Characters / The Trading Post

Characters appearing in The Trading Post, in order of appearance... beware spoilers!

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Narrator Characters

    Class of 2006 

Arthur "Art" Milligan/Elizabeth "Liz" Lee/Penelope "Penny" Lincoln

The one who started it all. Art was a California-based freelance reporter booked to stay at the Inn during the local Beerfest. He had an inquisitive and capable personality, which served him well when he found himself transformed: Very rational and inquisitive, it was his observations that formed most of what readers learned about the Inn to begin with. His skills served him in plotting his return to the Inn, theorizing (correctly) that if he returned to the Inn immediately after the person in his old body, he would be transformed back.

From September until the Spring, he had to endure life in the body of Elizabeth Lee, a Boston cinema manager and former aspiring actress. Some of the problems he inherited from Liz included her family's tendency to speak Korean and the affair she was carrying on with co-worker Stewart while living with her longtime boyfriend Ray. Whoops.

When he finally did return to the Inn, he had been double-crossed. The "New Art" got cold feet and decided to send Penelope Lincoln in his place (along with her boyfriend, RJ.) Forced to confront the reality that he would never return to his original life, he transitioned from Penny's job as an on-air sports reporter (in California) to a print journalist (in Boston.)

Jake Matthews/Ashlyn Shelley

Originally an online acquaintance of Art's, and a native of Dallas, he decided to come to Maine to take a break from his workaholic lifestyle. Unfortunately, he didn't realize exactly how long that break would be. He became Ashlyn Shelley, an unemployed model/actress/waitress in Boston. The new Jake was a lot more upfront than the new Art — about midway through the first year, he admitted he was doing too good a job running Jake's graphic design company to just hand the life back, and "Ashlyn" became the first character to have to confront the reality of never going back. From that day on, "Jake" became a different person altogether.

Through Ashlyn's eyes, we see a lot more of the mental effects of the Inn. While Art was very rational and pragmatic about the change — engaging in sex to maintain continuity with both Ray and Stewart, and not seeming to derive much pleasure from it — Ashlyn acknowledges her body's needs and desires are different from her previous one, and accepts it as she dates and attempts to find her identity.

Jeff Miller/Brianna Adamson

A recent high school grad pleased to finally be out on his own... until he wakes up as a teenage girl.

Dex Langan

Mark Lange/Ginessa

Vinny De Santis/Sarah Hansen

Drew Dawson/Daphne/RJ

Returned at the same time as Arthur, winding up in the body of Penny's boyfriend RJ. He was relieved to return to a male existence (the blog's first instance of averting the first law.) Art/Penny's tendency to maintain status quo, as well as their familiarity with each other, led to a brief fling between the her and the male Drew/RJ, but there was no feeling there and Art left for Boston.

    Class of 2007 


Trip, an IT guy in his own life, had the ordeal of staying in the same room previously occupied by his cousin, Kat, leading to some awkwardness upon his transformation into her.

Darren Bridger/Jamie

Was due to ship out for service in the Navy before his stay. Instead, he had to live in New York City as food critic Jamie, certainly a much less rugged lifestyle than he was used to. circumstances kept him/her from returning, and she was last seen in conversation with Todd, still resiting adapting to the transformation, nearly two years after her stay.

    Class of 2008 

Todd Casey/Anne-Marie Adkisson

A Canadian sometime-musician and sometime-journalist when he found his way to the Inn. He had been traveling all summer after dropping out of University, growing frustrated with his job, and having a catastrophic break-up with his girlfriend Alia. Toward the end of the Summer, he called her to reconcile, and she offered him her parents' canceled reservation at the Inn, not knowing of its curse.

When he woke up, he was in the body of Anne-Marie Adkisson, an upper-class housewife in Connecticut. Todd spent the year coping with suburban boredom, frustrating family relations and growing as a person. He did successfully return to the Inn, but it was a rough road back and something of a Pyrrhic victory, given who was also there...

Bryan Lewis/Ellie Mc Clay

Todd's best friend and stepcousin, a rather easygoing fellow who was along for the trip when they got caught at the Inn. He became Ellie, Anne-Marie's niece, a high school freshman. Initially he took the transformation in stride, having lived a rather transitory lifestyle anyway, but began to collapse under the pressure of the modern teen girl's lifestyle. This was certainly not helped by coping with Ellie's burgeoning sexuality. While Todd, like Art before him, coupled with Anne-Marie's husband out of a sense of duty, Bry was left to his own devices. Whether because of his own tastes or perhaps Ellie's young hormones, Bry was openly attracted to females. He fell for Leanne, a drummer in a garage band he joined as Ellie, but Leanne, an older girl than Ellie, saw her as just a kid and not ready for a serious lesbian relationship. This triggered an emotional breakdown that threatened Bryan's freedom to return to the inn, worsening tensions between Ellie's mother and her sister-in-law, Anne-Marie (Todd.)


A male Olympic-caliber swimmer who became a rather less athletic female.

    Class of 2009 

Alia Frye/Roberto "Rob" Garcia

In order for Todd to return to his own body, the "new Todd" had to go back to Maine. Frustrated by "Todd's" secretive nature, unaware of the Inn's secret, and apparently impatient, Alia elected to follow him there, only to arrive a week late... in time to meet "Anne-Marie." Todd considered leaving the Inn before the transformation, in hopes that it would prevent her from learning the truth (and undergoing the transformation herself) but it was not to be, and Alia became Rob, a high school English teacher from Philadelphia, at the same time as Todd regained his own body.

John Henry "Cliff" Clifford/Victoria "Tori" Pearce

When Alia was at the Inn, she asked one visitor with an ocean view to switch rooms. He brushed her off rudely, (taking the opportunity to invite her instead to stay in the room with him.) Because of that, Alia stayed in her room and became Rob while Cliff became Tori, a 22-year-old hairdresser from Philadelphia. Had he simply let her have the room, the rest of his life would have turned out differently.

Notably, in his original life, Cliff was unlucky with love, and despite having had a long-term (devout Christian) girlfriend years earlier, was a virgin at nearly 30. He did not enjoy having his equipment being replaced before even having a chance to enjoy it. However, like Ashlyn before him, he found himself adapting rather than rebelling against biology.


Greg, a hotel manager from Chicago, woke up as his fiancee's best friend Priya. This in and of itself would be awkward enough if the woman in his old body (Dee) had not fallen into an affair with a co-worker at his old job, causing her to break off his relationship and commandeering his life for good.

Sullen and with no place to go, Greg spent a year in her life, as an older middle-aged woman living alone, before returning to the Inn once more to become Alexis, a lesbian from Vermont. Ultimately, Greg seems resigned to his fate to be a "traveler," someone who repeatedly returns to the inn without any intention of getting a specific body.