20 Hysterically Cringeworthy Family Photos

awkward family photos

No matter how hard you try to look put together, wearing matching outfits, and smile just right, most family photos turn out slightly awkward.

Sure, there are exceptions to every rule, but more often than not, you’ll find something amusingly out-of-place about every portrait that hangs in your home. From a photobomber to cringe-worthy wardrobe choices, these 20 awkward family photos are sure to make you laugh… but not in a mean way. All are beautiful… in their own way.

1. “This is my second cousin ‘Jessica’ who happens to be engaged to the man holding the heart. The Cupid here is her brother. This is the engagement photo they used in their wedding invitation.”


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2. Sometimes, not everyone is onboard with the whole ‘matching outfits’ concept.


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3. This dad always managed to be so hip with the fashion trends…


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4. Someone didn’t get the silly photo memo.


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5. This great grandmother was super excited when she landed in Hawaii.


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6. “The whole family went for church directory photos and the photographer decided to be ‘creative’ with us. My husband is very much alive and well, but this photo screams ‘Dad is dead!'”

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7. There’s so much to unpack here, we don’t know where to start.


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8. Gang’s all here!


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9. Guess who’s the black sheep.


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10. This makes me slightly uncomfortable.


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11. What? How? What is happening?


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12. The family dogs hate making eye contact with one another… but this timing is too perfect.


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13. When your puppet is a part of the family.


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14. “This was from a family trip to Universal Studios in 1976. I was obsessed with monsters. I made my poor family wait in line for this ‘family style’ photo op with the werewolf. The photographer told us to put our arms around him.”

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15. That feeling when your whole family kisses at midnight on New Year’s Eve but you wisely decline.

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16. Why they each have kittens in their pockets… we’ll never know.


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17. This is what happens when Grandma tries to fix Dad’s unhappy face, but she doesn’t know how to use Photoshop.


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18. “Fine. If you don’t want to be in it, then just stay over there.”


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19. Whatever you say.


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20. There are just… so, so many things to talk about. Where to start?


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At the end of the day, though, no matter how awkward your photos are, family is the biggest blessing. Tell them you’re thankful for them today by sharing this story with them!

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