Any jerk with a diamond in his pocket can propose at the site of a first date. A real geek will recreate that same first date in Chrono Trigger while seamlessly integrating shared memories into the game's story. According to the proposer's original YouTube description, he was careful to incorporate heartfelt personal anecdotes without tipping her off before the proposal. And it worked. His writing fits surprisingly well with the rest of the game. Honestly, if Magic First Date Mountain was snuck into your copy of Chrono Trigger, you probably wouldn't notice that it doesn't belong. Well, except at the end when a knight guy proposes to you and calls you by some lady's name.
With a hugely devoted fan base and a kick-ass co-op mode for loving couples to get their puzzle on, Portal was inevitably going to lend itself to a geeky proposal video eventually. What we didn't expect was for the eventual Aperture-themed question-popping to look this insanely polished.
Gary Hudston hired a pair of skilled level designers to help him create a series of drop-dead gorgeous Portal 2 puzzle rooms, and even got the actual voice actress of GlaDOS involved to provide a few witty marriage-and-neurotoxin-themed quips throughout. The resulting level is so well-executed, it looks like it belongs in the game proper. In fact, maybe it should have been, just so we could see Gary's hand in marriage go to whichever Portal addict conquered these puzzles first.
First off, this couple gets bonus points for their classy attire. They are undoubtedly the most dressed-up people ever to play Earthbound. But more importantly, this isn't just a videogame proposal for the sake of a videogame proposal. This couple clearly loves them some Earthbound. We only know them (well, Internet know them) for about a minute before finding out that he developed a crush on her while she was posting on Starman.net, an Earthbound fan site. And her favorite part of the game just happens to be the section with giant light-up scrolling text. Giant light-up scrolling text that can be hacked and edited to say anything. Like "Will You Marry Me?" If there was ever a better candidate for an Earthbound proposal, I'd like to meet her. Because I'd like to propose to her myself.
Other proposals on this list might be more touching or sentimental, but let's be honest: if you wanted touching and sentimental, you wouldn't have proposed to the love of your life with a videogame. You'd have taken them to a candlelit dinner or a tropical island like the big sappy baby you are. And you'd be a fraction as cool as Borderlands superfan Ben was when he enlisted Gearbox Software to help him propose to his fellow skag-slaying spouse-to-be.
Gearbox, never willing to pass up an opportunity to be totally badass, did Ben a solid by creating this custom proposal video starring series icon Claptrap, and damn is it good. It takes some solid writing to top GlaDOS in the hilariously unsentimental AI department, but Claptrap manages to steal the #1 slot here by selling an endearing proposal even while roasting the young lovers, tearing into Tora's weird choice of nickname and questioning Ben's sexual health. Let this be a lesson to all you nerds in love this Valentine's Day: losers get roses and walks on the beach. Winners go home and get roasted by chatty post-apocalyptic robots.