Looking For The Best ‘The Office’ Pick Up Lines? We Got You On This!

Admit it: All of us have used some cheesy pickup lines to break the ice with our crushes at least once! After all, we desperately want to impress that certain someone and convince them that we are silver-tongued. Who can blame us for that? Unfortunately, the reality is much harder than it sounds, and all the characters from The Office know it all too well. 

When it comes to romance, Dwight Schrute (Rainn Wilson); Michael Scott (Steve Carell), and the rest of the crew have had plenty of embarrassing attempts, just like any of us. Still, there is one thing for sure: They know how to play with words. From Creed Bratton’s bold approach to Michael’s priceless one-liners, we’ve compiled a list of the greatest (and most hilarious) The Office pick-up lines. Perhaps you will learn a thing or two from them! 

FYI, the result might vary. 

The Office Pick-Up Lines – “So, You Still Missing Ryan?”

There’s no denying that Ryan and Kelly formed one of the most toxic relationships in the series. Even their loyal fans have to admit that. We usually see them in an on-again and off-again kind of situation, thus giving Darryl a chance to step in between. 

When Ryan returns to Dunder Mifflin Scranton, he and Kelly find themselves in an awkward situation. They were not together at the time, but there is enough tension to draw them back into one other’s arms whenever they interact. 

However, as Darryl saved Kelly from Dwight, the way Kelly looks at him has changed. Of course, Darryl wouldn’t miss this opportunity. As soon as they are alone, he slyly asked her if she was still missing Ryan. After Darryl’s heroic act, though, Kelly is probably thinking, “Ryan who?”.

Darryl, Ryan, And Kelly’s Love Triangle

Well, this might not be one of the best The Office pick-up lines, but it is very common and realistic. Have you ever asked your crush if they are still missing their ex? 

The Office Pick-Up Lines – “Nice Basket”

Jim and Karen share an instant connection. We know it the moment Jim arrives at the Stamford branch. Whenever they are together, there is a light banter that reminds us of his time with Pam.  ​

Something Is Going On Between Jim And Karen
There Is Definitely Something Between Jim And Karen – Source: Showbiz Cheat Sheet

In one episode, Jim decides to ride his bike to the office instead of driving. Seeing Jim walk to his desk soaking wet is too amusing to ignore, but Karen doesn’t laugh at him. She just glances at his bike and murmurs, “nice basket”. As a result of this little irony, Jim smiles flirtatiously at her. Bingo! 

Michael Tied A Cherry Stem (And Gagged) To Catch His Date’s Attention

Do you still remember the “Happy Hour” episode, when Jim and Pam tried to set Michael up on a date? Their plan was to trick Michael into believing that it is not a date because if he knows, he will mess it up. When all the officers gather at a local bar for happy hour, Pam called one of her pals over for Michael. The two got along well and were having a good time until Michael discovered that he had been set up. 

Immediately, Michael’s expression changed, and we know bad things are coming: Here comes the “Date Mike”! He tries to impress the girl by tying a cherry stem with his tongue, and of course, things turn out to be a disaster. Don’t do this unless you want to scare the hell out of your crush! 

Don’t Follow Any Of Michael’s Dating Advice
Date Mike Knows How To Ruin Any Date – Source: Screen Rant 

“I Get Very Nervous Talking To A Pretty Girl”

Are you tired of those cheesy Instagram DM pick up lines? If so, there is something you need to learn from Kevin! This man proved that you don’t have to come up with an impressive one-liner or brag about your cherry-stem-tying-skill like, ahem, a certain someone. His pick-up line is straightforward, just like his personality, and it turns out well for him. 

Kevin Malone’s Pickup Line
Regardless Of What He Seems, Kevin Knows How To Flirt – Source: Pedestrian TV 

In Bloodrive, Michael hosts Valentine’s Day party for loners in Dunder Mifflin. Glad to see that he finally does something nice for his friend, since it is at the party that Kevin bumps into an attractive lady named Lynn. The two are drawn to each other, but he becomes anxious and can’t bring himself to get the conversation going. 

Fortunately, after taking a little break, he returns and apologizes, explaining that he feels “nervous talking to a pretty girl”. He even let Lynn see how sweaty his palms are. Lynn (and all the audiences, I know it!) chuckles at this cuteness, and the two get together shortly after. Who says shy guys don’t know how to flirt?

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

In “Goodbye, Toby”, Michael is relieved to have Toby out of the office. He doesn’t get to bask in happiness for long, though, since a new face is coming in. That’s when our dear Michael figures out that it is not all about Toby, but he loathes anyone in HR, to begin with. 

But guess what? Holly arrives, and Michael can’t get his eyes off her! He tries his best to dislike Holly, but all of his efforts end up in vain. The two share a sense of humor, and for god’s sake, she is way cooler than Toby. 

Eventually, he gives up and delivers one of the most iconic The Office pick-up lines: “Are you real, or are you a Holly-gram?”. Thanks to this moment, season 4 is considered the best season of The Office. The fact that they engaged at the end of season 7 proves that using your crush’s name for a pick-up line always works! 

