Erica is having a great time on her date with a guy, when her cellphone rings. It's Ethan with her emergency call in case she wants to get out of it. She tells him it's going great. The guy, Mike invites her into his apartment for a night cap. She likes the look of his apartment (except for the sink full of dirty dishes), and he shows her his Kenyan masks. Upon closer inspection though, it's made in Taiwan. After a short kissing session, Erica discomfort gets the better of her and leaves.
"The first date is like an open house. The pictures look great. The dimensions are good. And as you stand on the threshold, you think: Could this be it? Could this be the one? You open the door full of anticipation. You walk in and then you start to notice the details. The cracks in the wall. The weird little quirks and then you think: No, this isn't for me."
Ethan and Erica are playing Wii tennis while she explains what was wrong with last night's date. While she's distracted, Ethan wins the match, but asks if she wants a rematch. Erica would but promised Judith that she would help her with the high school reunion decoration, a night to which she is not looking forward.
During the preparations, Judith and Erica recount stories about other people, particularly those they didn't like. Speaking of which, Erica's now ex-friend, Katie was approaching; something that Judith forgot to mention. Whoops.
Katie boasts about her recent promotion and her husband. Erica reluctantly admits she's unemployed at the moment. However, after having quite enough of Katie's condescending voice and assumption, she lies about having a long term boyfriend. Katie is surprised, and mentions that Zack will be the reunion photographer. Judith admits that she forgot to mention that too. Katie sees that she's said enough and goes to buy her reunion ticket. Once she is out of earshot, Judith asks Erica, "What the hell are you doing?" Erica doesn't know.
Later, on the streets of downtown Toronto, Ethan asks Erica why she told Katie she had a boyfriend. Erica couldn't stand Katie's assumption of her singleness. Being her closest male friend, Erica convinces Ethan to pretend to be her boyfriend for the night. Ethan jokes about what job he will tell he has. She tells him to just be normal, but to inform Judith and Jenny about the plan since they know him from university. For now, she needs to get to her interview.
At the interview, she tells the manager than she is a big fiction fan, despite applying for a job at a publisher that specialises in non-fiction. She understands that the job is clerical in nature, but is willing to go for it. He is amused and tells her he will contact her in a few days.
It's the night of the reunion. Before Erica and Ethan enter, Erica, still extremely nervous, wants a signal for Ethan so that they can leave if anything goes wrong with her fake boyfriend plan. Erica decides on a shake of her hair.
The first person they see though is Zack. This and his camera bring back painful memories of him taking her virginity. She excuses herself to go to the bathroom. She pauses before she gets there, and bumps into Alex Berlin, her old chemistry lab partner. He's just barely recognisable to her, as he has gotten a lot more handsome, and much less shy. There's clearly some chemistry between the two.
Erica heads back to the party. Ethan is talking to Katie, Jenny, and Judith. He lies to Katie and says he's a doctor. Katie is intrigued and manoeuvers him to a nearby table so they can talk alone. Ethan is spinning his stories, but one story seems a lot like an episode from House. Ethan says they got the idea from a patient case of his. Erica hears enough of it, and signals Ethan to stop. After he sees it, Erica steps out to actually go to the bathroom. She instead turns up in Dr. Tom's office.
Dr. Tom is, of course, completely aware of the situation. He wants to talk about one of her regrets on the list. "Losing her virginity to Zack Creed." Erica reluctantly recounts how she had just started going out with Zack, the hottest guy in the grade. During a trip to Muskoka, (a popular camping destination in Ontario), with their graduating She knew they would be separated soon due to graduation and him moving. The sex was horrible and painful, but what was worse was the video camera that Zack had set up beforehand, without Erica's knowledge, to capture the entire scene and show to all his friends.
Erica has questioned her own judgment of guys ever since, and believes it has crippled her ability to be in a relationship. She looks for faults right away. Though she claims otherwise, Dr. Tom observes that Erica does not seem over the incident at all. He asks her what she would do differently when she goes back. She explains that she will not have sex with him, and will tell him off for revenge sake.
Erica is sent back to 1994. Unfortunately, she supposed to be in the middle of driving her, Jenny, Judith, and Katie to the Muskoka camp site. The disorientation of time travel though nearly lands them in an accident.
After parking, she explains that she was momentarily distracted. Her friends seems to know her original plan to have sex with Zack, and tease her that this must be the reason. Erica tells them that she's having second thoughts about it now. They don't believe her since just two hours previous, she had been gushing about how perfect it was going to be. With what she knows now, Erica's changed her mind.
