There's No Way You Can Get 100% On This The Office Relationships Quiz

Historians centuries from now may look to NBC's the Office as a shining example of 21st century American sitcoms. The show can definitely help future generations understand our love for comedy, pranks, friendships and relationships.

The Office, developed from the original UK series on BBC, by Greg Daniels, covers all aspects of American life in hilariously relatable and unrelatable ways. As we follow Dunder Mifflin employees at the company's office in Scranton, we learn about their lives, including their failures and successes. As we follow the lives of the office's many employees, we undoubtedly get a glimpse into their romantic histories.

Love on the Office can be complicated, especially since many of the characters are extremely complex and tend to date within the same circles. Every single main character on the show experiences some form of heartbreak and some form of true love. With this much love and heartbreak floating around, it may be hard to keep track of all the details.

The following quiz will test your knowledge on the relationships that take place on the Office, whether they are serious or silly, brief or long lasting, you will be quizzed on what you know of your favourite character's love lives. Good luck!

Question 1

How Many Times Has Pam Beesly Been Engaged?

Pam Beesly is the Dunder Mifflin Scranton branch's secretary. She is soft spoken and kind hearted, yet loves making jokes with Jim to relieve office boredom. While Jim and Pam's friendship eventually blossoms into something more, before this happens, both lead their own lives and date different people. In fact, Pam has experienced serious love before committing to, and marrying Jim. Can you remember how many times Pam has been engaged in her life?

Question 2

Who is Pam's First Fiancée?

As previously mentioned, Pam experienced some serious love before marrying Jim. Her first fiancée was her college sweetheart whom she had been dating for many years. She was also engaged to him for quite a while, a fact that totally upset her and made her question if she would ever get married. Luckily, for all the viewers they did take so long to actually tie the knot because it allowed her to meet her one true love. Who was Pam's first fiancé?

Question 3

Who is Michael Scott's First On-Screen Girlfriend?

Michael Scott is not shy about proclaiming his need to love and to be loved. He hates to be alone and longs to find his life partner with whom he can start a family. When Michael first begins dating this lady, they must keep it a secret. She asks him to keep it a secret, but of course, typical Michael, he spills the beans. Although, eventually everyone knows and their tumultuous, disaster of a relationship becomes regular drama in the office and amongst his employees.

Question 4

How Did Michael And Jan Meet?

Michael and Jan's relationship is at first incredibly risky and could affect both of their careers. In fact, they specifically choose to keep the relationship under wraps in order to avoid unwanted attention or rumours from the Dunder Mifflin Scranton Branch employees and others employed by the company. There's of course, a reason why they should keep it to themselves and not let the word get out. We know now that they dated, and it became public, but how exactly did Michael and Jan first meet?

Question 5

What is the Name of Kevin's Fiancée?

Kevin Malone first applied to a warehouse position at the Dunder Mifflin Scranton branch; Michael instead gave him a job as an accountant and he has been working at the branch ever since, and let's just say in the end it really shows why he should've been in the warehouse instead. Although many of the employees regard him as silly, question his competence and rarely ever take him seriously, one specific lady loves him and decides she wants to spend the rest of her life with him. Who is Kevin's fiancée?

Question 6

Does Kevin Marry His Fiancée?

Kevin Malone is portrayed as the goofy, often dimwitted employee at the Dunder Mifflin Scranton branch. The accidental Accountant has a few other secrets, one of them is who the lucky lady in his life is. He begins the show with a fiancée who has committed to spending her life with him. She also has a daughter, giving Kevin a step-daughter. Can you remember if Kevin Malone ends up marrying his fiancée? Or does he go on to date others and perhaps even marry other people?

Question 7

How Do Michael and Jan Begin Dating?

Michael and Jan's love story is a central storyline for the Office's earlier seasons. What begins as a supervisor constantly annoyed with her employee, becomes a tumultuous and a hilarious unfortunate pairing. Michael and Jan initially keep their relationship under wraps after this event, and by initially, we mean Michael surprisingly didn't immediately blurt it out, he waited a whole few hours. During this specific episode, the two realize they could perhaps begin a relationship (a relationship which ultimately neither satisfies nor benefits either of them). How do Michael and Jan being dating?

Question 8

Why Do Michael and Jan Break Up?

