Awkward Family Photos (24 pics)

  • Category: Pics  |
  • 8 Apr, 2025  |
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Nostalgia hits differently when browsing cringe-worthy family portraits frozen in time. Unintentional hilarity ensues as outdated fashion trends clash with forced smiles and awkward poses. Despite (or perhaps because of) their cheesiness, these snapshots capture genuine moments of familial love and connection. Laugh along at memories immortalized in hilariously retro glory.

"My Brother, Chris’s 1998 Senior Picture. He Really Loved Batman"



1 Awkward Family Photos (24 pics)

"This Picture Was Taken At My Daughter’s Preschool Photo Day. I Think The Photographer Thought Having Her Hold A Flower Would Make For A Really Cute And Innocent Picture"


2 Awkward Family Photos (24 pics)

"My Family Took This Photo For Our Baptist Church Directory In The Late 90s. It Was A Bit Of A Scandal But In Our Defense, Men In Black Had Just Come Out"


3 Awkward Family Photos (24 pics)

"My Dad Liked To Balance Me On One Hand And Sometimes He Used Props"


4 Awkward Family Photos (24 pics)

"This Is A Picture Of My Grandpa, Aunt, And Uncle On Christmas Morning. You Can See They Are Full Of Cheer And Excitement For The Holiday"


5 Awkward Family Photos (24 pics)

"During Our ‘Perfect’ Beach Photo Shoot, My Oldest Son Jumped On My Back, Propelling My Infant Son Out Of My Arms (As My Middle Son Looked On In Amusement)"



6 Awkward Family Photos (24 pics)

"I Played Keyboard In Elementary School Band And School Photos Were Sometimes Full Of The Rock And Roll That Comes With The Territory"


7 Awkward Family Photos (24 pics)

"In Hindsight, My Freddy Krueger Shirt Probably Wasn’t Appropriate Attire For My Cousin's Holy Communion"


8 Awkward Family Photos (24 pics)

"This Was Supposed To Be A Cute Photo Of Me And My Newborn Son"


9 Awkward Family Photos (24 pics)

"This Is A Photo Of Me Faceplanting Into The Ground After What Looks Like My Sister Pushed Me Off The Top"


10 Awkward Family Photos (24 pics)

"This Family Photo Hung In My Pop And Gram’s House For Years. To Say They Didn’t Like My Aunt’s Ex-Husband May Have Been An Understatement"



11 Awkward Family Photos (24 pics)

"My Aunt’s Wedding Pictures With Her Bridesmaids And Flower Girl"


12 Awkward Family Photos (24 pics)

"The Last (And Arguably The Greatest) Professional Portrait Studio Photo Of My Husband And His Family"


13 Awkward Family Photos (24 pics)

"I Was The Punk Rock / Artist Of The Family"


14 Awkward Family Photos (24 pics)

"Me, My Husband And Our 2 Children – It’s Our 2021 Holiday Photo And No Matter How We Tried To Entertain Our Son, He Wasn’t Having It"


15 Awkward Family Photos (24 pics)

"This Is My Parents On Their Wedding Day In 1975. She Was Always On His Mind Then And She Still Is Today"



16 Awkward Family Photos (24 pics)

"I Think The Stuffed Animal Possessed My Older Brother When He Was 7 Months Old In 1973"


17 Awkward Family Photos (24 pics)

"My Swiss-American Great-Grandparents On Their 40th Wedding Anniversary Sometime In The 40’s. So Happy Together"


18 Awkward Family Photos (24 pics)

"The Church Directory Photographer Created This Of Me And My Mom And My Parents Bought A 5×7. I Always Hated It"


19 Awkward Family Photos (24 pics)

"Australia, 1979 Mother’s Day. We Fought And We Needed To Take Photos To Remember"


20 Awkward Family Photos (24 pics)

"Yes, This Is My Family Photo"



21 Awkward Family Photos (24 pics)

"We Just Wanted One Picture With All The Cousins"


22 Awkward Family Photos (24 pics)

"This Was Taken In 1976 On Our Country’s Bicentennial. I’m The Little Guy That Resembles A Puppet"


23 Awkward Family Photos (24 pics)

"This Was The Only Bench Around To Rest After A Long Hike, So We Sat And Took Five"


24 Awkward Family Photos (24 pics)

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