10 Girls Toby May Have Been With (Different Than Pam)
Toby Flenderson is Dunder Mifflin Scranton’s resident HR consultant. It is an ongoing bit all through The Workplace‘s 9 seasons that Michael Scott loathes Toby and forces him to work within the annex with Kelly so he does not should see him on daily basis. As a result of Toby works in HR, Michael thinks Toby sucks the enjoyable from every little thing.
However deep down, Toby is an extremely good and healthful man. He is a single father who’s simply attempting to catch a break, and even discover love. He subtly confirmed indicators of crushing on Pam, however his emotions by no means got here to fruition as a result of he was too shy to voice them. If he confirmed a bit extra braveness, there have been different ladies he might have had a shot with.
10 Erin Hannon
Erin Hannon is without doubt one of the nicest ladies within the workplace. She’s a tad naïve however has an ideal coronary heart and loves individuals for who they’re — simply not Gabe.
Toby is a candy, mature man, so why would not Erin discover herself drawn to him? If she wasn’t in love with Andy for therefore a few years, followers can see Toby and Erin occurring just a few smitten dates with one another. Their relationship in all probability would not final greater than a month (Erin’s a bit too younger for him) however just a few dates are simply doable for these two. (Erin must hold it a secret from Michael, although…)
9 Pam’s Good friend, Julie
Within the episode “Completely happy Hour,” Pam is dying to exit and be with mates after being residence with the youngsters all day. She finally ends up inviting her pal Julie as a possible date for Michael. Michael and Julie had been shockingly hitting it off earlier than he realized he was being arrange and reworked into one other particular person.
If Toby was at completely satisfied hour and put his crush for Pam apart, he and Julie might have been good. She was obsessed with goofiness and did not thoughts that Michael was a bit shy. She most positively would have reacted the identical to somebody like Toby.
8 Kelly Kapoor
Are Kelly and Toby endgame? No. Would they last more than a month? In all probability not. Nonetheless, these two might have examined the courting waters after they each discovered themselves alone on Valentine’s Day or a birthday.
Kelly loves children and Toby is a single father; Kelly likes to be adored and all Toby needs to do is be in love once more. These two might have stuffed the void for a short while — particularly since they labored in shut quarters collectively. Toby has listened to each frustration and completely satisfied second in Kelly’s life for years within the annex. He’d make a beautiful boyfriend for her till he could not sustain anymore.
7 Nellie Bertram
Nellie did not come to Dunder Mifflin till season 8, however it was apparent Toby was fairly taken by her. He was speechless when he met her and by chance referred to as himself Tony. The 2 continued to develop nearer when Toby informed Nellie concerning the Scranton Strangler case. They even kissed within the kitchen!
Nellie wasn’t anticipating this random fling with Toby however it simply type of occurred. If she gave in to her emotions, these two might have been good collectively. There was one thing about Nellie that made Toby bolder, extra assured. He wanted a robust but empathetic girl like her. Plus, she beloved children and wished extra of her personal. Toby might have been that man if she let it to occur.
6 Pam’s Landlord, Margaret
When Michael breaks up with Jan, he is prepared for a rebound relationship. He begs and pleads together with his workers to set him up with somebody they know. And whereas others set him up with Wendy from Wendy’s, Pam thought it was a good suggestion to set him up along with her landlord, Margaret.
Margaret was candy and an ideal listener, however she was additionally a bit shy and timid. She and Michael proved to be an terrible match, although it is attainable to see her with somebody endearing like Toby.
5 Holly Flax
Holly Flax is Michael’s longtime love and future spouse. These two had plain chemistry and a language that solely they may perceive. However in an alternate universe the place Michael chooses Jan and her child over Holly, why would not Holly give Toby a shot? Though Toby was leaving the workplace, he would have stayed in Scranton for a blossoming relationship. Holly is an effective listener, a logical particular person, and she or he likes to have enjoyable outdoors of labor — similar to Toby.
4 Angela Martin
Angela is imply, judgmental, and close-minded. However as time goes on, she loosens up. She’s seen hanging out along with her co-workers an increasing number of, and never rolling her eyes a lot.
If she by no means ended up with Dwight and he received married to Esther, Angela might have leaned on Toby for help. He does have a counseling diploma and is a licensed therapist of kinds. He might have recommended Angela again to well being however shaped a more in-depth bond whereas doing it. This might have led them to espresso dates or lunches collectively earlier than they even realized there is a spark.
3 Helene Beesly
If it wasn’t imply to be with Pam, perhaps Toby might have ended up along with her mom? Followers know simply how a lot Pam hated Michael courting Helene, however Toby is not Michael. Toby is way extra accountable and grounded; one thing Pam can get behind. It might have been bizarre for her co-worker and her mother courting however it could have been extra accepted than Helene and Michael.
In season 5’s “Blood Drive,” Michael throws a Valentine’s Day mixer on the workplace. He met a girl within the parking zone that labored on the workplace park and was looking for a option to work together along with her once more, so he threw a mixer.
Sadly, the 2 by no means noticed one another once more, however Kevin did meet Lynn on the occasion. It was an prompt connection and the 2 began courting shortly after. Nonetheless, Lynn and Toby might have made a pleasant couple too. Each characters are soft-spoken and a bit nervous, however they may have warmed up to one another and began one thing candy — particularly whereas working in the identical advanced.
1 Isabel Poreba
Isabel is Pam’s cousin. Viewers first meet her at Pam and Jim’s marriage ceremony, however she pops up spontaneously all through the season due to her odd relationship with Dwight. Nonetheless, when Dwight pushed Isabela method on the ceremony, what if she landed within the arms of Toby? She might have used him to make Dwight jealous, however then realized she had emotions for this thriller man. And as soon as once more, Isabel is a member of Pam’s household, so Pam might have put in a very good phrase for him.
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