As previously mentioned, Michael begins dating his former supervisor, Jan, after weeks of keeping it under wraps. What started out as a fun affair, that Jan kind of regretted most of the time, turned into a weird co dependency. The relationship is volatile and the two clearly are not a good fit for one another. But something specific happens that causes the pair to break up, unfortunately on bad terms. Can you remember what exactly happens in this hilarious, yet unfortunate episode?

Question 9

How Long Was Pam Engaged To Roy?

This question is a little harder than the other ones. Pam Beesly dated Roy Anderson, a worker in the Dunder Mifflin Scranton warehouse for a long time, before eventually, they finally got engaged. Although they remained engaged for awhile, the pair called it quits before they had the chance to actually go through with it. Michael Scott often enjoyed making jokes about Pam and Roy's engagement while the two were together. But do you remember how long they were engaged for?

Question 10

How Does Pam Decide to Leave Roy for Good?

Although Pam and Roy have been together for awhile and may have enjoyed wonderful moments before the shows premier, as soon as the series begins viewers notice that they now have a strained relationship. Pam clearly has chemistry with Jim who pays attention to her needs and emotions. And it makes the audience much more invested in their relationship than in the one she's in. Pam and Roy break up and get back together, but what causes Pam to leave Roy for good?

Question 11

What is the Name of Jim's First On-Screen Girlfriend?

Since the pilot episode of the Officer, viewers can clearly see that the goofy paper salesman Jim Halpert has feelings for Pam Beesly, the artsy branch's receptionist. Unfortunately, Pam is engaged to Roy Anderson and only sees Jim as a friend - or at least makes it seem that way. Nevertheless, Jim must move on and date other people. He dates a few different people actually, and even has a few serious relationships. What is the name of his first girlfriend on the show?

Question 12

How Does Jim Meet His First On-Screen Girlfriend?

Much to Jim Halpert's chagrin, his office best friend and fellow prankster and ally Pam Beesly is engaged to Roy Anderson. Jim must either wallow, or move on. Thankfully he decides to move on. They still remain very close, still play pranks together, and the audience at home still roots for them every step of the way, but alas, Pam is with Roy and Jim well, he's with a few other eligible bachelorettes. How does he meet his first girlfriend of the series?

Question 13

Who is the First Person to Whom Jim Reveals his Feelings for Pam?

Jim silently suffers as Pam remains engaged to Roy during season one and two. Hiding his true feelings has become progressively harder as their friendship continues to blossom and reinforces just how perfect they would be together. Yet, he still hides it. But he soon reaches his threshold and can no longer keep his secrets a feeling. During an office boat party organized by Michael, Jim confides in this particular person, revealing to them his love for Pam. Unfortunately, this person is notoriously bad for keeping secrets. Who does Jim tell?

Question 14

Who does Dwight Secretly Date?

Dwight Schrute is the office tattletale who takes pride in being the assistant to the regional manager (the "to" is very important). He also works alongside Jim as a paper salesman. Although Dwight may seem like he is too busy and serious to date while having a job, he is secretly seeing another person who works in the office, often meeting up around the office when they have moments to spare. Who does Dwight secretly date?

Question 15

How Does Jim and Pam's Secret Relationship get Revealed to their Colleagues?

Keeping office relationships a secret seems to be a running theme in this series. Perhaps because work relationships are complicated and in some ways involve everyone in the office- or maybe people just value their privacy. Jim and Pam continue the trend of secret work romances by not immediately telling everyone in the office that they have been dating for a few months... but of course, word gets out eventually. Do you remember how?

Question 16

How Does Jim Meet Karen?

Before Jim and Pam start dating, much to viewers enjoyment, they are both involved with other people. Timing really is everything for relationships and when Jim begins dating Karen Filipelli, Pam had broken off her engagement with Roy and had to face the sad reality that Jim was not single anymore or waiting for her. Jim and Karen date for awhile, and often have to interact with poor Pam at the same place of work. How do they originally meet?

Question 17

Why Does Jim Break Up with Karen?

Karen Filipelli is definitely a "cool girl." She can keep up with Jim's pranks and even has a few good pranks of her own up her sleeve, we almost start to forget how great Jim and Pam would be together, almost. She and Jim seem to really get along - they even discuss moving from Scranton to New York City together. However, this relationship does not last. Jim breaks up with her shortly after having this discussion. Can you remember why Jim breaks up with Karen?

