40 Funny Family Photos That Turn Awkward Into Art

Family photos can feel weird and awkward, yet they’re almost always a hoot. Let’s face it, posing with your family isn’t exactly the most natural thing, but it’s crucial to snap those memories once in a while. You’d be amazed at how quickly everyone ages – it’s like one day you’re all fresh-faced, and the next, you’re wondering who invited the wise old wizard to the party.

My family has gone decades without an awkward family photo shoot, and honestly, I kinda wish we had a yearly visual diary. Tracing our fashion disasters and hairstyle horrors would be hilarious over the years. Imagine the laughs around the dinner table, pointing at a photo and saying, “Remember when Dad thought mullets were cool?” Family photo throwbacks: embarrassing, yes, but pure comedy gold.


1. “For My Father’s 88th Birthday, We Took This Traditional Japanese Portrait Of Our Crime Syndicate Family”

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2. “An Authentic Family Portrait”

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3. “When Your Pocket Square Is Your Family Hamster For The Christmas Photo”

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4. “My Wife Looked So Obnoxiously Thin 24 Hours After Giving Birth That I Joked That I Looked Like The One Who Had Just Given Birth. So We Decided To Swap For A Funny Photo”

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5. “A Friend Had A Family Photo Taken”

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6. “Family Photo Gone Wrong”

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7. “I Set The Timer On The Camera And Then Fell Running To Get In The Photo. This Is My Family’s Reaction”

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8. “Annual Family Photo”

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9. “Channeling The Winter Of 1980. This Was Our Family’s Holiday Photo Last Year. We Need To Have A Sense Of Humor In Life And Not Take Ourselves Too Seriously”

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10. “We Just Wanted A Nice Family Photo”

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11. “That Family Picture Where I Had My Hand In My Pants”

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12. “Yes This Is Really My Childhood Family Photo”

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13. “My Hilarious Father (With The Magazine) And My Grandfather, Grandmother And Uncle At His Bar Mitzvah In 1972”

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14. “We Finally Got A Family Photo That Represents Us”

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15. “My Current Relationship Status: Emily”

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16. “My Mom Missed A Group Photo So She Offered To Photoshop Herself In”

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17. “We’re Good Parents I Swear”

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18. “My Friend’s Family’s Christmas Card”

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19. “My Grandparents And My Mother In The Front. 1967, Tokyo, Japan”

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20. “How To Get Everyone In The Family Picture”

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21. “10 Years Ago It Was Our First Family Photo, It Looked Like We Stole Someone’s Kid”

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22. “Yet Another Year As The Last Unmarried In The Family”

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23. “Family Photos”

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24. “Go Ahead I Dare You To Show Me Your More Awkward Family Photo”

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25. “Nothing But Aquanet”

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26. “Nothing Says 1980’s Like My Friend’s Family Photo”

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27. “This Is As 1988 As It Gets”

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28. “My Family Was Not Particularly Photogenic In The 80s”

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29. “For Our First Family Portrait We Told My Younger Sister To Make Sure To Not Blink, And To Smile Nice And Big. All Of The Pictures Came Out Like This”

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30. “My Nephew Wasn’t Down For Our Wizard Of Oz Halloween Theme”

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31. “Family Thanksgiving 1990. What A Time To Be Alive”

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32. “Friend Paid To Get A Nice Family Portrait Done”

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33. “Happy Halloween From Our Beautiful Family To Yours”

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34. “Graduating Today From Temple University After 15 Years Of Working Full-Time And Balancing My Life. Attempted To Take A Family Photo At Graduation”

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35. “Family Photo From Last Fall: We Had To Physically Restrain My Little Brother And When He Finally Got To Jump, The Photographer Caught This Gem”

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Nate

Nate Armbruster

When he's not doomscrolling Twitter or writing for Pleated-Jeans, Nate Armbruster writes jokes—and then tells them on stage as a stand-up comedian, where he can watch audiences (hopefully) laugh in real-time.