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The Worst Dating/Relationship Fails of 2011

The Worst Dating/Relationship Fails of 2011

You think your love life was in the dumps this year? Waittillya read these unfortunate incidents of dating and relationships gone way wrong. So wrong, they went past wrong, back to okay, and back to wrong again. Cheers to 2012, a year of dating your not-brother, non-awkward kissing, and boyfriends who don't stalk their own girlfriends. Yes, we can!

The Worst Marriage Proposal of 2011 goes to... this guy who, in one proposal, makes a terrible kitten reference, a terrible cupcake reference, and a terrible Cinnabon reference, all set to the sound of a terrible song. Maybe we shouldn’t be surprised he got totally dissed. Dude, what are you doing?

The Worst Dating Advice came from... the Millionaire Matchmaker’s Patti Stanger! Thanks for your anti-curl agenda and your bat-poo crazy rules about girls never ever paying for food, at least not with money. But no thanks.

The Worst Wedding/Marriage/Divorce was... Kim Kardashian’s obviously. Who would have thought she could win all of these in one year? Kim’s such an overachiever.

The Worst You May-Now-Kiss-The-Bride Kiss goes to... these people. We can’t even watch this the whole way through, but we are assuming it doesn’t get any better. This is just the worst, unless the kids are trying to be funny. And in that case, they are hilarious.

The Rudest Flower Diss was... Madonna. If a guy brings you flowers, it’s not hard. You say thank you. Don’t say you loathe them, Madonna. We don’t care if you do. No really, we don’t care. Keep it to yourself. Next time that guy is going to bring you a flaming bag of dog poo. On your door step.

The Worst Dater goes to... this woman, who used to earn $1200 a month going on dates. Or maybe we’re just jealous. Think about how many of those little Starbucks cake pop things you can buy with $1200! YUM! Or... yuck. This woman is awful.

The Worst Break-Up Retribution goes to... Houston’s Toni Jo Silvey, who called her ex, Peter Main, 1,001 times in three months. But that’s just the semi-weird part. The really weird part was when she shattered several of his windows with a tire iron and then a 5-foot sword.

The Worst Boyfriend of 2011 was... the guy who stalked his own girlfriend. Creeeeeeppppppyyyyyyy.

The Worst Breaker-Upper of 2011 was... This guy, who wrote almost an entire novel to dump a girl he'd gone out with just a few times. Stop at 6 paragraphs next time, bro.

The Worst Online Dating Site of 2011 was..., which only lets in... everyone say it with me... beautiful people! But oops, this year, a virus allowed 30,000 ugly people to slip through the cracks, onto the site, where they were told they were beautiful enough to date in’s exclusive dating pool when in fact they were so not. When the error was realized, the rejects were kicked off the site. offered them counseling services, because they’re just great like that. More like Amirite?!

Worst Blind Date of 2011 was... the brother and the sister who probably almost made out with each other, or maybe even almost touched butts. Fortunately they found out they were related before anything dreadful happened.

Did you have any terrible dating/relationship stories this year? Let's get them out of our system, forget they happened and move on! Kris Humphries who?

Related post: Worst First Date Conversations

Topics: Life
Tags: dating, romance, awkward situations

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