10 Biggest Valentine’s Day Disasters In TV That Prove It Could Be Worse

With Valentine’s Day approaching, there are plenty of great examples in TV that prove that the celebration of love and romance could be a lot worse. It’s quite common to see a TV show broadcast a holiday special episode, and while Valentine’s Day isn’t at the top of the priority order, there have still been some brilliant Valentine’s Day episodes. While many spend the day with their significant other in bliss, this isn’t always the case for some TV characters.

Like any holiday, Valentine’s Day has the potential for all kinds of chaos. Trying to find a significant other is a difficult feat on its own, let alone taking into account gifts, dates, and even love triangles in the process. While many people don’t experience the same hectic Valentine’s Days that are seen in TV shows, it’s worth remembering that the most romantic day of the year could be a lot worse.

10 Monica And Chandler’s Homemade Gifts

Friends: Season 6, Episode 17

“The One With Unagi” saw Monica (Courteney Cox) and Chandler (Matthew Perry) into the depths of their relationship and celebrating Valentine’s Day. The two decide to exchange homemade gifts, and while Chandler’s response to this made a lot of sense, Monica’s didn’t. Considering Monica was the over-planner, wanting everything to be perfect, it was odd to see her not put a huge, romantic effort in. Although she is a little lazy and gifts Chandler a sock bunny creation of Phoebe’s (Lisa Kudrow), Monica’s gift is significantly worse.

Receiving an old mixtape that was originally a gift for Chandler from his ex, Janice (Maggie Wheeler), and hearing her nasal voice while the two slow danced was an embarrassing ordeal for Monica. Although it did distract from the fact that she’d not made her own gift, as well as the fact that the sock bunny idea was already rejected by Chandler over fears that Monica would find out it wasn’t homemade, it doesn’t excuse how careless Chandler was in his gift giving. Even though Monica and Chandler’s relationship was successful in general, this Valentine’s Day was quite the flop.

9 The Longest Day Of Pam’s Life

The Office: Season 2, Episode 16

The Office‘s first Valentine’s Day episode was a solemn affair for Pam (Jenna Fischer), only half-aware of the fact she was with the wrong person. Although Pam had been with Roy (David Denman) for a while at this point, she still held out hope that he’d bring her a small gift, despite the agreement that planning their wedding put a strain on their finances. Instead, she got to spend the day ferrying various presents for Phyllis (Smith) from Bob Vance (Bobby Ray Shafer) and other characters in The Office across the room.

With each gift’s arrival, Pam’s disappointment continued to plummet, hoping at least one would be for her. Clueless Roy hadn’t thought of this, however, and upon arriving upstairs from the warehouse to take her home, tells Pam that evening she’ll get “the best sex of her life” instead. Even though the promise of a night of lovemaking could be considered a gift, Pam deserved better, and Valentine’s Day shouldn’t have been such an afterthought for Roy, given how long the two had been together.

8 Liz And Drew’s First Date

30 Rock: Season 3, Episode 11

While Liz Lemon (Tina Fey) had quite the difficulty with relationships in 30 Rock, she managed to fit an entire one into a single evening with her first date with handsome Doctor, Drew (Jon Hamm). The date kicks off badly, with Liz accidentally exposing both her breast and her sitting on the toilet to Drew, but unfortunately for her, it only gets worse. She quickly ends up meeting Drew’s entire family, including his teenage daughter and ex-wife, before ending the evening at the hospital, meeting his siblings and mother.

However, poor Liz is pulled even further into Drew’s world. While meeting Drew’s terminally ill mother on her deathbed, she reveals to Liz that she’s actually his grandmother and his sister is his biological mother. Even though the two decide to continue dating after these events, with Liz having to awkwardly share the news of Drew’s parentage, it must have been a painful, full-on evening for what was supposed to be a first date.

7 Kevin’s Proposal To Robin

How I Met Your Mother: Season 7, Episode 16

One of Robin’s (Cobie Smulders) most heartbreaking moments in How I Met Your Mother involved her discovering that she was infertile. Despite being very sure about not ever wanting any kids, the news was still tough for Robin, as the option to have a child if she ever changed her mind was no longer available for her. Unfortunately, this ended up ruining her Valentine’s Day with Kevin (Kal Penn), who took the opportunity to propose.

Robin felt that she had to be honest with Kevin about her fertility, despite the concern that he’d not want to be with her once he’d found out. However, once Robin explained that she had no interest in being a mother, and expressed her doubts that one day Kevin would resent her for not giving him children, the two decided to end their relationship. Even though Robin knew, deep down, that the decision was for the best, it was easily her worst Valentine’s Day to date.

