Summary

• Dwight's pick-up lines are both hilarious and cringeworthy, showcasing his direct and matter-of-fact personality.
• Michael Scott's over-the-top romantic gestures often backfire but add to the comedic dynamic of the show.
• The various relationships and breakups in The Office lead to some of the most memorable and unforgettable pick-up lines on the show.

Over the course of eight years and nine seasons, the workplace comedy The Office saw plenty of various relationships and breakups — and the many The Office pick-up lines that started them make for some of the funniest dialogue in the show. While the flagship coupling of The Office was that of Jim Halpert and Pam Beesly, several Dunder Mifflin employees became romantically entangled. The show also explored other romances, like Dwight and Angela, Michael and Jan, and the forever-toxic Kelly and Ryan.

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 cast are 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.

25 "I Think You're Attractive And I Wanna Sleep With You."

Ryan Howard To Pam Beesley - 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 incredibly blunt The Office pickup-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.

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. Pam's reaction is also, of course, incredibly hilarious. There are several points when characters other than Jim attempt to make a at Pam in The Office, and Jenna Fischer's awkward or irate reactions always manage to sell them — especially in this instance, since Pam has made it no secret that she isn't a fan of Ryan.

24 "Tonight Would Be A Convenient Night For Us To Have Some Intercourse"

Dwight Schrute To Angela Martin - 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.

While some of the chat-up lines in The Office are incredibly smooth in a traditional sense, Dwight's are smooth because of him being him (and the women he flirts with, such as Angela, finding this inexplicably irresistible). This Dwight The Office pick-up 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.

23 "On A Scale Of One To Ten, How Hot Is That Dude Over There?"

Andy Bernard On Behalf Of Oscar Martinez - Season 5, Episode 8, "Business Trip"

While Dwight may come across as awkward to most but incredibly smooth to the right woman, Andy Bernard simply comes across as awkward. He's incredibly bad at flirting, and not just when he's doing it on his own behalf, either. This is a rare pick-up line from The Office that is delivered on someone else's behalf as Andy plays wingman for Oscar.

Though Andy's character in later seasons of The Office was not very likable, this episode shows how good of a friend he can be as he does his best to help Oscar find romance while on a business trip in Canada. Unfortunately, as a wingman, Andy is as clueless and bold as when he's approaching sometone for himself, and brazenly asking these two strangers what they think of Oscar's looks before quickly being told to leave. While it was certainly a risky move, Andy's heart was in the right place.

22 "A Real Man Swallows His Vomit When A Lady Is Present."

Dwight Schrute To Nellie Bertram - Season 8, Episode 17, "After Hours"

Though Dwight likes to let his work and dedication to Dunder Mifflin speak for itself, he shows several times in the series that he is not above playing games of corporate intrigue in order to win. In one memorable case, that even means seduction. One of several jobs Dwight holds in The Office is the head of a Special Projects team, which gives him a chance to impress Nellie (Catherine Tate).

Todd Packer is also trying to impress Nellie by seducing her, which causes Dwight to play dirty.

While Dwight would usually try to show his value to her by always being present for whatever task she needed him (and even when she doesn't), he instead has to rely on his wit and charm to stand out above a specific colleague. Unfortunately, Todd Packer is also trying to impress Nellie by seducing her, which causes Dwight to play dirty. He slips something into Todd's drink that causes him to vomit in front of Nellie. Dwight then swoops in to deliver this hilarious pick-up line.

21 "Feels More Like A Third Date To Me"

Meredith Palmer To Danny Cordray - Season 7, Episode 5, "The Sting"

Meredith is one of the funniest ing characters in The Office, and a key reason for this is that she treats her male colleagues like any stereotypical womanizer would treat their female ones. Known for her brash and unapologetic demeanor, Meredith says this one-liner to salesman Danny Cordray (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 Danny.

When Danny uses his charms on Meredith, he quickly realizes that he got more than he bargained for. Meredith responds to Danny's flirtatious sales tactics with this unbelievably forward The Office 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?"

20 "Are You More Of A Fruit Man Or A Root Man?”

Dwight Schrute To Clark Green — Season 9, Episode 1, "New Guys"

When Clark Green (Clark Duke) 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. It's one of several lines that showcase how Dwight is perhaps the source of the funniest chat-up lines in all of The Office, as it would completely be in-character for him if he had intended this as a romantic advance.

19 "You Would Be A Great One To Buy An Auger With”

Esther's Sister To Clark Green — Season 9, Episode 18 "Promos"

While Dwight and Angela eventually ended up together, she was't the only romantic partner he had in The Office. When Dwight became more serious with Esther (Nora Kirkpatrick) in season 9, her family tried to do business with Dwight to split a tractor together. Esther, her sisters, and her dad showed up at Dunder Mifflin in the tractor, which Clark loved. Esther'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.

Clark realizes Esther's sister is just using him because she can tell he has no idea what an auger even is.

While he is flattered by the compliment, Clark realizes Esther's sister is just using him because she can tell he has no idea what an auger even is. Dwight and Esther were more compatible than Clark and one of Esther's sisters, but their relationship also inadvertantly led to one of the funniest pick-up lines in The Office that came from a guest character on the show.

18 "If You Are Listening To This You Are A Lucky Woman Michael Has Seduced. Ah, To Be In Your Shoes..."

Dwight Schrute To Michael Scott — 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."

It's one of several moments throughout The Office where Dwight's adoration for Michael can easily be misconstrued as latent affection. While Dwight doesn't have any romantic inclination toward Michael in reality, their dynamic still makes for some incredibly hilarious moments throughout the show. Dwight is willing to do literally anything for Michael, and it often makes Michael uncomfortable.

17 "Do You Like Being Alone With Me Right Now?"

Gabe Lewis To Andy Bernard - Season 7, Episode 23, "Dwight K. Schrute (Acting Manager)"

If there's one character in The Office who is even more awkward when it comes to matters of the heart than Andy Bernard, it is Gabe Lewis. Somehow though, Gabe still manages to find one or two girlfriends on the show, and each realtionship of his comes with a slew of incredibly awkward moments. 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 — as this hilariously awkward The Office pick-up line shows. 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."

16 “Hey Boom Guy, When Are You Gonna Boom Me?”

Meredith Palmer To Brian The Boom Operator — Season 9, Episode 14 "Vandalism"

It's unsurprising that Meredith is the source of many of the best and funniest pick-up lines in The Office, since she spends more time on the show propositioning people than any other character. However, one of the most hilarious was when her loneliness and need for physical affection led ot her breaking the fictional fourth-wall between the fake show being filmed in the mockumentary sitcom. In season 9, Brian, the boom operator for the documentary team, began making appearances the closer he got to Pam.

One of Meredith's more inappropriate moments

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 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.