Question 18

How Does Michael Scott Meet Carol?

Michael Scott loves love, in fact, one would even say he is quite obsessed with the idea of being in love, and more importantly, in someone loving him. One of his more serious relationships involve Carol Stills (played by lead actor Steve Carell's real life wife, Nancy Carell!). Michael has met different women in a myriad of ways, like through work, at restaurants and even at a wedding. But this relationship started off a bit differently. How did Michael meet business lady, Carol? Can you remember how exactly they meet?

Question 19

Why Does Carol Break Up with Michael?

Carol and Michael decide that they can date, but maybe not too seriously, especially in the beginning while they are just getting to know each other. Based on the way they met, Carol seems a bit apprehensive to get too seriously involved with Michael. She very early on realizes just how clingy and needy he can be and how he desperately wants to be in a serious relationship. She tries to look past it and keep it casually. What does Michael ultimately do that makes her break up with him?

Question 20

Who is the Love of Michael's Life?

Michael's string of relationships include the infamous Jan and the mild tempered Carol Stills, amongst others. But there is one particular lady he just cannot seem to get his mind off of. Is it someone with whom he had bad blood and he is filled with guilt and regret, or someone who sticks around forever after they meet. People come and go, but this particular lady seems to stick around- even if she is not physically there.

Question 21

How Does Jim Propose to Pam?

Since Jim and Pam broke the news of their relationship, the Office viewers have been anxiously awaiting their wedding. Everyone knows it will happen, only no one knows precisely when- including Pam. Jim and Pam discuss marriage, but Jim makes a game out of it (in typical Jim fashion), pretending like he may propose during inappropriate times and scaring Pam. Aside from all the fun and games, when Jim proposes it truly is a moment to remember, both for the couple and the show's viewers.

Question 22

How Does Andy Ask Angela Out?

Andy, an employee who transfers from the Stamford branch along with Karen and Jim, decides he wants to date someone in the office. After trying his luck with Pam, he sets his sights on Angela. Now, Angela is a tough lady, and an even tougher nut to crack. There is not a lot that makes her laugh or gets her seal of approval. Yet, somehow, Andy in a way wins her over. What does Andy do that convinces Angela to date him?

Question 23

Who is Oscar's Serious Boyfriend?

Before Michael Scott unfairly and meanly (but unknowingly) revealed Oscar's sexual orientation to the office, no one knew much about his dating life. After learning he is gay, employees at the Dunder Mifflin Scranton branch, as well as viewers of the Office, learn more about Oscar's love life. Dunder Mifflin pays for Oscar to take two months off and go on vacation with his serious boyfriend, in order to avoid a lawsuit. Who is his boyfriend?

Question 24

Which Farm Girl does Dwight Begin a Relationship with Later on in the Show?

This is a very tough question that only viewers who have watched the Office from start to finish (or at least the later episodes) may be able to answer. While Angela is dating other people, Dwight is too. He begins to see a lady from the same farming community as him, whom he is able to relate to on matters that no one else in the office would understand. However, the relationship does not last. Do you remember her name?

Question 25

Who Does Holly Date After She is Transferred to Nashua?

After Holly Flax replaces Toby as HR representative at the Scranton branch, she and Michael grow immensely fond of each other and begin a short relationship. Unfortunately, corporate decides to transfer her again to Nashua, and Holly decides not to continue the relationship, after enduring a tearful and long carride with Michael to her new home. During Holly's time at the Nashua branch, she meets someone new and begins dating them over it- it eventually becomes quite serious. Can you remember Holly's new boyfriend's name?

Question 26

Who is Phyllis Married to?

Phyllis, whose maiden name is Lapin, is a salesman who works alongside Dwight, Jim and Stanley. She was also Michael's high school classmate. She keeps her relationship with this particular person under wraps, more so because no on asked rather than because she was trying to keep it a secret. When she reveals she is marrying this person, who also works in the same building, her colleagues are extremely happy for her- and a tad bit surprised. Who is Phyllis married to?

Question 27

Why Do Andy and Angela Break Up?

