When first introduced, Reilly is a cocky, selfish, irresponsible, stereotypical junior hockey player. As the series progresses, however, he shows greater maturity, depth, and sensitivity.
For instance, when the Letterkenny Shamrocks Coach calls him out for caring more about hockey player lifestyle than winning—"you're poseurs!"—he and Jonesy put in the effort to get in shape and study the tape, winning both Katy and Coach's approval ("Wingman Wayne"). He objects strongly after he finds the Rookie high on meth, accosting the Skids and then brawling with the natives alongside the Hicks ("A Fuss in the Back Bush"). On the other hand, he continues to womanize, and remains a poor speller ("Letterkenny Spelling Bee").
He had difficulty adjusting to playing senior hockey with the Letterkenny Irish, ostracized from the older teammates. When their old coach returns and dismisses their efforts as a "cakewalk," and berates them for skipping leg day, he admits to Jonesy that he has been playing hurt—not injured, but hurt—and is tempted to skip practice ("Finding Stormy a Stud"). After some soul-searching with Glen, however, he is reinvigorated. He and Jonesy come to lead the league in goals (and PIMs), and they take a leadership role on the team, rebuilding team unity by ridding them of a divisive puck bunny, tillying together, and coaching them at chirping from the bench.
Reilly speaks almost exclusively in hockey lingo and other "jock talk," often riffing extensively with Jonesy. He appears to do so almost unconsciously, using jargon even when speaking with people like the Hicks or Glen.
He and Jonesy befriend Ron and Dax at the gym, praising them for their fine chirping, and later attend Ron and Dax's wedding ("We Don't Fight at Weddings"). At a subsequent conversation, they agree to a "takedown tourney" to see who can bed the most sexual partners ("What Could Be So Urgent?"). Not long after commencing, however, he acknowledges they may be outmatched; the competition ends abruptly when he and Jonesy contract a sexually-transmitted disease ("Different Strokes for Different Folks").
Reilly wears his hair in a long hockey flow. Outside the rink, he usually wears a tank top, board shorts, and flip-flops or trainers, usually accessorized with sunglasses and/or a ballcap. He dips tobacco, and is often seen holding a spitter. When working out in The Basement, he may be seen in a fluorescent green sleeveless T-shirt or a sleeveless hoodie.
After they become assistant coaches for the Letterkenny Shamrockettes, he is most often seen wearing a white V-neck T-shirt and Shamrockettes warmup suit, with a backwards Shamrockettes baseball cap, even wearing this outfit to the Letterkenny Adult Spelling Bee ("Letterkenny Spelling Bee"), to the "bock et biche" in Quebec ("Bock et Biche"), and Wayne's Christmas party ("The Three Wise Men"), though he wears a suit to the championship game.
He drives a late model red Jeep Wrangler, often blasting Kaboom Atomic tracks; he appears to admire Kaboom Atomic not just for his music, but for his flow ("Wingman Wayne").
Reilly's closest and most intense relationship is with his teammate and coaching colleague Jonesy. The two are almost inseparable, whether chirping from the bench, repping at the gym, crushing sandos, or wheeling slams. They even engage in pillow talk via video chat to recount their day, signing off only when the time comes to "aggressively masturbate" ("Wingman Wayne").
They had a polyamorous relationship with Katy for a while. Later, Katy decided to get back together— but only with Reilly ("Bradley Is a Killer"). This drove a wedge between him and Jonesy, and each felt loneliness exacerbated by taunting from the gym rats Dax and Ron ("Never Work a Day in Your Life"). Reilly eventually soured on the relationship, as Katy was making him run errands for her, while Jonesy was off-put by Glen and the Skids' efforts to recruit him to their groups. Ironically, Reilly and Jonesy both felt the need to pretend his life was great to cheer up the other, making the situation even more awkward ("A Fuss at the Golf Course"). Eventually, Reilly rescued Jonesy, and Katy broke up with Reilly so that the two of them could wheel, snipe, celly together again ("Way to a Man's Heart").
They became "accidental tunnel buddies" when they hooked up with each other's "swipy snipies" on Halloween night and early the next morning ("The Haunting of MoDean's II"). They have previously alluded to sharing sexual partners before, however, not just Katy; for example, both took down their student trainer on her kinesiology internship ("Uncle Eddie's Trust").
