33 Awkwardly Hilarious Family Photos of Weird & Funny

Awkward Family Photos. Vintage Pics. Oddball Relatives.

And You Think Your Family’s Weird?

Pull up your britches and hunker down for a humorous romp through a funny dump of hilarious awkward family photos. As strange and bizarre as these vintage family photos may appear, they’ll make you happy that you’re actually part of a crazy family that is far less awkward than it may seem. Enjoy.
 

1.  When you’re stuck between making your move and your next bowel movement.

2.  Roger wasn’t all about hard-core gaming and programming. He actually had a softer side.

3.  While Nancy demonstrated her mastering of “Hot Cross Buns” on the clarinet, impatient Karen just had to let her solo rip.

4.  Why you never get an Owen Mills family portrait taken just days before your son’s audition for a small part in The Ring Pt. III.

5.  When you stumble across that box of family photos hidden in your grandparent’s attic and there’s no way you’ll ever look your sweet Meemaw the same way again.

6.  When you’re on your way to Walmart and you realize you’re overdressed.

7.  One of the family photos that finally made me realize why Aunt Michelle was secretly referred to as “Coal Shovel Shelly.”

8.  Party in the back. A life of disappointment in the front.

9.  “I just want to rock and roll all night, and can I make you a sandwich, honey? You really should eat something. You’re so skinny.”

10.  The precise moment the LSD kicked in.

11.  It appears some people are handling the Corona Virus lockdown better than others.

12.  Lisa was hoping to win the superlative for “Best Har,” but she’s happy for just being recognized.

13.  Partying on a budget.

14.  Getting lost in the sweet, seductive sounds of the Bernie Kowalski Quartet.

15.  Dear Katie, your cat is dead. Love, Rigor Mortis.

16.  When you think you’ve captured a hilarious pic on the panorama setting before you realize it was never on the panorama setting.

17.  Gladys had all the style, glamour, and suitors she could handle. The only thing missing in her life was a vodka martini, straight up and neat.

18.  Kids prove every day that true style has no rules.

19.  Brush. Rinse. Spit. Eat a few more tin cans. Brush. Rinse. Spit…

20.  The Dickey sisters. Eager to change your attitude while you wait.

21.  The Orlov brothers, after their run-in with the Dickey sisters.

22.  Grandma before taking one more shovel of snow up her nose before heading off to Studio 54.

23.  True friends. You never forget the ones you’ve left behind.

24.  Pink lips. Pink eye.

25.  Life with an older sister. Ya know, the one that everyone says is “special?” Let’s see her connect with nature’s cuddly creatures like Snow White cover in bacon grease.

26.  Well, at least she’s following the leash law. My guess is she didn’t curb him properly.

27.  “Incommmmming!”

28.  I just want to know what’s going on underneath the blanket.

29.  Some heavy shit just went down at the cabin in the woods.

30.  “So you come to me asking a favor yet my pool water is cold and you’ve done nothing to bring warmth to me and my family…”

31.  When you realize it’s your granddaughter that’s modeling in the following pic.

32.  High tide. High tech. High beams on high.

33.  Coping with 2020 and the fact that it’s your daughter posing in the photo above.

Thanks to Awkward Family Photos for some of the pics and lots of inspiration.