Romantic Episodes Of The Office To Watch This Valentine’s Day

On Valentine’s Day, many couples opt to watch romantic movies, go out for a fancy dinner, or stick to other “activities” on this day of love. But my husband and I always rewatch different romantic episodes from The Office in addition to a nice dinner at home and other activities. Not only is it our favorite show, but there’s something relatable and lovely about every single romantic relationship in the series, whether that’s Michael and Holly, Dwight and Angela, or of course, Jim and Pam.

“There’s a lot of beauty in ordinary things. Isn’t that kind of the point?”

From Jim confessing his love to Pam on “Casino Night,” to Michael finally asking Holly out and ignoring Jan’s request, or Dwight finally realizing he truly loves Angela and then asking her to marry him after almost running over her with his car, there are so many special, romantic, and of course hilarious moments throughout the nine seasons of this incredible show.

So skip the fancy dinner and sappy movie, grab a charcuterie board, your favorite beverages and your favorite person, and cuddle up on the couch to binge a few of these 15 The Office Valentine’s Day episodes this year. Though they aren’t all Valentine’s Day-specific, they definitely have the romance factor you’ll be looking for on this day of love.

Romantic Episodes Of The Office To Watch On Valentine’s Day

• Season 2, Episode 1: “The Dundies”: I love this episode because there’s something so sweet and exciting about that surprise kiss Pam gives Jim — even if it’s because she let her inhibitions go after drinking too many margaritas at Chili’s, where she not only felt God, but also isn’t allowed to go back to ever again. That melted ice making “second drink” will make you kiss your true love every time.
• Season 2 , Episode 16: “Valentine’s Day”: Though unfortunately you begin to see just how badly Roy really treats Pam when he offers to give her “the best sex of her life” for Valentine’s Day, this is the first episode where we see a potentially blossoming romance between Dwight and Angela as she gives him that iconic bobblehead of himself. “The best gift he’d ever received.”

• Season 2, Episode 22: “Casino Night”: When Michael hosts a Casino Night in the warehouse for a fundraiser, sparks continue to fly between Jim and Pam. After Roy leaves Pam for the evening, and tells Jim to “Keep an eye on her,” boy does he ever. When Jim comes up to Pam to presumably tell her that he’s thinking about transferring to Stamford, he tells her he’s in love with her. After she tells him “she can’t,” we later find Pam back at Jim’s desk. Jim enters and as she starts to say something, he grabs her and pulls her in for the best kiss ever. Swoon.
• Season 3 Episode 23: “Beach Games”: This episode is romantic to me, because of the importance of Pam standing up for herself and finally sort of telling Jim what she wants. The look on his face when she tells him that she misses “their friendship” is perfection and is the beginning of a foundation to their romantic relationship.
• Season 3 Episodes 24 & 25: “The Job”: When Jim swoops in after not accepting the job at corporate to ask Pam on a date when she’s confessing that “it’s OK” they’ve never got the timing right and they’ll always be friends? Iconic and tear-inducing. Especially when Pam looks at the camera with happy tears in her eyes, bites her lip ecstatically, and asks, “I’m sorry, what was the question?”
• Season 4, Episodes 18 & 19: “Goodbye, Toby”: This episode is romantic because you really see how great Holly and Michael are for each other right off the bat. And I guess that awkward proposal by Andy to Angela with fireworks was romantic, too? Even though it ruined Jim’s planned proposal for Pam and broke Dwight.
• Season 5, Episodes 1 & 2: “Weight Loss”: Obviously, this one is romantic because Jim proposes to Pam. It was perfect — even though it was in a gas station parking lot, in the rain.

