7 Best ‘The Office’ Valentine’s Day Episodes, Ranked From Worst to Best

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While it’s always a good night to curl up on the couch with your friends at Dunder Mifflin, Valentine’s Day is really the perfect excuse to cozy up with a marathon of The Office. Sure, romance might not immediately come to mind when you think of the show, but The Office is actually packed with love story after love story (think: Jim and Pam, Dwight and Angela, Michael and Holly, need we say more?), making it a sweet post-dinner watch for you and your valentine.

No matter how dysfunctional, quirky, and awkward the coworkers at Dunder Mifflin may be, they always find a way to focus on what really matters: sharing your life with someone you truly love. While Pam and Jim’s relationship is a highlight, there are so many sweet moments between friends, coworkers, and lovers throughout the comedy’s nine seasons that make it perfect for Galentine’s or Valentine’s Day. Browse through this list of The Office “Valentine’s Day” episodes, ranked from worst to best, to figure out which you should stream. Here’s a hint: They’re all worth watching (or re-watching), especially since The Office will be leaving Netflix sometime this year.

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Season 9, Episode 16: “Couple’s Discount”

Nobody appreciates a bargain more than the coworkers at Dunder Mifflin, and this episode is proof. The office pairs into couples to take advantage of a local nail salon’s Valentine’s Day discount. In the midst of their fun, Andy returns from his three-month boat trip to find an empty office, along with his girlfriend (Erin) threatening to break up with him.



Season 3, Episode 24: “The Job”

While most of the episode covers typical workplace happenings, the quick interaction between Jim and Pam at the end of the episode is by far one of their most romantic. Just moments after Pam confesses that she thinks her and Jim won’t work out, he swings by her interview to ask her on a date — and as you know, the rest is history.



Season 9, Episode 21: “Livin’ the Dream”

Pam and Jim’s puppy love is over — and this episode shows Jim coming to terms with the fact that he needs to go “all in” with his family, leaving his Athlead job behind him. Meanwhile, Angela finally confesses her true feelings for Dwight, saying that she “loves him.”



Season 5, Episode 18: “Blood Drive”

Now that he’s broken up with Holly, Michael is having a hard time accepting his newfound single status, so he decides to host a single’s mixer at the office. But really, it’s just part of his master plan to reconnect with the woman who lost her glove at the company’s blood drive. Even though she doesn’t show, the rest of his colleagues console him and lift his spirits.



Season 6, Episodes 17 and 18: “The Delivery”

First comes Pam and Jim’s wedding, then comes their baby: In this two-part episode, which just so happens to be the most-viewed The Office episode of all time, we finally get a more-than-worth-it conclusion to the couple’s crazy love story. But this moment also inspires Michael to become the office’s (un)official matchmaker, so he organizes a date between Erin and Kevin … which she turns down because she’s actually interested in Andy.



Season 6, Episodes 4 and 5: “Niagara”

Get your first glimpse of Pam and Jim as a married couple (finally!) in this two-part episode. The whole crew travels to Niagara Falls for the wedding festivities, but things go south when Jim accidentally reveals that Pam is pregnant. Of course, things turn around in true The Office fashion — awkward antics, choreographed dances, and all.



Season 2 Episode 16: “Valentine’s Day”

Experience the ups and downs of Valentine’s Day at Dunder Mifflin with this holiday-themed episode. While Michael Scott is in New York City for business, the rest of the office is feeling the love: Angela gives Dwight a custom bobblehead doll, Phyllis is showered with gifts from her boyfriend, Ryan confesses his love to Kelly, and Jim casually wishes Pam a “Happy Valentine’s Day.”


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