At that moment, Zack pulls up in his ride, explaining that he has it all planned, including an entire box of condoms. Erica remarks, "That's really optimist of you." Erica starts to explain her change of heart, but instead decides on another course of action. To Zack, she feigns interest. While gathering firewood for the camp fire with Judith, Erica tells her that it doesn't feel right. Judith thinks she's scared Erica with the story about her first time. Erica assures her that it wasn't anything she did. Just then, a broken twig falls on Erica's head. The girls look up to see Alex watching on them. He climbs down to apologise, but can't get the words out. Jenny arrives to check on their progress. Erica tells Judith and Jenny to go on ahead, so she can talk with the younger Alex.
She finds out he was in the tree writing poetry. They take a walk through the woods, with Erica trying to persuade him to read one of his poems. Alex relents eventually. Afterwards, she compliments him, but they are interrupted by Zack, who tells him to get lost. He's about to start the fire and wants Erica to come watch him.
Knowing that the time is soon upon them, Erica looks a bit apprehensive. Zack lead them to the spot that he has planned. Zack tries to kiss her, but Erica convinces him to take off his clothes and close his eyes first. Stripping down, he lays down near on the blanket by the lake and closes his eyes. Erica gets the camera and starts pointing it at him. He covers himself with his hands. Erica chews him out and leaves.
Walking by the lake, she spots Dr. Tom fishing. Erica remarks that just because one guy hurt her doesn't mean they all will. Dr. Tom reminds her that it's still never easy. "There's a difference between knowing the path, and walking the path." Erica is puzzled that he quoted from "The Matrix".
Returning to the camp that night, the rest of the are avoiding her. Jenny and Judith tell her it's because Zack spread a rumour that she has "Syphil-ass" or syphilis of the ass. She stomps off to find Zack who is now kissing her friend Katie. Zack is very pleased with himself. Alex comes to defend her, telling him that there's no such thing as "syphil-ass" and insults him. They start to brawl and end up in the water. Erica pulls Alex away.
Away from the rest of the group, Alex confesses his crush on Erica, but didn't know how to express it until now. Uncharistically, he proceeds to kiss her and even he's shocked he did it. Erica starts to remove her clothes and leads them down to a canoe where they proceed to have sex. Mid-orgasm though, she's transported back to the present.
Still feeling the effects, she exits the boys' dressing room where reunion outside the door heard her screams of passion. Alex rushes over concerned, but she awkwardly dismisses his fears. The tension is palpable, and Alex jokes that he still has marks on his back from the canoe. Erica laughs. They wonder what if their futures would have been different if they hadn't separated to go to university. Erica then spots Ethan, excuses herself and pulls Ethan to the bar. She tells him that Alex might be the one so his job is done, so he needs to leave.
Ethan passes by the photos that Zack has taken for the night. Zack asks him if he wants the picture of Ethan and Erica. Ethan explains that they just broke up. Zack muses that he knows the feeling as well, and that Erica was the only one that evr blew him off. Zack says that Erica is someone worth fighting for. Ethan explains that it's what she wanted.
Back at the party, Erica and Alex seem to be hitting it off... until she starts talking about Maglev trains and toy train sets. Erica's alarm bells start to go off again.
Jenny, Judith, and Katie are dancing and joking about old times, when Katie ask where Erica is. Jenny, unfortunately, tells her that she's talking with Alex Berlin. Katie finds that strange since Erica's supposedly with Ethan. Angry that she was lied to, Katie goes to confront Erica.
Alex is going on about his trains, and Erica is bored out of her mind. Katie shows up as an unlikely saviour. Katie just wants to expose Erica as a fraud though. Erica tries to explain to Alex, but he rebuffs her, telling that he just left a long term relationship with a woman who was cheating on him. He refuses to deal with any more drama, and leaves. Erica is confused. She wasn't happy, but she hadn't wanted him leave her either.
Walking home, she stops by a variety store for ice cream as conciliatory gesture. On the way, she sees Dr. Tom and stops by to chat. She admits that he was right about the Matrix thing. This time she was on the receiving end, and she doesn't like feeling judged. She was hoping to stop needing to pick guys apart. Dr. Tom tells her it's the fear of the next step that holds her back. She needs to learn to take the leap, to choose to confront her fear and see what comes. Then he tells her that her ice cream is melting. He whistles her a cab (in a city where that doesn't usually work).
In the cab, her cellphone rings. It's the publishing company with a voice message. She got the job as an assistant!
At Ethan apartment, Erica apologises for her behaviour. Ethan explains he's a good actor, but he doesn't really want to start dating again. He feels like he's damaged goods. Erica assures him that he's a great guy. After a tense moment, they share a slow kiss. They look at each other, as if for the first time.