Throughout its nine seasons, The Office had some incredible love stories. Fans followed the horrific Michael and Jan saga until that ran its course and saw Michael find his true match in Holly. Viewers also saw Kelly and Ryan's toxic relationship play out in a magnitude of ways, as did Dwight and Angela's romance. And the love story that keeps going round and round is that of Jim and Pam.
However, what if there was another possible romance brewing at Dunder Mifflin that never had the opportunity to grow due to other parties? Looking back, Toby and Pam could have been a thing. He's always had a hidden obsession with her, and she was the one person who had nothing but nice things to say about him. Were these two robbed of a Scranton romance?
Updated on September 28th, 2022, by Lynn Gibbs: The Office fans respect Pam’s relationship with Jim since it was an ongoing storyline throughout the series, but there’s always a small piece of fans who wonder what life would be like for the Scranton branch if Pam went on a few dates with another Dunder Mifflin worker, Toby Flenderson. It was secretly known that Toby had a small crush on Pam, and it was revealed on Toby’s last day of work that Pam always thought Toby was cute. With both characters secretly interested in each other, there was more than one scene where Pam and Toby could have revealed their true feelings for one another.
Pam Would Choose Toby In The Game Of "Who In The Office"
In the episode 'The Fire,' the office is huddled in the parking lot after a fire breaks out in the Dunder Mifflin kitchen. To pass the time, they start asking each other questions. When the question of "who would you sleep with in the office?" comes up, the answers were mixed.
Michael said he would sleep with Ryan; Kelly and Phyllis said they would sleep with Jim; Jim said he would sleep with Michael; Roy chose to sleep with Angela over his fiancé Pam; and Pam had two answers: Oscar and—drum roll, please—Toby! It wasn't the best quote on love, but it was a choice.
Toby Wins Pam The Duck
When the office went over to Poor Richard's for a drink, Pam notes how cute the duck in the claw game is. She looks longingly at it before sitting down with the rest of the office. The camera then sees Toby looking at the duck and decides to try and win it for her. Although Toby didn't use a pick-up line on Pam, his glance said it all.
By the end of the episode, Toby gives the duck to Pam as a gift, and although she looks happy, she tells him to give it to his daughter instead. Things get even more twisted when Pam asks where he had been all night because she was "looking forward" to hanging out with him.
He Gets Visibly Upset When He Can't Attend Her Art Show
Between Pam's on-and-off relationship with Roy, she focused her efforts on her art and was pleased with her first art show. Viewers could tell this moment meant a lot to Pam, and she really needed the support from friends.
As she's seen telling Toby about the art show, he becomes visibly upset because his daughter's play is on the same night. She tells him not to worry about it, but he considers missing his daughter's performance just to support Pam. He chooses his daughter in the end, but this was a very telling scene. Toby is probably the only co-worker who would take a closer look at Pam's art and appreciate her talent.
The Look On His Face When He Lends Pam His Sunscreen For Beach Day
'Beach Games' was a huge episode for Pam. It was a turning point for her as a person. When Michael decides to host a day of games at the beach, everyone is excited about the opportunity to be out in the sun. However, Michael makes Toby stay behind to take care of the phones.
As he's lending his sunscreen to Pam, she thanks him because she's wearing a two-piece and forgot her own sunblock. The look on Toby's face said it all: he was missing a day of fun in the sun with a newly single Pam to answer phones at Dunder Mifflin. For Toby, this made Michael one of the more annoying characters.
Toby Tries To Reprimand Jim & Pam For Public Affection In The Office
The stars aligned when Jim and Pam decided to put their pride aside and date. They kept their new romance a secret from the office for quite some time before one subtle kiss in the break room spilled the beans.
While Toby was at his desk, he sees Pam give Jim a small kiss on the cheek before heading back to her desk. Annoyed that Pam was dating someone else in the office, Toby wrote an office-wide memo about public affection in the workplace. Pam and Jim thought it was Toby's coy way of congratulating them, but it was serious — he didn't want to see Pam and Jim together. Regardless of Toby's crush, it was one of the better Jim and Pam episodes.
The Knee Graze Seen Around The Globe
When Dunder Mifflin stayed late to work one night, Michael forgot to tell security. The parking lot gates were locked and the workers had no possible way of leaving the premises without someone unlocking the gate. They all waited in the office building's lobby while exchanging stories when Toby cracked a joke.
Pam began to laugh and Toby put his hand on her knee as she did. After lingering for far too long, Jim and Pam realized how weird it was, and the lobby fell silent. Toby was so embarrassed by his actions that he climbed the fence and ran home. It was one of The Office's more cringiest episodes.
When Pam's Missing From The Company Picture
After Toby makes the bizarre announcement that he's quitting Dunder Mifflin and moving to Costa Rica to start a new life, Pam gifts him a picture of the entire office.
Toby immediately scans the photo for Pam's face and can't find it. He mentions her absence, and she says that she's the one who took the picture, that's why she wasn't in it. To make things even weirder between the two, Toby asks her if they can take a picture together but no one in the office had a camera. Instead of giving in, he leaves work to get a camera and comes back later for the picture.
Pam's Offended By Michael's Going-Away Gift For Toby
Besides Michael, Ryan, and sometimes Angela, Pam is nice to everyone in the office. (She pulls pranks on Dwight, but she's not necessarily mean to him.) Her sweetness towards Toby on his last day at work isn't strange, but what was surprising is how she reacted in his exit meeting.
As Michael is getting ready to tell Toby how much he despises him, Toby opens up his "gift" from Michael, which was a rock that said, "Suck on this!" Pam was offended by Michael's rude going-away gift and spun the story around so that Michael had to give Toby his expensive watch — a notion that Toby appreciated. Pam's kindness was one of her better traits, especially when directed to Toby
Pam Says She'll Miss Toby When He Quits Dunder Mifflin
Also in 'Goodbye Toby,' Pam tells the camera crew how much she'll miss Toby. "I'm going to miss Toby," she says. "He has a nice, calming presence in the office." Toby was the most logical person at Dunder Mifflin, but it's hard to tell if his presence would be missed by the office.
Towards the end of her interview, Pam drops a bomb and says "Don't tell him I said this, but I always thought he was kinda cute." By this point, Pam was already deeply in love with Jim but were Pam and Toby an opportunity missed?
When They Danced At Angela And Dwight's Wedding
When season 9 rolled around, Pam and Jim's relationship timeline showed them married and the parents of two children. They had their ups and downs but came out on top. So when viewers saw Pam and Toby dancing at Angela and Dwight's wedding, it was clear that it was platonic. But was it?
Toby was crying uncontrollably when dancing with Pam, and when she asked him what was wrong, he just said, "everything." Was slow dancing with Pam a moment of a lifetime for Toby, and now it was too late to act on his feelings?