or oil smudge-y, he took a picture of himself and sent it, not giving himself a chance to chicken out.
Dean: [image attached]
Dean’s lunch break ended 15 minutes later and Cas still hadn’t responded. Dean took that as a sign that Cas was not interested in being his platonic or not-platonic date. Oh well, there’s always Plan B (also known as, show up alone and get super drunk). A few minutes after he had gone back to work, Dean’s phone chirped, letting him know he got a text.
Cas: Dean, I just spent 20 minutes trying to reverse image search that photo because there is no way you actually look like that.
Dean’s cheeks heated up and flushed a bright red, much to his chagrin. Dean knew he wasn’t ugly but something about someone else complimenting him added a different feeling to it.
Dean: Now it’s your turn, dude.
Cas: [image attached]
Dean: We should definitely meet up to discuss this.
Cas: Ha okay. Roadhouse @ 8 tonight?
Dean: It’s a date.