The Moment We Knew Michael And Holly Are Perfect For Each Other

Country Music, A Road Trip, And Frisbee Golf Make The Perfect Combo

As soon as Stamford and Scranton become one, Andy desperately wants to make an impact. After acknowledging Michael as his best buddy, Andy’s next mission is to find a love interest. Thanks to Jim, he finds his target: Our sweet girl Pam. Of course, Jim gives him lousy tips that would not work with Pam, and Andy is gullible enough to fall for it. 

Andy Falls For Jim’s Tricks - the office pick up lines
But, I Mean, Who Would Trust What Jim Says? – Source: TVLine

So, instead of casual pick up lines, Andy asks Pam on a date right away. He tries to take her on a road trip while playing country music. During the trip, they would play frisbee golf and have some cigars. This is not Pam’s cup of tea, but maybe your girl will enjoy a date like this! 

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

But Pam is not Andy’s only target. He also has a thing for other ladies and, most notably, Angela. Angela would ignore him in most cases, but she just went through a breakup at the time. That said, she needs anything to take her mind off the incident, and Andy comes at the right time. 

Andy does learn from his mistake, at least: He doesn’t try to ask Angela out on a date, just like how he does with Pam. Instead, he gets Angela a gift, saying “You looking for dinner and a movie? You are not gonna find it in that box”. Not the sweetest, I’d say, but the thing inside the box is: Andy gives Angela a kitten. 

Angela And Cats - the office pick up lines
And She Goes Crazy About It – Source: ComicBook

No one can resist a cat, not even a cold and stern woman like Angela. The gift ultimately works and Angela agrees to start dating him. Lesson learned: When in doubt, give your crush a kitten (as long as they are not allergic). 

Andy Gave Erin The 12 Days Of Christmas, Literally

As you can guess, Andy’s relationship with Angela doesn’t last long. How long does it take for him to get over this? A few episodes, I suppose. Soon enough, he moves to the next target, Erin. 

After two failed attempts, he wants to try something different. With Christmas around the corner, The ‘Nard-Dog comes up with a brilliant idea: He gives Erin the 12 Days Of Christmas. From turtle doves to French hens, everything that can be labeled “birds” is sent to Erin. 

Andy Gives Erin The 12 Days Of Christmas

Sadly for him, Erin is unable to handle all of the “gifts” he has brought her. She pleaded with him to stop it when the birds starts to attack her and her cat. 

The Office Pick Up Lines – “Mondays Suck”

Trust me when I say, “Monday sucks” makes one of the best morning pick up lines. Everyone hates Monday, so your crush can immediately relate to this. 

Just look at Gabe. Throughout the series, he is ridiculed for having the worst luck in love. Even Erin said that the only reason she dated Gabe was that she didn’t want to say no to her employer. The two were in a relationship for months even though Erin didn’t have any feelings toward Gabe. 

When he realizes things don’t go well with Erin, Gabe tried to hit it up with Val from the warehouse. After running out of things to say, he makes his final attempt to flirt: “Monday sucks”. Val couldn’t agree more, but whether she gets his intention or not is still not sure. Well…at least your certain someone will always agree with you on this. 

Gabe The Office - the office pick up lines
We Feel You Gabe! – Source: Imgflip

“Do You Like Being Alone With Me Right Now?” 

In the episode “Dwight Schrute Acting Manager”, a desperate Gabe asks Andy if he would like the two to be alone. When Andy tells him it’s horrifying, Gabe busts out in tears, saying he doesn’t want to be alone with himself either. 

“Do You Like Being Alone With Me Right Now?”

O…kay, I’m not telling you to embarrass yourself. This is not really a pick-up line, but taking it out of context, it *might* make a decent pickup line. Next time, try to ask your crush if he or she wants to be alone with you. With the right attitude, it won’t make you look like a desperate preying mantis! 

“Are You From Accounting? Because I Was Ac-counting On Asking You Out Later!” 

Another marvelous line you can learn from Kevin Malone. Since the encounter with Lynn, he seems to be much more experienced. This is the perfect line to drop around the office for that special someone you’ve got your eyes on, especially if he or she is an accountant. Accounting is boring, you say? 

“Just So You Know, Me And You, I Don’t Think That’s Ridiculous. Dot, Dot, Dot, Dot, Dot”

Remember what Darryl tells Val in the episode “After Hours”? Just so you know, if you want to make your certain someone feel extra special, you can add “exclamation mark, exclamation mark, winky face, winky face.” They’ll be so flattered!

“You Complete Me” 

You should save the last for the best – that’s why this is the last one in our list of The Office pick-up lines. It’s not between my favorite couple, but it is effective, versatile, and demonstrates Michael’s personality very well. 

Being a Sagittarius, when it comes to ladies, Michael isn’t one to give up quickly. He spent years trying pick-up line after pick-up line on Jan until he finally finds one that works. Right after Jan admits that there is something between them, Michael delivers the best one-liner he has ever had: “You complete me.” 

Michael Scott’s “You Complete Me”

Maybe Jan looks a bit disturbed, but at the same time, she is impressed as well. That’s all part of her fascination with Michael, so this line surely does its justice. 

Flirt At Your Own Risk! 

Now, with all of these The Office pick-up lines we compiled, you will have to see this iconic TV series in a new light. It’s not only a sitcom but also a complete guide on how to get your crush’s attention! Be careful, though, because you won’t know what kind of attention you will get with these lines. There is a chance they will get you fired (or at least slapped), so flirt at your own risk! 

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