The Big Bang Theory presented one of the most awkward proposals in recent memory when a drunk and defeated Penny (her “big break” on NCIS was left on the cutting room floor) decided to make Leonard the luckiest nerd in California and propose. His shock mixed with her intoxication serves as inspiration for the episode’s title, “The Hesitation Ramification.”
2. Chandler & Monica (Friends)
Monica’s type-A personality may have set the stage for one of TV’s most romantic proposals, but it was Chandler who actually popped the question in the Friends Season 6 finale, “The One with the Proposal.”
3. Luke & Lorelai (Gilmore Girls)
A rare moment of quiet contemplation amid a flurry of daughter-drama let Lorelai’s heart do the talking when she proposed to Luke in the Gilmore Girls Season 5 finale, “A House Is Not a Home.”
4. Barney & Robin (How I Met Your Mother)
Even though we knew it was coming (thanks to the How I Met Your Mother Season 7 finale, which fast-forwarded to their wedding), Robin wasn’t the only one caught off guard by Barney’s rooftop proposal in “The Final Page.”
While The Playbook may have helped Barney sleep with more than 200 ladies, it also helped him score the mother of all women thanks to the last play he’ll ever run: “The Robin.”
5. Michael & Holly (The Office)
Proposing marriage amid a hail of sprinkler water while speaking like Yoda might sound like the worst proposal ever, but The Office used those two potential deal breakers to reinforce how perfect Holly was for Michael in the Season 7 episode, “Garage Sale.”
6. Trevor & Hilary (The Fresh Prince of Bel-Air)
“The Bigger, The Better” was Hilary’s motto, and that was exponentially true when it came to her boyfriend, Trevor, proposing. Sadly, his very public choice — while bungee jumping on the nightly news — fell extremely flat.
7. Derek & Meredith (Grey’s Anatomy)
Derek’s elaborate elevator proposal in this 2009 episode of Grey’s Anatomy not only transported the audience back to where it all began, but gave the dreamy doc a perfect platform to celebrate all Meredith’s accomplishments, both personal and professional, culminating in this very simple statement: “I’m not going to get down on one knee. I’m not going to ask a question. I love you, Meredith Grey, and I want to spend the rest of my life with you.”
Nothing ever seems to truly go right for Leslie Knope, making her unwavering optimism all the more enviable. And the universe rewarded her huge heart in the fifth season of Parks and Recreation when Ben Wyatt chose love over money and surprised his beloved by getting down on bended knee. Obviously, Knope said yes…after taking it all in…for a while.
9. Jim & Pam (The Office)
Surprise never felt as sweet as it did in the two-part Season 5 premiere of The Office’s as Jim’s attempt to stage the perfect proposal washed away when the ideal moment happened upon him … in a gas station halfway between Jim (in Scranton) and Pam (in NYC).
10. Matt & Julie (Friday Night Lights)
The Friday Night Lights series finale brought Matt’s relationship with Julie full circle as she accepted his characteristically awkward offer of m-m-m-marriage outside the Alamo Freeze.
11. Finn & Rachel (Glee)
After Mr. Schue’s beyond-over-the-top proposal to Emma in “Yes/No,” it was a relief to end the Glee episode with a much more understated affair as Finn asked for Rachel’s hand in marriage. While their engagement never led to a wedding, the love these two shared will forever be cherished by fans.
12. Harry & Charlotte (Sex and the City)
Charlotte didn’t have to invent a more charming story for her second marriage proposal as Harry’s heartfelt request was met with tears, and an implied “At Last!” from Sex and the City fans everywhere.
13. Matthew & Lady Mary (Downton Abbey)
Downton Abbey’s fated duo sealed their love with a steamy (for them) kiss in the snowy Season 2 finale.
14. Dexter & Rita (Dexter)
Watching Dexter realize the love he feigned for Rita and her family had become genuine was a watershed moment for the serial killer. It provided an equally significant moment for the series when Dex proposed in Season 3, telling Rita their love makes him “real.”
15. Booth & Bones (Bones)
Nothing says romance like processed, dehydrated beef. At least to Bones, who used the foodstuff as a conduit to express her feelings for Booth in this splendidly awkward proposal from Season 8.
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