Family photos are traditionally awkward, especially when these families choose to dress in similar clothes. I feel awkward for the friends of these families who receive the Holiday photograph and have to portend that the photo is sweet and endearing.
I typed in “Awkward family photos” into Google to find these photos. I would imagine it to be pretty damn embarrassing if this family knew that their family photo could be found in this way. Please post links to other awkward family photos in the comments sections. Now that everyone, including mothers and fathers in the Gen X generation, has a Facebook, there are now a plethora of these types of photos that are accessible to all.
Millennial Awkward Media 
hahahah yes! i love these. The tree one is always great.
I love how there’s a specific website for this stuff and co-created by a Midd kid no less. I will admit that I once spent a whole afternoon on AwkwardFamilyPhotos.com
& awkward family pet photos anyone? Not as great as the family photos, but still entertaining.
That’s awesome that a Middlebury alum created that website. Hilarious! Do families just look back at these photos and ask themselves, “what the fuck were we thinking?”