- The Office had various relationships and breakups, with some iconic pick-up lines delivered throughout the show.
- Dwight Schrute had some unintentionally funny pick-up lines, showcasing his unique personality.
- The pick-up lines from the cast were often awkward, situationally funny, and reflective of their characters’ personalities.
Over the course of eight years and nine seasons, the workplace comedy The Office saw plenty of various relationships and breakups, often started by The Office pick-up lines. While the flagship romance of the series was that of Jim Halpert and Pam Beesly, the characters got together relatively early on in the show, with their relationship facing numerous ups and downs over the course of the series. However, this left room for the show to explore other office romances such as that of Dwight Schrute and Angela Martin, Michael Scott and Jan Levinson-Gould, and the forever-toxic Kelly Kapoor and Ryan Howard.
Not all of these relationships ended happily (particularly Michael and Jan’s horrible romance), but viewers did get some incredible The Office pick-up lines out of each of them. The best pick-up lines from The Office castare usually either awkward in their delivery or situationally funny. Surprisingly, some of Dwight Schrute’s funniest moments are his pick-up lines, whether inadvertent or entirely intentional, putting Date Mike to shame.
20 “I Think You’re Attractive And I Wanna Sleep With You.”
Ryan Howard – Season 6, Episode 25, “The Chump”
Ryan is known for his often misguided attempts at climbing the corporate ladder and his tumultuous relationship with Kelly Kapoor, along with coming off crass, which is why this line is Ryan to a tee. In an attempt to sleep with Pam behind Kelly’s back, Ryan drops this line on the receptionist, and it comes off confident but totally tactless, which also sums up Ryan’s time at corporate. What makes the line funnier is that the audacity and straightforwardness are unlike Ryan’s character, and he immediately regrets it. Ryan’s character arc in The Office is a cautionary tale of the modern ambitious young professional, and that includes their dating life.
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19 “Tonight Would Be A Convenient Night For Us To Have Some Intercourse”
Dwight Schrute – Season 7, Episode 8, “Viewing Party”
In “Viewing Party,” the staff of Dunder Mifflin gathers at Gabe’s apartment to watch Glee, and the quote comes from a private moment when Dwight is speaking to Angela. Dwight and Angela’s The Office romance was an ongoing thread throughout the series, marked by its strictly formal “contract” and often bizarre, pragmatic exchanges, which are meant to keep their relationship purely physical. Dwight’s line is the epitome of his character: direct, devoid of romanticism, and to the point. He approaches the subject of their romantic encounter with the same matter-of-factness he applies to his job as a paper salesman or beet farmer.
18 “Feels More Like A Third Date To Me”
Meredith – Season 7, Episode 5, “The Sting”
Known for her brash and unapologetic demeanor, Meredith says this one-liner to a salesman (Timothy Olyphant) when acting as a business owner so Michael can learn the skillful salesman’s tactic. Meredith botches the surprisingly well-put-together sting when she quickly falls for the salesman. When the salesman uses his charms on Meredith, she responds with the crossing-the-line pick-up line, hilariously hinting at the typical third-date expectations. With her no-nonsense attitude toward dating, this isn’t the only classic Meredith pick-up line in the episode, as she adds, “what is with this desk keeping us so far apart?“
17 “Are You More Of A Fruit Man Or A Root Man?”
Dwight Schrute — Season 9, Episode 1, “New Guys”
When Clark started at Dunder Mifflin, Dwight took a liking to him immediately. Not only did Clark look like a miniature version of Dwight, but he was a fellow salesman who wanted to do well at work. He later became one of the more annoying The Office characters but he and Dwight shared a unique bond. When Dwight was trying to get to know Clark, he leaned in close and asked if Clark was a “fruit man or a root man.” Clark assumed Dwight was hitting on him, but Dwight’s false pick-up line was literal, and he wanted to know if Clarke preferred beets over fruits.
16 “You Would Be A Great One To Buy An Auger With”
Ester’s Sister — Season 9, Episode 18 “Promos”
When Dwight became more serious with Ester, her family tried to do business with Dwight to split a tractor together. Ester, her sisters, and her dad showed up at Dunder Mifflin in the tractor, which Clark loved. Ester’s sisters began hitting on Clark and delivered one of the funniest The Office pick-up lines by telling him he would be the perfect person to buy an auger with. While Clark is flattered by the compliment, he realizes the woman is just using him because a guy like him has no idea what an auger even is. Dwight and Ester were more compatible than Clark and one of Ester’s sisters.
