Awkward, Hilarious, and Unforgettable: A Christmas Photoshoot to Remember

This past Christmas, we found ourselves in Michigan at my sister-in-law’s house, and what better way to celebrate than with an intentionally awkward photoshoot? As a gift to my mother-in-law, my wife and her sister put on matching denim and black shirts, channeled their inner 90s glamour-shot energy, and fully committed to the bit. The result? A collection of gloriously cringey, absolutely perfect photos.

The setup was just as DIY as the concept. We found the cheesiest black background with Christmas trees and taped it up against the house—yes, right there in the driveway. You can even see a bit of the house and pavement in some of the shots, which honestly makes them even better. It’s all part of the charm.

What made this shoot even more fun was the range of emotions we captured. Some shots are perfectly posed in all their awkward glory—forced smiles, stiff side-by-side stances, and exaggerated head tilts. But in between the staged moments, I caught some really great shots of just the two of them—laughing, being completely themselves, and even a few unexpectedly good portraits.

This whole thing was a blast to create, and it reminded me why I love photography so much. Whether it’s capturing polished branding images or a full-on joke photoshoot, the best moments are always the ones that show personality and connection.

Here are some of my favorite shots from the session. Hope they bring you as much joy as they brought us (and my mother-in-law, who now has these masterpieces to cherish forever).