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14 People Share Their Most Awkward Attempts At Flirting

I don’t flirt because I suck at it. You’re about to meet 14 people who flirted and failed miserably. After reading many of these, I feel very good about my decision to not flirt. 14. SQUIRT!!! I went to Israel on birthright. towards the beginning of the trip, we had a 5 hour bus ride through the desert. I was pretty sleep deprived...

9 People Share How Weird It Is When An Ex Marries A Family Member

Love is strange. And sometimes love gets kicked out the front door, sneaks in the back door and starts living in the room next to you. Go grab a drink, kick back and marvel at these 9 wonderfully weird tales of all those exes just wouldn’t go away. In fact, they stayed for good. 9. Okay, I Need More Explanation My great grandmother had...

Jimmy Fallon Wants to Know: What’s the Most Awkward Breakup You’ve Ever Had

I mean, this one is kind of a no-brainer – after all, what breakup isn’t at least a little bit awkward ? That said, these 15 people who replied to Jimmy Fallon’s hashtag game really took breaking up and awkwardness to a whole new level. Do not, under any circumstances, try this at home, people. #15. I would personally call this the...

7 Glamour Shots That Might Have Missed the Mark

Remember Glamour Shots? Thankfully, it doesn’t matter – either way, you’re in for a soft-filtered, super-teased treat: #7. Grandma Glamour Photo Credit: Awkward Family Photos/Hillary “My twin sister and I took glamour shots with our grandmother. We loved her, but sometimes she had some weird ideas.” #6. What’s the...

5 Impossible Celebrity Look-Alikes

It’s actually not that crazy that someone might look like a celebrity. Lots of people look like other people. Not that it makes it any less cool. I ran into my doppelgänger at a high school party back in 1997, and I know that if we had cell phones back then, I’d have definitely taken a selfie. But these ones are particularly special,...

5 Acid Washed, Banged up Photos from the 90s

The 90s were an awkward time. The bangs were high, and fashion was low. The denim was acid washed, and often tight-rolled or tapered. For instance: #5. Acid Washed Photo Credit: Awkward Family Photos/Alex So much awesome and awkward going on here. But she’s got nothing on the next dude when it comes to acid/stone-washed denim: #4. Pocket...

11 Insane Reasons Why Employees Called in to Work

You’ve done it, I’ve done it… we’ve all done it: called in to work because we just couldn’t deal with today. Because today sometimes sucks. When this inevitably happens, we politely lie to our employers about feeling ill, having a family emergency or any number of completely reasonable, rational excuses that...

These Five Dogs Are the Most Normal Part of These Photos

Dogs can really throw a bone into the works when you’re trying to take a photo. But, it’s not always their fault. In fact, when it comes to being awkward, humans have it on lock. And, the dogs might be the only normal part of these 5 photos: #5. “When I do it, it’s cute. When you do it…” Photo Credit: Awkward...

5 Times Dogs Put The “Awkward” in Awkward Family Photos

Getting the family together for a photo is difficult enough. Especially when kids are involved. Add dogs into the mix, and things can get awkward: #5. You brought me to a meadow, and you want me to stay still?! Photo Credit: Awkward Family Photos/Velurkiraptor “My sister and her fiance took their dog with them for engagement...