The Coach has little regard for Reilly at the start, seeing him as more interested in the hockey player lifestyle than in winning games, but things improve after he and Jonesy put in the effort to improve their play for the Shamrocks ("Wingman Wayne").
Reilly and Jonesy struggle in their first year of senior hockey, and when their old Coach is hired as their new bench boss and berates them for skipping leg day, he suffers an identity crisis ("Finding Stormy a Stud"). Returning reinvigorated, however, he and Jonesy come to lead the league in goals (and PIMs), making them the Coach's pride ("Sled Shack").
When the team folds, Coach invites Reilly and Jonesy to be his assistants in coaching the Letterkenny Shamrockettes, giving them the task of fixing team unity ("The Ol' College Try"). He bets on them in the Letterkenny Adult Spelling Bee, but his attempt to fix the bee fails, and they are eliminated ("Letterkenny Spelling Bee"). Nevertheless, he is overjoyed with them when the Shamrockettes win back-to-back-to-back championships ("Back to Back to Back").
When Reilly and Jonesy suffer a personal crisis over their play on the Letterkenny Irish, Glen appears unexpectedly at the hockey arena, he says, "for a normal reason." He takes them out for ice cream and suggests that they take guidance from God, but they are slow on the uptake. Glen, ultimately, cannot understand their motivations and gives up on trying to convert them ("Finding Stormy a Stud").
Reilly and Jonesy are dating Katy simultaneously at the start, affectionately nicknaming her Katy-Kat. Outside her presence, Reilly speaks coarsely about being unfaithful to her when on the road ("Super Soft Birthday"). Still, it matters to him for her to come to games, and when she voices her disappointment with their lack of play time, he and Jonesy work to improve their performance and hustle. Rewarded with more time on the ice and rare approval from the Coach, however, they dislike the attention she draws from Shoresy and the other players, and they ask her not to come to games any more ("Wingman Wayne").
When the Letterkenny Irish finally get a W at the end of the season, Katy indicates that she wants to get back together—but with just one of them: Reilly. This leads to mixed emotions for both, and drives a wedge between the two buddies. While they try to speak encouragingly to each other, the situation remains awkward until Katy breaks up with Reilly, allowing the two of them to resume adventures together.
Reilly and Jonesy struggle to fit in when they first join senior A hockey, receiving contempt and abuse from Barts, Shultzy, Yorkie, Fisky, and Boomtown. After they help rid the team of a puck bunny (Angie), and then become leading scorers on the team, the dynamic changes dramatically, with Reilly and Jonesy becoming de facto captains, admonishing them on everything from shredding the red to trimming their bush. The sole exception is Shoresy, who continues to hurl abuse and sometimes urine at them throughout.
Ron and Dax
Reilly is bewildered when he first encounters Ron and Dax while lifting weights alone at The Basement. Once he is reunited with Jonesy, however, he takes their attention in stride, complimenting their chirping even though "people aren't supposed to enjoy being catcalled." Once Ron and Dax establish that they are interested in otters—and not men built like Reilly and Jonesy— they become buddies ("Way to a Man's Heart"), and are invited to Ronny and Daxy's wedding ("We Don't Fight at Weddings").
Reilly is frequently the target of Shoresy's chirps, many of them sexually explicit references about his mother, often in the showers or when on the toilet. The antagonism between them grows over the years, culminating when Reilly's mother texts him on the night of the Letterkenny Shamrockettes' championship, not to say congratulations, but to ask if he had heard from his friend Shoresy.
Reilly is wary of Tanis, fearing her crew of Natives when the Letterkenny Shamrocks have a game at the Rez ("Rave"). Fearing repercussions from the ban from Letterkenny, he and Jonesy enlist the assistance of the Hicks when they return to the Rez with the Letterkenny Irish ("The Native Flu"). In return, they accompany the Hicks to the Rez, this time in support of Tanis, as she tries to win back the loyalty of Axe and Slash, and they brawl against the degens with the Hicks and the Natives ("Way to a Man's Heart").
Wayne is mostly contemptible of Reilly and all hockey players, and dismissive when Reilly and Jonesy challenge them to fight ("Ain't No Reason to Get Excited") ("Finding Stormy a Stud"). Still, he and the Hicks drink with them after they brawl together on several occasions ("A Fuss in the Back Bush") ("Way to a Man's Heart").
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