Olicity Travels, Day 2: Meeting the Winchesters

For my second installment of #OlicityTravels Oliver and Felicity run across a familiar trio from the world of “Supernatural.” :) This is a bit long and borders on fan fic. Contains mild spoilers for all 11 seasons of “Supernatural.”

(AN: I’m not able to do a whole lot of traveling this year, so I decided to do #OlicityTravels from my apartment using Funko Pops (because I have way too many of them). I’ll be on vacation at the end of the month, so hopefully they’ll be able to get out of the house then! )

Oliver and Felicity stumble across some strange happenings when they stop at a diner in a small town in Kansas. They agree to investigate, and in the process they run into two “hunters” and “an angel of the lord” who are already on the case.

“Oh my god!” Felicity shrieks. “You guys are REAL?!”

Oliver looks at Felicity in confusion, and after babbling on for half a minute about something involving a series of books, Felicity shakes her head and promises she’ll explain it to him later. After she introduces herself and Oliver to the three strangers, the tallest of the men introduces his own group. The hunters in plaid turn out to be two brothers, Sam and Dean Winchester, and the angel’s name is Castiel, or “Cas” to his friends. Dean insists that the five of them are NOT friends, however, and proceeds to tell Oliver that they don’t need any help - they’ve got this covered, thank you very much. Oliver admits that, funnily enough, he was about to tell Dean the same thing. Dean and Oliver look ready to go toe-to-toe when Sam and Felicity step in and pull them apart.

Sam urges his brother to let them help, and Cas advises the same, assuring Dean that Oliver and Felicity will be able to offer the type of help they’ll need for this case (namely Felicity’s computer skills and Oliver’s prowess with a bow and arrow). Meanwhile, Felicity reminds Oliver that he’s supposed to be learning to let people help him.

In the end, Oliver agrees (because if it’s Felicity asking, he’ll do it) and so does Dean (because he can’t say “no” to Sammy).

Oliver and Felicity squeeze into the back of the Impala with Cas, and Dean drives them off to the Men of Letters bunker, grumbling all the way about how “two hunters, an angel, a vigilante, and a hacker” sounds like the beginning of a bar joke. In an attempt to break the painfully awkward silence, Felicity and Sam begin to chat, and it becomes clear to Dean that not only is Felicity gorgeous but she’s also funny and smart. It’s not long before Dean starts to hit on her, oblivious to the daggers Oliver glares at him from the backseat. When Dean offers to take Felicity out for drinks when the case is over, Oliver growls “she’s my girlfriend” in a shockingly good impersonation of his Arrow voice. Felicity shakes her head at Oliver and smiles before kissing him soothingly on the cheek, and when Dean grumbles in disappointment Sam has to bite his tongue to keep from laughing.

Though the point’s already been made, Oliver doesn’t waste a chance to kiss Felicity firmly when they reach the bunker.

Once they’re inside, “Team Super Arrow” (“please don’t call us that, Felicity”) gets to work researching the Monster of the Week. After three hours of fruitless research, they take a break for some food. Sam and Felicity quickly bond over all things Geek, and Oliver finds himself gravitating toward Castiel (Oliver has a few questions for the angel, but in the end he doesn’t need to ask them; Cas assures Oliver that Tommy and his parents are all incredibly proud of the man he’s become).

Dean feels a bit left out at first, but in the end he shrugs and leaves to get another beer.

Eventually, Team Super Arrow (“FELICITY!”) decide they need a bit more help, and Sam suggests they call their friend/father figure Bobby Singer (~~who totally isn’t dead, I don’t know what you’re talking about).~~

Turns out, Bobby doesn’t need to do any research; he already has the answer they’re looking for. After a brief explanation of the monster they’re facing and what they need to do to kill it, Bobby calls Sam and Dean “idjits” for waiting so long to call him, then hangs up the phone so he can continue to enjoy his retirement in peace. Dean remarks that Bobby seems to be getting grumpier in his old age, and Sam just hopes that he and Jody Mills are enjoying some quiet time alone together. Dean shudders at the thought of “old people sex” and Oliver wonders how the hell these two get anything done.

That night, the team heads out to face the monster, leaving Felicity behind in the Men of Letters bunker to be their eyes and ears in the field. But in the end the team miscalculates, and instead of showing up at the power plant like they were expecting, the monster finds its way into the bunker – with Felicity. A combination of Sam’s quick thinking and Castiel’s ability to teleport gets them back to the bunker just in time. In an incredible show of bravery, Dean saves Felicity from the monster, allowing Oliver the opportunity to strike it through the heart with a silver tipped arrow dipped in blood.

With the monster defeated and the fight over, Oliver offers to stitch up the gash on Dean’s shoulder, and when he’s done he shakes his hand and thanks him for saving Felicity’s life. Dean shrugs and insists it was nothing, but a mutual respect grows between the two men. Before things can get too chick-flicky, Dean insists that they go out and celebrate.

Team Super Arrow (*sigh* ”Fine, Felicity”) have a few drinks at a local bar, and Oliver proceeds to wipe the floor with Dean during a game of darts. Dean’s man enough to admit when he’s beaten and accepts another beer from his brother. Meanwhile, Felicity kisses her “big, strong, handsome” boyfriend hard on the mouth and drags him out of the bar, suggesting: “we should head back to our hotel room so you can show me just how good your aim REALLY is” (Dean fist pumps the air in response, while Sam looks mortified and Cas complains: “I don’t understand that reference”).