Toby Flenderson is Dunder Mifflin Scranton’s resident HR representative. It’s an ongoing bit throughout The Office‘s nine seasons that Michael Scott loathes Toby and forces him to work in the annex with Kelly so he doesn’t have to see him every day. Because Toby works in HR, Michael thinks Toby sucks the fun from everything.
But deep down, Toby is an incredibly nice and wholesome man. He’s a single father who’s just trying to catch a break, and even find love. He subtly showed signs of crushing on Pam, but his feelings never came to fruition because he was too shy to voice them. If he showed a little more courage, there were other women he could have had a shot with.
10 Erin Hannon
Erin Hannon is one of the nicest women in the office. She’s a tad naïve but has a great heart and loves people for who they are — just not Gabe.
Toby is a sweet, mature man, so why wouldn’t Erin find herself attracted to him? If she wasn’t in love with Andy for so many years, fans can see Toby and Erin going on a few smitten dates with each other. Their relationship probably wouldn’t last more than a month (Erin’s a bit too young for him) but a few dates are easily doable for these two. (Erin would have to keep it a secret from Michael, though…)
9 Pam’s Friend, Julie
In the episode “Happy Hour,” Pam is dying to go out and be with friends after being home with the kids all day. She ends up inviting her friend Julie as a potential date for Michael. Michael and Julie were shockingly hitting it off before he realized he was being set up and transformed into another person.
If Toby was at happy hour and put his crush for Pam aside, he and Julie could have been perfect. She was smitten by goofiness and didn’t mind that Michael was a little shy. She most definitely would have reacted the same to someone like Toby.
8 Kelly Kapoor
Are Kelly and Toby endgame? No. Would they last longer than a month? Probably not. However, these two could have tested the dating waters when they both found themselves alone on Valentine’s Day or a birthday.
Kelly loves kids and Toby is a single father; Kelly loves to be adored and all Toby wants to do is be in love again. These two could have filled the void for a short time — especially since they worked in close quarters together. Toby has listened to every frustration and happy moment in Kelly’s life for years in the annex. He’d make a lovely boyfriend for her until he couldn’t keep up anymore.
7 Nellie Bertram
Nellie didn’t come to Dunder Mifflin until season 8, but it was obvious Toby was quite taken by her. He was speechless when he met her and accidentally called himself Tony. The two continued to grow closer when Toby told Nellie about the Scranton Strangler case. They even kissed in the kitchen!
Nellie wasn’t expecting this random fling with Toby but it just kind of happened. If she gave in to her feelings, these two could have been perfect together. There was something about Nellie that made Toby bolder, more confident. He needed a strong yet empathetic woman like her. Plus, she loved kids and wanted more of her own. Toby could have been that guy if she let it to happen.
6 Pam’s Landlord, Margaret
When Michael breaks up with Jan, he’s ready for a rebound relationship. He begs and pleads with his employees to set him up with someone they know. And while others set him up with Wendy from Wendy’s, Pam thought it was a good idea to set him up with her landlord, Margaret.
Margaret was sweet and a great listener, but she was also a little shy and timid. She and Michael proved to be an awful match, though it’s possible to see her with someone endearing like Toby.
5 Holly Flax
Holly Flax is Michael’s longtime love and future wife. These two had undeniable chemistry and a language that only they could understand. But in an alternate universe where Michael chooses Jan and her baby over Holly, why wouldn’t Holly give Toby a shot? Although Toby was leaving the office, he would have stayed in Scranton for a blossoming relationship. Holly is a good listener, a logical person, and she likes to have fun outside of work — just like Toby.
4 Angela Martin
Angela is mean, judgmental, and close-minded. But as time goes on, she loosens up. She’s seen hanging out with her co-workers more and more, and not rolling her eyes so much.
If she never ended up with Dwight and he got married to Esther, Angela could have leaned on Toby for support. He does have a counseling degree and is a certified therapist of sorts. He could have counseled Angela back to health but formed a closer bond while doing it. This could have led them to coffee dates or lunches together before they even realized there’s a spark.
3 Helene Beesly
If it wasn’t mean to be with Pam, maybe Toby could have ended up with her mother? Fans know just how much Pam hated Michael dating Helene, but Toby isn’t Michael. Toby is far more responsible and level-headed; something Pam can get behind. It would have been weird for her co-worker and her mom dating but it would have been more accepted than Helene and Michael.
In season 5’s “Blood Drive,” Michael throws a Valentine’s Day mixer at the office. He met a woman in the parking lot that worked at the office park and was trying to find a way to interact with her again, so he threw a mixer.
Sadly, the two never saw each other again, but Kevin did meet Lynn at the event. It was an instant connection and the two started dating shortly after. However, Lynn and Toby could have made a nice couple too. Both characters are soft-spoken and a little nervous, but they could have warmed up to each other and started something sweet — especially while working in the same complex.
1 Isabel Poreba
Isabel is Pam’s cousin. Viewers first meet her at Pam and Jim’s wedding, but she pops up spontaneously throughout the season because of her odd relationship with Dwight. However, when Dwight pushed Isabela way at the ceremony, what if she landed in the arms of Toby? She could have used him to make Dwight jealous, but then realized she had feelings for this mystery man. And once again, Isabel is a member of Pam’s family, so Pam could have put in a good word for him.
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