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The Office's Most Memorable Valentine's Day Episodes

These Valentine's moments all have a place in television history.

By McKenzie Jean-Philippe

The Office may be known for its laugh-out-loud moments, Michael Scott's (Steve Carrell) obnoxious antics, and plenty of "That's what she said" jokes, but it also has a soft side. 

How to Watch

Watch every episode of The Office on Peacock.

Romance was a constant throughout the comedy's eight years on air. Think Jim (John Krasinski) and Pam's (Jenna Fischer) epic friends-to-lovers storyline, and Dwight (Rainn Wilson) and Angela's (Angela Kinsey) quirky road to the altar. But Valentine's Day episodes were really the show's time to shine, no matter how odd they were. So if you're looking for a little The Office romance this year, we've listed the series' must-see Valentine's Day moments. And we've even mixed in some episodes that aren't centered around February 14, but are still a must-mention if you have the love bug.

Season 2, Episode 16 ("Valentine's Day")

The Dunder Mifflin employees were very busy during the series' inaugural Valentine's Day episode. It includes a major milestone for Michael and Jan's budding relationship when the two share a kiss after an awkward meeting at corporate. Back in Scranton, Angela gifts her secret boyfriend, Dwight, with his very own bobblehead—a beloved moment for many fans of the show. Meanwhile, Bob Vance (of Vance Refrigeration) gifts Phyllis various presents throughout the day; Ryan mistakenly hooked up with an excited Kelly the day before; and Pam is left unimpressed by Roy (and longing for Jim) when his only offer on the special day is "the best sex of her life".

Season 2, Episode 22 ("Casino Night")

While not an actual Valentine's Day episode, many will agree that "Casino Night" is one of the most romantic in the comedy's history. The minor moments? Dwight's PDA with Angela ends in a slap, and Michael is delighted to find himself in a love triangle when both Jan and Carol show up as his dates to the festivities. But what fans will remember most is this is the episode where Jim finally tells Pam he's in love with her. And though she breaks his heart and tells him that he's "misinterpreted" their friendship, by the end of the episode the pair share their very first kiss.

Season 5, Episode 18 ("Blood Drive")

This episode chronicles Michael's first Valentine's Day since breaking up with Holly, and he nearly rebounds with a fellow donor at their building's annual blood drive. He ends up throwing a singles' mixer in hopes of finding the mystery woman, but he comes up empty handed. 

Meanwhile, Jim and Pam go on a double date with Phyllis and Bob Vance—which was going well until the latter couple slipped off for an extended amount of time. When trying to figure out what happened to them, a disgusted Jim and Pam discover that Phyllis and Bob went to the restaurant's bathroom to have sex in one of the series' most scandalous and hilarious scenes.

Season 6, Episodes 4 & 5 ("Niagara" Part 1 & 2)

While "Niagara" Part 1 and 2 are also technically not about Valentine's Day, they're incredibly important episodes for Pam and Jim shippers everywhere. After six seasons of one of the most popular friends-to-lovers story arcs in television history, Pam and Jim got married in a destination wedding at Niagara Falls—and the whole office was invited. They even mimicked a viral video and danced down the aisle to Chris Brown's "Forever." And yes, we may have shed a tear.

Season 6, Episode 16 ("The Manager and the Salesman")

Season 6's actual Valentine's Day episode marks Jo Malone's (Kathy Bates) introduction to show as the CEO of Sabre. It also follows the early days of Andy and Erin's romance, when he sends a Valentine to every member of the office in efforts to disguise his crush. But in the process he mistakenly gives Kelly the wrong impression that he's interested in her.

Season 7, Episode 16 ("PDA")

Three couples got the spotlight, starting off with Michael and Holly's reignited romance. The two are so infatuated with each other that Gabe (Zach Lewis) has to hold a meeting advising against excessive amounts of PDA. Meanwhile a tipsy Jim and Pam spend the day attempting to have sex in the office after learning they're the only employees who haven't. Lastly, despite Andy and Erin's clear chemistry, he still helps her solve a Valentine's scavenger hunt organized by her boyfriend, Gabe. 

The Office Valentines Day

Season 8, Episode 14 ("Special Project")

The romance in this episode focuses on Darryl and his crush on fellow warehouse worker, Val. He buys her special cashmere gloves for Valentine's Day after she gives him a hand-knitted beanie, only to find out she gave everyone in the warehouse a hat.

Season 9, Episode 15 ("Couple's Discount")

In the finale Valentine's episode of the series, the office pairs off into couples to take advantage of a nail salon discount at the mall. This also marks one of Pam and Jim's more contentious episodes, as they're still dealing with the strain Jim's new job in Philadelphia is putting on their relationship. Jim nearly returns to Philly to avoid an argument with Pam, but ends up staying at her encouragement so they can fight together and work out their differences. And finally, Erin breaks up with Andy after he's gone for three months and officially begins her new relationship with Pete.

Season 9, Episodes 22 & 23 ("A.A.R.M")

In a favorite Jim and Pam moment from the entire series, during a time when Pam is doubting that she's good enough for Jim, he surprises her with a video made by the documentary film crew. It rounds up all of their best moments and concludes with a callback to Season 2's beloved "Christmas Party" episode when Jim took back the teapot note he wrote to Pam for her Secret Santa gift. When the video is over, he takes the note out of his pocket and finally gives it to Pam. It is the most romantic moment from The Office after nine seasons.

Season 9, Episodes 24 & 25 ("Finale")

Seeing as both parts of the finale are dedicated to Dwight and Angela's wedding after nine seasons of their quirky on-and-off relationship, it had to make the list.

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