Andy and Angela begin dating after Andy performs a song for Angela with his a cappella teammates on speaker phone and later gives her a cat. The unlikely duo continue dating and eventually get engaged. As Andy is busy planning the wedding while simultaneously trying to please Angela with all her picky requests, Angela is off doing her own thing. The pair eventually experience a bad break up that somewhat haunts the office. Why do they call their wedding off?

Question 28

Whose Friend Develops a Crush on Dwight After They Meet at a Wedding?

In season 6 of the Office, viewers get to watch the long awaited wedding of Jim and Pam. The couple decides to hold their wedding and reception at a hotel in Niagara Falls, a few hours away, so that fewer people from the office show up- but luckily for viewers, Michael gives everyone a day off work to make the journey. At the wedding, Dwight begins talking to this person's friend, who eventually develops quite a crush on him, even though is he generally uninterested.

Question 29

Who is Kelly Kapoor's On and Off Boyfriend?

Kelly Kapoor works in customer service at the Dunder Mifflin Scranton branch. She is generally quite friendly and loves to gossip, which is why she is the go-to-girl on who is dating who in the office. She finds herself in an on and off relationship with this Dunder Mifflin employee who frankly, does not treat her that well. Fun fact, this office relationship is supposed to be an exaggerated joke about this couple's (which includes Mindy Kaling and someone else) real life relationship. Who is Kelly Kapoor's boyfriend?

Question 30

How Many Men Have Duelled Over Angela's Love?

Angela's tough exterior, pickiness and general lack of agreeability may make her an unlikely reason to have a duel. Yet, in the series, viewers witness a duel between Andy and Dwight for Angela's affection, resulting in both of them deciding to end things with her. Angela, during a valentine's day support circle for single people (hosted by Michael, of course) reveals that that was not the only duel to involve her. How many men have duelled over Angela's love?

Question 31

Which Two Couples Go On an Uncomfortable Valentine's Day Lunch Together?

On the same day that Angela reveals her past romances and duels men have had over her to the group of single office employees at their support group, the employees in relationships decide to enjoy Valentines Day. Two couples go on a Valentines day lunch with one another. What starts off as a cute way to celebrate relationships and friendships, soon becomes incredibly awkward and uncomfortable. Which two couples get awkward together?

Question 32

What is the Name of Stanley's Second Wife?

Stanley Hudson, or Stanley the manly as Michael Scott likes to call him, does not reveal much about his life outside of the office. Although, viewers are given glimpse into his home life, often without him even wanting to reveal that information. During the first season, Stanley takes his second wife to the Dundie Awards at Chili's, hosted by Michael Scott. He also speaks about his wife at certain times. What is the name of Stanley's second wife?

Question 33

Who Does Angela Have a Child with?

In season 8 of the Office, Angela Martin marries this person and has a child with him. The couple name their son, Philippe, after her cat. This upsets Pam Beesly who is also pregnant and naming her son Philippe, but after her grandfather, which to be honest, holds a bit more water than a cat, considering one of the cats Dwight got her was named Garbage. Be careful with this question, Angela does have a child while married to this person, but is Philippe truly his son? Can you remember?

Question 34

Who Does Kelly Begin Dating to Make Ryan Jealous?

When this person stands up for Kelly in the show's 4th season, they quickly begin a confusing relationship. This character's at times stoic demeanour is in stark contrast to Kelly's constant excitement. It becomes evident that she is also dating him to make her ex Ryan Howard jealous, because when Ryan comes to Dunder Mifflin to visit after being promoted, Kelly turns up the PDA with her new boyfriend. Can you remember who Kelly begins dating to make Ryan jealous?

Question 35

Is Toby Flenderson Married?

It's easy to feel bad for the Dunder Mifflin Scranton branch's Human Resources representative, Toby Flenderson. He is often the butt of many jokes, and the cause of Michael Scott's anger, even if it has absolutely nothing to do with Toby. When Michael is feeling especially mean, he sometimes refers to Toby's life outside the office. Does Toby Flenderson have a wife and does Michael make jokes about her to upset him? Or does Michael make jokes about him being forever alone?

Question 36

Who Does Stanley Cheat on His Wife with?