15 “If You Are Listening To This You Are A Lucky Woman Michael Has Seduced. Ah, To Be In Your Shoes…”
Dwight Schrute — Season 6, Episode 4 “Niagra: Part 1”
One of the best Michael and Dwight episodes is when the two are traveling to Niagara Falls for Jim and Pam’s wedding. While on the ride, the two talked about all of the potential women they could meet. Dwight even made a CD for Michael to play when he seduces a woman, resulting in one of the funniest The Office pick-up lines. As if pick-up lines weren’t enough for Michael, Dwight’s CD started out with him calling the woman “lucky” before finishing with,
“Ah, to be in your shoes. ‘What’s next?’, you’re probably wondering. Don’t be scared of your night in heaven.”
14 “Do You Like Being Alone With Me Right Now?”
Gabe Lewis – Season 7, Episode 23, “Dwight K. Schrute (Acting Manager)”
Gabe might not have said this line to Val or Erin, as he asks Andy the question, but the line cleverly reflects Gabe’s often clumsy and direct approach to personal relationships. Gabe, the lanky and somewhat eerie liaison between Dunder Mifflin and its corporate parent, Sabre, is not known for his social graces. It’s a mix of vulnerable and unsettling, mirroring Gabe’s character, who struggles to find the right balance between his corporate persona and his desire for genuine human connection. Andy’s response is even better, as he replies, “No, this is horrifying.”
13 “Hey Boom Guy, When Are You Gonna Boom Me?”
Meredith Palmer — Season 9, Episode 14 “Vandalism”
In season 9, Brian the boom operator for the documentary team began making appearances the closer he got to Pam. Brian got in trouble for interacting with Pam too much, so he tried keeping his distance. However, that didn’t stop Meredith from making a move on Brian and handing out one of the most iconic The Office pick-up lines. In one of Meredith’s more inappropriate The Office moments, she asked Brian when he was going to “boom” her. Meredith’s pick-up line failed and Brian turned her down politely before going back to work.
12 “Do You Like Candy? Because You’re Sweeter Than Candy.”
Dwight Schrute — Season 2, Episode 12 “The Injury”
Before Dwight and Angela broke up, had a child contract, and started an affair — they were secret lovers in a hidden relationship, resulting in plenty of hysterical The Office pick-up lines. When Dwight had his concussion, his true feelings for Angela came out when she was getting a candy bar from the vending machine. He was far more emotional and nicer than normal. With a candy bar in her hands, Dwight tried the pick-up line, “Do you like candy? Because you’re sweeter than candy.” Luckily for him, the line worked on Angela.
11 “So, You Still Missing Ryan?”
Darryl Philbin — Season 4, Episode 6 “Launch Party”
When Ryan left Scranton for a new life at corporate, Kelly was single yet again. But after Darryl rescues Kelly from one of Dwight’s threats, she sees Darryl in a new light, giving warehouse worker Darryl Philbin one of his few The Office pick-up lines. Once Darryl was alone with Kelly, he slyly asked her if she was still missing Ryan. But after that performance, the only person Kelly could think about was Darryl. And while they had one of the shortest relationships on The Office, the two did date, mainly so that Kelly could rub the relationship in Ryan’s face whenever he came around.
10 “Hi, I’m Date Mike, Nice To Meet Me. How Do You Like Your Eggs In The Morning?”
Michael Scott — Season 6, Episode 21 “Happy Hour”
In “Happy Hour,” Jim and Pam set Michael up on a date that he doesn’t realize it’s a date. Pam invites one of her friends to a local bar for Michael. The two hit it off and were enjoying themselves until Michael found out he was set up. Michael’s entire attitude and behavior changed after he figured it out, and he then turned into Date Mike. To impress the woman as Date Mike, he tried winning her over by tying a cherry stem with his tongue. Tying the cherry stem as a pick-up flirtation did not go well, resulting in a hard-to-watch lot of gagging and choking.
9 “Are You Real Or Are You A Holly-Gram?”
Michael Scott — Season 4, Episode 14 “Goodbye Toby”
In “Goodbye, Toby,” Michael is thrilled to get rid of Toby from the office but is bothered by the thought of someone new coming in. He realized it didn’t matter who took the HR position, as he loathed anyone in HR to begin with. Then Holly walked in. They had the same sense of humor and she understood him like others never had. As a way to lighten the mood and make an impression on her, Michael asked Holly if she was a “Holly-gram.” From there, the pair became a lovable The Office duo who spoke a language only they understood.
8 “I Get Very Nervous Talking To Pretty Girls”
Kevin Malone — Season 5, Episode 16 “Blood Drive”
Kevin was proof that a person didn’t need to come up with a clever pick-up line or show off a cherry-stem-tying experience. He was honest and it paid off. Michael put together a Valentine’s Day party for singles in the Dunder Mifflin complex. Kevin met a woman named Lynn who seemed equally as interested in him as he was in her. Sadly, he was so nervous talking to her that he panicked. After stepping away, he came back and apologized, saying he gets “nervous talking to pretty girls.” He even showed her how sweaty his palms were. This admission worked in Kevin’s favor and the two were seen together shortly after.
