The Office: 15 Pick-Up Lines Used By The Characters

There were plenty of relationships and flirtations throughout nine seasons of The Office. While fans obsess over Jim and Pam’s romantic timeline, there were other characters who dropped some serious pick-up lines on crushes. Of course, whether these pick-up lines actually worked or not is up for debate.

Some of The Office’s pick-up lines worked in their favor while others came after a few embarrassing attempts that weren’t working out too well. From Andy’s desire to escape loneliness to Michael Scott transforming into the one and only Date Mike, there were a handful of pick-up lines made by The Office characters made to impress someone special.

Updated on March 2nd, 2022, by Lynn Gibbs: The Office may have revolved around a paper company but romantic and platonic relationships were at the forefront of the series. Pick-up lines from The Office have been used for memes and jokes since they’re so wildly funny and a touch inappropriate — especially Michael Scott’s pick-up lines. Regardless of whether these characters are at work or in the parking lot, they love using a good pick-up line to make an impression. 

Dwight Schrute

“Are You More Of A Fruit Man Or A Root Man?” 

When Dunder Mifflin gets two new employees, Clark and Pete, Dwight took a liking to Clark immediately. Not only did Clark look like a miniature version of him but he was a fellow salesman who wanted to do well at work. He later became one of the more annoying characters but he and Dwight shared a unique bond.

When Dwight was trying to get to know Clark, he leaned in real close and asked if he was a “fruit man or a root man.” Clark assumed Dwight was hitting on him with a pick-up line like that and told him he wasn’t gay. Dwight’s false pick-up line was literal and he wanted to know if Clarke preferred beets over fruits, which made the scene funnier.

A Milk Maiden

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

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 told him he would be the perfect person to buy an auger with. While Clark was flattered by the compliment, he realized the woman was just using him because a guy like him has no idea what an auger even is. Dwight and Ester were far more compatible than Clark and one of Ester’s sisters.

Dwight Schrute

“Hello. This Is Dwight Schrute. If You Are Listening To This You Are A Lucky Woman Michael Has Seduced. Ah, To Be In Your Shoes…”

One of the best Michael and Dwight episodes is when the two are traveling to Niagra 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.

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–.”

Meredith Palmer

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

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 him.

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.

Dwight Schrute

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

Before Dwight and Angela broke up, had a child contract, and started an affair — they were secret lovers in a hidden relationship.

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.

Darryl Philbin

“So, You Still Missing Ryan?”

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 saw Darryl in a new light.

Once he was alone with Kelly, he slyly asked her if she was still missing Ryan. But after that performance, the only person she could think about was Darryl. And while it didn’t last long, the two started dating for a short time.

Michael Scott

*Ties (And Gags) A Cherry Stem With His Tongue*

In ‘Happy Hour,’ Jim and Pam were at a point in their lives where they were comfortable enough setting Michael up on a date. The trick was setting him up in a way where he didn’t realize it was a date. With the entire office at a local bar for happy hour, Pam invited one of her friends for Michael. The two hit it off and were enjoying themselves until Michael found out he was set up.

His entire attitude and behavior changed once he found out he was being set up. He then turned into, what he called, Date Mike. To impress the girl 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 and it was a scene that was hard to watch.

Michael Scott

“Are You Real Or Are You A Holly-Gram?”

In ‘Goodbye, Toby,’ Michael was thrilled to get rid of Toby from the office but was 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.

And then Holly walked in. Michael wanted to dislike Holly but he couldn’t. 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 an underrated duo who spoke a language only they understood.

Kevin Malone

“I Get Very Nervous Talking To Pretty Girls”

Kevin was proof that a person didn’t need to come up with a clever one-liner or show off a cherry-stem-tying-experience. He was honest and it paid off.

In ‘Bloodrive,’ Michael put together a Valentine’s Day party for singles in the Dunder Mifflin complex. Kevin met a woman named Lynn that 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 his favor and the two were seen together shortly after.

Andy Bernard

County Music, A Road Trip, And Frisbee Golf

When the Stamford branch merged with the Scranton branch, Andy was on a mission 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 that would 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. In this instance, Andy’s pick-up lines failed.

Andy Bernard

“You Looking For A Dinner And A Movie? You’re Not Going To Find It In That Box”

Andy didn’t just hit on Pam and Erin, as he also hit on Angela. Normally, Andy’s 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.

Gabe Lewis

“Mondays Suck”

Gabe didn’t have much luck in the love department. 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. She dated him for months even though she wasn’t attracted to him.

When his relationship with Erin didn’t work, he tried making things happen with Val from the warehouse. With 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.

Karen Filippelli

“Nice Basket”

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. In one episode, Jim decided to switch up his morning routine and bike to work instead of driving.

Seeing Jim walk to his desk drenched in sweat was too funny not to say something. While looking at Jim and his bike, Karen said “nice basket,” which received a flirty smile from Jim. It was small moments like this that made fans want Karen and Jim to end up together.

Andy Bernard

Andy Gave The Literal 12 Days Of Christmas

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 gifted Erin the 12 Days of Christmas. 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.

Michael Scott

“You Complete Me”

A guy like Michael doesn’t give up easily when it comes to women. He spent years using pick-up line after pick-up line on Jan until it finally worked. As soon as Jan admitted that there was a connection between them, Michael pulled out one more pick-up line 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 absolutely dramatic they were.

About The Author

Lynn Gibbs
(1644 Articles Published)

Lynn is a nomad who travels the globe on the hunt for her next adventure with her husband. A lover of being outside (and finding the best latte in town), Lynn is typically hiking, walking, or jogging when she’s not focusing on her love of writing. When it comes to shows streaming on Netflix or anything Bravo-related, Lynn’s your gal.

More From Lynn Gibbs