Viewers of the Office meet Stanley's second wife, Teri, when he brings her to the Dundies Awards at Chili's. In the show's later seasons, a summer intern at the Dunder Mifflin Scranton branch mentions seeing Stanley at a bar with a lady, even though Teri is meant to be out of town. The intern's information risks becoming known to the entire office due to Michael Scott's inability to keep a secret. What is the name of the lady with whom Stanley is having an affair?

Question 37

Why Do Dwight and Angela Break Up the First Time?

Dwight Schrute and Angela Martin's on and off relationship may confuse many viewers- they certainly see something very special in one another. Although the pair eventually gets married, they break up and get back together a few times, often while also dating other people. The couple's first break up, which Angela instigates, devastates Dwight, especially since Angela later gets engaged to Andy Bernard. Why did Angela decide to break up with Dwight?

Question 38

Which Two Employees Sign a Contract to Conceive a Child Together?

Nowadays, different ways to conceive a child are becoming more scientifically advanced. Culture and traditions behind conceiving a child are also become less rigid, and more flexible. This couple at the Dunder Mifflin Scranton branch decides to conceive a child, despite not being together and leading single lives. For added protection, the pair hilariously creates a contract covering minute details. All though neither employee follows through with the contract, they do end up having children.

Question 39

Whose Mother Does Michael Begin Dating?

Michael Scott is especially impatient to find the love of his life. His eagerness often gets him into situations that may upset others, as he is not always sensitive about who he dates or how he ends relationships. Michael meets this particular lady at a significant event and dives head first into a relationship, ultimately upsetting one of his employees. He eventually ends the relationship, causing even more anger in this particular employee.

Question 40

Where Do Jim and Pam Get Married?

Jim and Pam's wedding is an event that both viewers of the show, and their colleagues at Dunder Mifflin have been waiting for. Although almost anyone could have guessed Jim and Pam eventually get married, it may be harder to know when and where they choose to get married. Although Jim and Pam are amicable to their coworkers and consider them friends, the Scranton branch can at times get hectic. For this reason, the couple chooses to host their wedding out of town, even though the entire office still shows up.

Question 41

Where Do Dwight and Angela Get Married?

While Jim and Pam's wedding may be more expected to viewers and their coworkers, Dwight and Angela's may be more surprising. The constant break-ups, heartbreaks and scandals between these two quirky characters have definitely had all of us at one point believe they really are not good for each other. Alas, the show's finale depicts Angela and Dwight's wedding, both of whom are now more mature and more confident in their love for one another. Where does the pair get married?

Question 42

Where Do Jim and Pam Go on Their Honeymoon?

After getting married, Jim and Pam can look forward to spending some time alone and away from the office on their honeymoon. Their wedding destination is not tropical or far away, but is their honeymoon destination different? Do you think Jim and Pam truly have it in them to pack their bags and relax in a foreign city, or do you think they would prefer to stay close to home? Or, do you think they choose to stay in the United States but travel to an area that is very different from Scranton?

Question 43

Why Does Erin Break Up with Andy?

Erin Hannon replaces Pam as the Dunder Mifflin Scranton branch's receptionist when Pam leaves to join the Michael Scott Paper Company and later returns to Dunder Mifflin as a salesperson. Erin catches the eye of a few employees in the office. Eventually, after a long period of not being on the same page, Erin and Andy Bernard begin a relationship. The relationship, however, does not last. Erin leaves Andy and begins seeing another Dunder Mifflin employee. Why does this happen?

Question 44

Which Lady Already Has a Husband When Michael Begins Dating Her?

As previously mentioned, Michael Scott's eagerness to find the love of his life at times gets him into situations that hurt those around him. Dating Pam's mom was not the only time Michael has hurt or disappointed someone; Michael also dates a married woman. Although he initially does not know that she is married, when he finds out, he is not willing to stop seeing her, again putting his desire to be in a relationship, ahead of the relationship itself. Tsk tsk, Michael.

Question 45

What Profession Was Nellie's Ex In?

Nellie Betram sneaks her way into a job as manager at Dunder Mifflin. The original manager, Andy Bernard, is furious that Nellie takes over his job while he is away and influences the whole office to somewhat dislike her. When Jim and Dwight attempt to prank Nellie, they soon discover she has a painful past with an ex who broke her heart. The profession of her ex is an important reason that Jim cancels his prank.

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