6 Andrew’s Jealousy Over Missy

Big Mouth: Season 3, Episode 1

Between Big Mouth seasons 2 and 3 came an extended Valentine’s Day special, which saw the various students of Bridgeton Middle celebrating romance. However, not everything was candy and rainbows, especially for Andrew (John Mulaney). Throughout the show, Andrew has an ongoing crush on Missy (Ayo Edebiri), but the character shifts into a possessive and manipulative ghost of himself upon learning of her involvement with Lars (Neil Casey). It all comes to a head at Lola’s (Nick Kroll) party, however, when Andrew heartlessly pulls Lars out of his wheelchair after a public rant, claiming that the boy can actually walk.

While “My Furry Valentine” saw some brilliant musical numbers, it doesn’t make up for the fact that Andrew ended up ruining the day for everyone. Not only was Missy horrifically embarrassed in front of her peers, with Andrew vocalizing that he had ownership over her, but she also had to watch her new boyfriend go through quite a traumatic experience. Although there have definitely been worse Valentine’s Days on TV, this was definitely one of the worst things Andrew ever did in Big Mouth and something that would be burned into Missy’s brain for the rest of her life.

5 A Bloody First Date

Supernatural: Season 5, Episode 14

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The Supernatural episode “My Bloody Valentine” saw a rather gorey first date for Russell (Andrew Halliwell) and Alice (Aili Storen). While their second date on Valentine’s Day went well, with the scene setting up the possibility of sex between the two, it quickly goes downhill when Alice suddenly bites Russell. The image of blood spreading across the room in a frenzy, with Alice influenced by the Horseman Famine and giving her cannibalistic tendencies, was one that won’t be forgotten easily.

3 Xander’s Failed Love Spell

Buffy The Vampire Slayer: Season 2, Episode 16

After Cordelia (Charisma Carpenter) ends things with Xander (Nicholas Brendon) on Valentine’s Day, the young man is determined to make her fall in love with him. However, his plan falls apart after he convinces a witch to perform a love spell, which draws in all of the women of Sunnydale except Cordelia. Xander then finds himself fighting off various women, including his best friends, Buddy (Sarah Michelle Gellar) and Willow (Alyson Hannigan).

While it must have been bad enough for Xander, especially as the only woman he wanted to love him back didn’t, he wasn’t the only member of the Scooby gang to experience a tough day. In an attempt to reverse the spell, yet another backfires, and Buffy gets turned into a rat. Even though Cordelia and Xander end the episode reuniting, it is definitely an ordeal that neither Buffy nor Xander will forget anytime soon.

2 Fighting Your Best Friend For The Same Girl

Community: Season 2, Episode 15

There were very few instances in Community in which audiences saw Abed (Danny Pudi) pursue a romantic interest, let alone someone Troy (Donald Glover) was interested in too. The two quickly take an interest in Greendale’s new librarian, Mariah (Maite Schwartz), and plan on inviting her to the upcoming Valentine’s dance. She agrees to go with both of them, in order to decide which she’s more interested in and would want to date further.

Despite enjoying both of their company, she ultimately chooses Troy. Although Abed is perfectly content with her decision, Troy breaks things off after she calls Abed “weird.” This episode is a great example of why Troy and Abed’s bromance trumps everything else in Community, and even though Abed understood Mariah’s decision, Troy’s platonic love for Abed was more important than a relationship with someone who didn’t understand his best friend.

1 Realizing Your Boyfriend Isn’t A Great Person

Parks And Recreation: Season 2, Episode 16

There’s no doubt that Leslie Knope (Amy Poehler) is the Queen of Valentine’s Day, but it’s a shame that her first with Justin (Theroux) went so badly. Always thinking of others, Leslie spends her day organizing an all-female celebration with her friends, showering them with thoughtful gifts. After hearing her mother, Marlene’s (Pamela Reed), first love story once again, Leslie then hatches a pan to reunite the two. Assisted by her boyfriend, Leslie tracks down Frank (John Larroquette) and brings him to the Valentine’s Day dance she’d organized for the local senior citizens, setting up his reunification with Marlene.

When things don’t go to plan between Marlene and Frank, Justin is surprised their Valentine’s Day plan failed. Leslie finds herself upset with his reaction, realizing that throughout the day, something wasn’t clicking between the two when Ron (Nick Offerman) points out that Justin cares more about orchestrating interesting stories to impress others, rather than making someone happy. These qualities are the complete opposite of Leslie’s, so it’s no surprise that she ends things shortly after this. Even though she enjoys the work, it is a shame that nobody treated her the way she treated everybody else that day.