• Season 5, Episode 4: “The Baby Shower”: Audiences seethed when Jan told Michael to not date Holly in her typical controlling psychopath fashion. The best part of this entire cringe episode featuring Ass-turd, is when Michael silently walks into Holly’s office and sweetly just gives her a hug, bringing her to tears. And he finally asks her out.
• Season 5, Episode 16: “Blood Drive”: Even though it’s Michael’s first Valentine’s Day since he and Holly split up, he ends up having a sweet encounter with a woman while donating blood and it brings him a moment of joy on the holiday — until he passes out. He finds her glove and spends the rest of the afternoon trying to figure out who it belongs to and hosts a special Valentine’s Day party at the office for all the singles. So Jim and Pam go out on a double date with Phyllis and Bob Vance, Vance Refrigeration, where they unfortunately hear them having sex in the bathroom.
• Season 5, Episode 28: “Company Picnic”: While on its surface this episode may not seem romantic with Dwight being characteristically competitive during a volleyball match with Dunder Mifflin corporate, this episode is where Jim and Pam find out she’s pregnant. The look on Jim’s face when he hears and the tears of joy and shock he has when he calls Dwight to tell them to “call in the subs” for the game gets me every single time without fail. I cry right along with him.

• Season 6, Episodes 4 & 5: “Niagara – Parts 1 & 2”: Though it doesn’t go as planned — like most weddings — this two-part episode is of course still romantic. From Jim and Pam taking mental pictures to Jim cutting his tie off, and then the couple eloping to the Niagara Falls cruise to tie the knot in a secret ceremony, this is the perfect episode. It’s the episode where the famous line, “I bought those tickets the day I saw that YouTube video. I knew we'd need a backup plan. The boat was actually Plan C, the church was Plan B, and Plan A was marrying her a long, long time ago. Pretty much the day I met her.”
• Season 6, Episodes 17 & 18: “The Delivery”: While the actual act of childbirth may not necessarily be romantic to most people, the way Jim reacts when Pam won’t go to the hospital to have Cece is so sweet and concerned, I find it incredibly romantic — especially when he finds out she’s having a girl. There’s also that horribly cringe moment when he’s trying to convince her not to have the baby in the office and Michael is righthere so close to them, but when Jim says, “If anyone can do this, you can do this. Pam, I'm scared. I'm real scared. The best news is, we're going to have a baby today. A really awesome baby.”
• Season 7, Episode 15: “PDA”: If you can handle the potential ick factor of insane amounts of PDA, then this episode is definitely romantic because hooray! Holly and Michael are back together! And it’s also Valentine’s Day, and Jim and Pam have too much champagne at lunch and end up trying to find a place to have sex in the office. They tell the documentary crew they went for a walk, but we all know what happened.

• Season 7, Episode 18: “Garage Sale”: Michael’s proposal to Holly is in this romantic episode and it is so “them” and so romantic and sweet. There’s the walkthrough of the office showcasing all of their firsts, then the candles in the annex, and her weirdly going through the line of folks from the office and denying their marriage proposals. And then the fire sprinklers going off all over everyone and Michael getting down on his knees (and Holly does, too) and he proposes to her like Yoda because of course he does. The romance and sweet feelings are cut short when Michael informs everyone they’re moving to Colorado.
• Season 9, Episode 15: “Couples Discount”: With their marriage troubles due to miscommunication and Jim living in Philly part time for his new job, Jim and Pam don’t seem to be in sync anymore. He’s home for Valentine’s Day in this episode, and after an awkward Valentine’s Day lunch with Brian the boom guy (who was there for Pam when Jim wasn’t), Jim decides to head back to Philly early. Pam chases after him and tells him she thinks they should fight in the hopes that it saves their marriage. Jim says, “Put your dukes up Beesley,” and they leave the office for some very much needed dialogue.
• Season 9, Episode 23: “A.A.R.M”: Not only does Jim talk it out with Dwight about how Angela is the one for him and she’s always been the one, but Jim plays a video for Pam that he had the film crew make of their relationship throughout the entire series, proving to her that not only is she “enough,” but she is “everything.” I believe this is also the episode when Dwight almost runs Angela over with his car to tell her he loves her and he proposes to her in the street.
• Season 9, Episodes 24 & 25: “Finale”: Of course the finale has to be on this list because Dwight and Angela finally get married, and Pam surprises Jim by being supportive in his new career and putting their house on the market to sell so they can all move to Philly.

Where Can You Stream The Office?

Unless you’re old AF millennials like my husband and I and already have the complete series on DVD (that’s right, DVD, not even Blu-Ray) then you can head over to Peacock and binge your favorite The Office episodes right there. If you don’t want to deal with ads and commercials, you’ll have to purchase a Peacock subscription for $4.99. For unlimited ad-free access to The Office and all of your other NBC faves? Worth it.