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.
As previously mentioned, not all of these relationships ended happily (particularly Michael and Jan’s horrible relationship), but viewers did get some incredible The Office pick-up lines out each and every one of them. The best pick-up lines from The Office 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. Here are the best The Office pick-up lines, who says them, and what episode they are from.
15 “Are You More Of A Fruit Man Or A Root Man?”
Dwight Schrute — Season 9, Episode 1, “New Guys”
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 The Office characters but he and Dwight shared a unique bond.
When Dwight was trying to get to know Clark, he leaned in real close, delivering one of the funniest The Office pick-up lines, 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.
14 “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 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 more compatible than Clark and one of Ester’s sisters.
13 “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.”
12 “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 him 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.
11 “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.
10 “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 saw Darryl in a new light, giving warehouse worker Darryl Philbin one of his few The Office pick-up lines. 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 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.
9 “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 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, resulting in one of the most memorable The Office pick-up lines. 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, resulting in a lot of gagging and choking.
8 “Are You Real Or Are You A Holly-Gram?”
Michael Scott — Season 4, Episode 14 “Goodbye Toby”
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. But then Holly walked in. Michael wanted to dislike Holly but he couldn’t, which lead to many an awkward Michael Scott quote and a few great The Office pick-up lines.
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 duo who spoke a language only they understood.
7 “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 The Office pick-up line 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.
6 “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 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, 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. In this instance, Andy’s The Office pick-up lines failed.
5 “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.
4 “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. 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. 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, and it remains one of the most awkward The Office pick-up lines.
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. 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, resulting 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. It was small moments like this that made fans want Karen and Jim to end up together.
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, but utterly hilarious for audiences.
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.
