Toby Flenderson, the human resources employee at Dunder Mifflin Scranton branch harbored strong feelings for Pam Beesly, the receptionist who eventually became a saleswoman and ultimately became the office administrator. Between Michael Scott's constant harassment and his personal problems, not once did Toby step back from showing his unrequited love for Pam.

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From lending Pam sunscreen to almost ditching his daughter's play for her art show, Paul Lieberstein's lovelorn HR representative, Toby did it all on The Office.

10 Almost Asked Pam Out

The Office: Toby was too shy to ask Pam out

Toby wasted no time in walking up to the newly-single Pam Beesly in "The Convention." Pam would have agreed to go out with Toby considering she found him cute. If only the man could have had the courage to ask her out!

It was painful to watch Toby stand dumbfounded at reception unable to able to say much besides, "I wanted to ask if you wanted..."

Toby's words were devoid of feelings but his face certainly wasn't!

9 Won Pam A Plush Duck At Poor Richard's

The Office Toby spent all night getting the duck for Pam

Out of all the ways co-workers tried to woo Pam on The Office, Toby winning her the plush duck in a claw game was the most diligent.

In "Cocktails," the gang headed to Poor Richard's for happy hour after work where Pam noticed the duck sitting in the toy chest. Toby thought gifting her this stuffed animal would automatically convey his feelings. He spent the whole night trying to win Pam the duck and in the end didn't dare to say anything beyond, "Here."

Of course, Pam thought the cute duck would make a better toy for Toby's daughter, Sasha.

8 Reconsidered Attending Sasha's Play For Pam's Art Show

The Office Toby almost ditched his daughters play to attend Pam's art show

Pam was visibly sad her co-workers, but more importantly, her best friend, Jim ditched her art show. Toby would have made it, had his daughter, Sasha's play not been scheduled the same night.

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Not only did Toby reconsider watching Sasha's videotaped play to "support local [Pam's] art," he also badmouthed it. "And what they do is not art," Toby disappointingly said, regretting the two events coincided.

7 Lent Pam His Sunblock

The Office Toby was upset upon hearing Pam was wearing a two piece

Toby was totally psyched to go to the beach in "Beach Games." Decked in beachwear with an SPF 30 sunblock in hand, he couldn't wait to get going. The boss, Michael Scott, however, refused to allow him to attend the outing stating someone had to stay back at the office.

As everyone was leaving, Toby was happy to ask if Pam, of all people, needed his sunscreen. He was also saddened to learn Pam was going to be wearing a two-piece at the beach.

6 Served The Entire Office With PDA Memos

The Office Toby made the PDA memo

Toby Flenderson was an utterly irresponsible HR representative. For starters, he could have handled the office affairs in an efficient manner than being a mute spectator to most of Michael Scott's antics. Toby's inactive approach was well demonstrated in "Conflict Resolution" where everyone agreed he merely listened to their office problems.

However, when in "Dunder Mifflin Infinity," Toby saw Pam embrace Jim, he immediately distributed PDA memos reminding everyone about the company etiquette involving PDA.

Moreover, Toby lied about employees complaining about public embraces, while in reality, he was the only one rife with sadness upon seeing Pam and Jim together.

5 Lived In Denial To Cope With Pam's Relationship

The Office Toby denied Jim and Pam to sign relationship documents

Toby's odd and unprofessional behavior following the PDA memo distribution was self-explanatory. First, he outed Jim and Pam in the hopes of scaring them. When that didn't quite pan out as he'd thought, he relied on a carefully regimented program of denial.

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When Pam and Jim informed Toby they were ready to sign relationship acknowledgments that would serve them legally and officially, the latter dismissed them saying those were only for serious relationships, not casual things. He asked them to wait it out, prompting Jim to say, "What?"

4 Jeopardized Jim's Job

The Office Toby complained to Ryan about Jim

In "Did I Stutter," Toby filed a complaint to Ryan Howard about Jim supposedly having an incessant nonchalant work attitude. While he alerted Ryan about Jim goofing around with Dwight and hanging out at reception, the truth is, he only cared about the latter. As a result, Ryan, in Toby's presence, let Jim off with a warning.

If Toby really cared, he could have addressed Jim's work performance personally. He tried to jeopardize Jim's job so he could have a chance with Pam. Toby made his obsessive love disorder apparent by saying, "I'd say all the goofing around at Pam's desk, and, and hanging out with Pam, has finally caught up to him… w-with Pam."

3 Knew Pam's First Celebrity Crush

The Office Toby knew Pam's first celebrity crush

Toby's affection for Pam was obvious in a very subtle way, but not around the time he shouted out Pam's first celebrity crush. After attending Roy's wedding, Jim and Pam felt they knew everything about each other, so they took a fun couples quiz along with Angela, Oscar, Kevin, Phyllis, and Toby.

When Phyllis asked who Pam's first celebrity crush was, Toby rightly muttered John Stamos to himself. Pam quickly added John Stamos was temporary and that she'd moved on to someone else. At this point, Toby couldn't keep himself from saying Johnny Depp's name out loud.

2 Happy To Learn Jim And Pam Were Late For Their Wedding

The Office Toby was excited to hear Jim and Pam were missing from the wedding

Before Jim and Pam's wedding ceremony started, Toby slept on a church bench like a forlorn lover who couldn't bear to see the girl he loved marry someone else. The moment he learned from Dwight Jim and Pam were missing for an hour, he got up and spoke excitedly to the camera crew.

"Well, I guess this wedding is not gonna happen. Wonder if this is it for them," said Toby in a brief moment of excitement as Jim and Pam walked past him.

1 Absent From The Wedding Dance

Everyone from Dunder Mifflin except Toby does a dance down the aisle

Everyone from Dunder Mifflin except for Toby voluntarily took part in Jim and Pam's wedding. They looked happy for the couple as they danced down the church aisle to Chris Brown's Forever. 

Toby's excitement at the thought of Pam not actually marrying Jim was short-lived when he saw the couple back at the church. He was visibly upset and absent from the wedding dance that even the grumpy Stanley Hudson and the outsider Bob Vance were a part of!

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