7 “I Started The Main Frisbee Golf Club At Cornell, Where I Went To College. I Live To Frolf.”
Andy Bernard — Season 3, Episode 9 “The Convict”
When the Stamford branch merged with the Scranton branch, Andy set out to make an impression. After making Michael his best friend, he moved on to love interests. With Jim’s “help,” Andy worked his magic on Pam. Unbeknownst to Andy, Jim fed him bad information, resulting in some hysterical The Office pick-up lines, that would definitely not work with Pam. Instead of casually complimenting Pam and asking her on a date, Andy suggested going on a road trip and listening to country music — pick-up lines that would never work on Pam. Eventually, they would play frisbee golf and smoke some cigars, more things that Pam had no interest in doing.
6 “You Looking For A Dinner And A Movie? You’re Not Going To Find It In That Box”
Andy Bernard — Season 4, Episode 6 “Launch Party”
Andy didn’t just hit on Pam and Erin, as he also hit on Angela resulting in their engagement at one point. Normally, Andy’s The Office pick-up lines wouldn’t have had an effect on Angela but considering she was fresh out of a breakup, she needed a distraction. This started the plotline of who was better for Angela, Dwight or Andy? Instead of using the same technique that Andy used on Pam, he gave Angela a gift as his pick-up line: a cat. The gift worked on Angela, and she agreed to go on a date with him now that she had a new cat to add to her home.
5 “Mondays Suck”
Gabe Lewis — Season 8, Episode 6 “Doomsday”
Gabe didn’t have much luck in the love department, or any department at all, really. Erin noted that the only reason why she agreed to date Gabe was that he was her boss and she was scared to say no. Erin dated Gabe for months even though she wasn’t attracted to him. When his relationship with Erin didn’t work, Gabe tried making things happen with Val from the warehouse. At a loss for words, Gabe’s pick-up line for Val was “Mondays suck.” Val nodded her head in agreement, clearly unaware of what Gabe was intending. This wasn’t Gabe’s best romantic quote, but he gave it his best.
4 “Just So You Know, Me And You, I Don’t Think That’s Ridiculous. Dot, Dot, Dot, Dot, Dot.”
Season 8, Episode 16, “After Hours”
It isn’t just Gabe who has an interest in Val in The Office, as it’s revealed that Darryl has a crush on her too, only Darryl has way more success. During an office meeting, Darryl and Val’s secret texts are revealed to the whole office, and the Dunder Mifflin employees openly analyze Darryl’s use of ellipses. At the end of the episode, Darryl straight-up tells Val the truth, implying the open-ended possibility between them. It’s a classic Darryl move to keep things casual but hopeful, and the line perfectly captures Darryl’s nonchalant charm and smoothness.
3 “Nice Basket”
Karen Filippelli — Season 3, Episode 6 “Diwali”
While Jim and Pam were the ultimate The Office couple, Jim and Karen had their good times too. When Jim started his new job at the Stamford branch, he and Karen had an instant connection. They had an easy banter that was reminiscent of his with Pam. This was on full display when Jim decided to switch up his morning routine and bike to work instead of driving. Seeing Jim walk to his desk drenched in sweat resulted in one of Karen’s The Office pick-up lines. While looking at Jim and his bike, Karen said, “nice basket,” which received a flirty smile from Jim.
2 “Is It My Fault That The First Eight Days Is Basically Thirty Birds?”
Andy Bernard — Season 6, Episode 13 “Secret Santa”
Knowing that his pick-up line for Pam didn’t work and his relationship with Angela failed, Andy tried something new with Erin. With Christmas around the corner, Andy begged Dwight to make Erin his secret Santa and gifted Erin the 12 Days of Christmas, literally. From turtle doves to French hens to calling birds, Andy gifted them all. Unfortunately for him, all of the surprising birds (or “gifts“) proved to be too much for Erin. They began attacking her and her cat and she begged him to stop. The 12 Days of Christmas gifts ended up being one of the worst The Office pick-up lines for Erin’s sake.
1 “You Complete Me”
Michael Scott — Season 3, Episode 11 “A Benihana Christmas”
A guy like Michael doesn’t give up easily when it comes to women, often to his own detriment. He spent years using pick-up line after pick-up line on his boss Jan until it finally worked. As soon as Jan admitted that there was a connection between them, Michael pulled out one of the most iconic The Office pick-up lines that he hoped would stick: “You complete me.” Jan seemed both impressed and disturbed by Michael, which was all part of her fascination with him. Jan and Michael’s episodes were some of the best because of how dramatic and wrong for each other they were.
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