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.

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.

The Dwight The Office pick-up line is the epitome of his character: direct, devoid of romanticism, and to the point.

The 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"

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 he is as a single man

Unfortunately, as a wingman, Andy is as clueless and bold as he is as a single man, 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 the work 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.

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. It is the kind of thing Dwight thinks would impress a woman but is more likely to revolt them.

21 "Feels More Like A Third Date To Me"

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

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.

With her no-nonsense attitude toward dating, this isn't the only classic Meredith pick-up line in the episode

When Danny uses his charms on Meredith, she responds 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.

Clark assumed Dwight was hitting on him, but Dwight's false pick-up line was literal

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.

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

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

When Dwight became more serious with Esther, 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.

He realizes the woman is just using him because a guy like him has no idea what an auger even is.

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.

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."

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

Gabe Lewis To Andy Bernard - 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 — as this hilariously awkward The Office pick-up line shows.

It's a mix of vulnerable and unsettling, mirroring Gabe's character

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"

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.

One of Meredith's more inappropriate moments

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.

15 "Do You Like Candy? Because You’re Sweeter Than Candy.”

Dwight Schrute To Angela Martin — 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. This hidden romance also resulted 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.

Luckily for him, the line worked on Angela.

Dwight was far more emotional and nicer than normal, which is always hilarious when it comes to Dwight, but when this translates to him attempting to flirt in a more traditional sense it becomes laugh-out-loud funny. 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.

14 "So, You Still Missing Ryan?"

Darryl Philbin To Kelly Kapoor — Season 4, Episode 6 "Launch Party"

When Ryan left Scranton for a new life at corporate, Kelly was single yet again. However, after Darryl rescues Kelly from one of Dwight's threats, she sees Darryl in a new light, giving warehouse worker Darryl the chance to woo Kelly with some smooth words. Once Darryl was alone with Kelly, he slyly asked her if she was still missing Ryan.

After this smooth The Office pickup-line, the only person Kelly could think about was Darryl.

However, after this smooth The Office pickup-line, the only person Kelly could think about was Darryl. 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.

13 "Well Actually, The Branch Is... Can You Be At My Place In 20 Minutes?"

Meredith Palmer To A Warehouse Worker - Season 3, Episode 7 "Branch Closing"

In the episode "Branch Closing," the Dunder Mifflin Scranton branch is in chaos with rumors of it closing. While most of the employees spend the day worrying about their future, Meredith decides to fulfill a deal she made with one of her coworkers that they would sleep together on the last day of work. Unfortunately, she cannot remember who she made the deal with.

Though she is about to let him know that the branch has been saved, she changes her mind and delivers this direct pick-up line.

After Scranton's branch is saved at the last minute, Meredith gets a call from one of the former warehouse workers who heard the branch was closing and reveals he is the one she made the deal with. Though she is about to let him know that the branch has been saved, she changes her mind and delivers this direct pick-up line.

12 "Hi, I'm Date Mike, Nice To Meet Me. How Do You Like Your Eggs In The Morning?"

Michael Scott As Date Mike — 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.

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.

11 "Are You Real Or Are You A Holly-Gram?"

Michael Scott To Holly Flax — Season 4, Episode 14 "Goodbye Toby"

In "Goodbye, Toby," one of the best episodes of The Office, 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, and he quickly realized she was the love of his life.

Holly and Michael had the same sense of humor, and she understood him like others never had.

Holly and Michael 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.

10 "The Two Levels Being, Welcome To Scranton... And I Love You"

Michael Scott To Holly Flax - Season 4, Episode 14 "Goodbye Toby"

Michael and Holly's relationship in The Office ends up being one of the most endearing on the show. However, despite Michael initially being apprehensive about another HR person, when he does decide that he likes her, he goes all in. Michael asks Jim for advice when making a playlist for Holly that is meant to convey two very important messages.

His declaration of love for her moments after meeting her for the first time is a classic case of Michael getting carried away.

While it is nice for Michael to offer a personalized welcome to Holly, his declaration of love for her moments after meeting her for the first time is a classic case of Michael getting carried away. He is a romantic at heart, but luckily Jim convinces him it is too early to tell her he loves her, which might have saved their future relationship.

9 "I Lost My Head When I Fell In Love With You."

Michael Scott To Holly Flax - Season 7, Episode 19 "Garage Sale"

After Holly and Michael broke up in The Office season 5, it seemed like that was the end of the fan-favorite couple. However, the pair continued to circle each other for years until they eventually reignited their romance, leading to Michael deciding to propose to her. This was one of the rare decisions by Michael that everyone was behind but some of his friends wanted to ensure he didn't go over the top with his proposal.

While the others convince him to abandon that idea, given Holly's similar sense of humor, it might have worked.

This proved to be a good instinct as one of Michael's ideas for proposing included throwing a dummy off a roof, so its head would pop off, allowing him to deliver this pick-up line. While the others convince him to abandon that idea, given Holly's similar sense of humor, it might have worked.

8 "I Get Very Nervous Talking To Pretty Girls"

Kevin Malone To Lynn — 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.

This admission worked in Kevin's favor and the two were seen together shortly after.

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 To Pam Beesley — 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 pick-up lines, that would definitely not work with Pam.

Andy suggested going on a road trip and listening to country music — pick-up lines that would never work on 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 To Angela Martin — 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 the love triangle between Angela, Dwight and Andy.

Instead of using the same technique that Andy used on Pam, he gave Angela a gift as his pick-up line: a cat.

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.