Uncomfortable Moment Enthusiasts Pillows

Add a cozy, humorous touch to any space with pillows that celebrate the hilarity of uncomfortable moments. Perfect for bedrooms or lounges where laughter is the best therapy.

All Products Prints T-Shirts Mugs Pillows

Funeral - So how are things otherwise? mockup

Funeral - So how are things otherwise?

from $19.00

Showbiz Awards

from $19.00

"Oh, ah, sorry!"

from $19.00

'When you asked me over for a home-cooked meal, I assumed you'd be making it.'

'When you asked me over for a home-cooked meal, I assumed you'd be making it.' mockup

'When you asked me over for a home-cooked meal, I assumed you'd be making it.'

from $19.00

"I was a lot happier with the elephant in the room."

"I was a lot happier with the elephant in the room." mockup

"I was a lot happier with the elephant in the room."

from $19.00

Always an awkward moment when you meet a Dung Beetle...

Always an awkward moment when you meet a Dung Beetle... mockup

Always an awkward moment when you meet a Dung Beetle...

from $19.00

"You and your daft inventions."

from $19.00

'Eh...our costume party was last Saturday!'

'Eh...our costume party was last Saturday!' mockup

'Eh...our costume party was last Saturday!'

from $19.00

"Do you have a boyfriend?"

from $19.00

"Such a cute doggie! And I'll bet you make the cutest poopies too, don't you?"

"Such a cute doggie! And I'll bet you make the cutest poopies too, don't you?" mockup

"Such a cute doggie! And I'll bet you make the cutest poopies too, don't you?"

from $19.00

"OK, I know that this is borderline inappropriate, but just hear me out ..."

"OK, I know that this is borderline inappropriate, but just hear me out ..." mockup

"OK, I know that this is borderline inappropriate, but just hear me out ..."

from $19.00

"Let's start with a couple of glasses of water and if that goes well I'll order two coffees."

"Let's start with a couple of glasses of water and if that goes well I'll order two coffees." mockup

"Let's start with a couple of glasses of water and if that goes well I'll order two coffees."

from $19.00

"I suppose I should have let a few minutes elapse between declaring my love for you and announcing that I also loved lobster."

"I suppose I should have let a few minutes elapse between declaring my love for you and announcing that I also loved lobster." mockup

"I suppose I should have let a few minutes elapse between declaring my love for you and announcing that I also loved lobster."

from $19.00

"Humiliation is a very important part of the the process, Mr. Keifer."

"Humiliation is a very important part of the the process, Mr. Keifer." mockup

"Humiliation is a very important part of the the process, Mr. Keifer."

from $19.00

"Don't panic, she'll be back. We lock the washroom windows from the outside."

"Don't panic, she'll be back. We lock the washroom windows from the outside." mockup

"Don't panic, she'll be back. We lock the washroom windows from the outside."

from $19.00

"Ignore the screams, sir. I'll get a new fork."

"Ignore the screams, sir. I'll get a new fork." mockup

"Ignore the screams, sir. I'll get a new fork."

from $19.00

'Look. . . for the last time, I'm not playin' 'footsie' with you!'

'Look. . . for the last time, I'm not playin' 'footsie' with you!' mockup

'Look. . . for the last time, I'm not playin' 'footsie' with you!'

from $19.00

Baldo's How to Be Uncool: No. 5. Forget how hot the coffee is while you're thinking how cool you look sitting in a coffee shop.

Baldo's How to Be Uncool: No. 5. Forget how hot the coffee is while you're thinking how cool you look sitting in a coffee shop. mockup

Baldo's How to Be Uncool: No. 5. Forget how hot the coffee is while you're thinking how cool you look sitting in a coffee shop.

from $19.00

"Good evening, I'm your date. Let me begin by saying I'm sorry I'm late, I'm sorry I'm bald and I'm sorry I'm short."

"Good evening, I'm your date. Let me begin by saying I'm sorry I'm late, I'm sorry I'm bald and I'm sorry I'm short." mockup

"Good evening, I'm your date. Let me begin by saying I'm sorry I'm late, I'm sorry I'm bald and I'm sorry I'm short."

from $19.00

As years of unspoken tension surfaced, Trunky refused to raise his hand like a coward.

As years of unspoken tension surfaced, Trunky refused to raise his hand like a coward. mockup

As years of unspoken tension surfaced, Trunky refused to raise his hand like a coward.

from $19.00

"If that girl sent over a double cappuccino, maybe you should go talk to her!"

"If that girl sent over a double cappuccino, maybe you should go talk to her!" mockup

"If that girl sent over a double cappuccino, maybe you should go talk to her!"

from $19.00

"I'm sensing an awkward presence." mockup

"I'm sensing an awkward presence."

from $19.00

"Are you blushing?!"

from $19.00

Speed Dating Disasters

from $19.00

"On a scale of 1-10, how painfully awkward is this?"

"On a scale of 1-10, how painfully awkward is this?" mockup

"On a scale of 1-10, how painfully awkward is this?"

from $19.00

"You have to get up early tomorrow, too? We have so much in common!"

"You have to get up early tomorrow, too? We have so much in common!" mockup

"You have to get up early tomorrow, too? We have so much in common!"

from $19.00

"I think that one is a little too honest."

"I think that one is a little too honest." mockup

"I think that one is a little too honest."

from $19.00

A close encounter of the awkward kind mockup

A close encounter of the awkward kind

from $19.00

'It's our first date. You don't know me well enough to ask if I'm getting enough fiber.'

'It's our first date. You don't know me well enough to ask if I'm getting enough fiber.' mockup

'It's our first date. You don't know me well enough to ask if I'm getting enough fiber.'

from $19.00

"Let’s try another one. Jerry blinked, Kate’s giving Jon the finger, and Jess is choking."

"Let’s try another one. Jerry blinked, Kate’s giving Jon the finger, and Jess is choking." mockup

"Let’s try another one. Jerry blinked, Kate’s giving Jon the finger, and Jess is choking."

from $19.00

"Of course mating is natural. It's just not the kind of thing you want to see your parents doing."

"Of course mating is natural. It's just not the kind of thing you want to see your parents doing." mockup

"Of course mating is natural. It's just not the kind of thing you want to see your parents doing."

from $19.00

Uncomfortable Moment Enthusiasts Pillows Collection

Uncomfortable Moment Enthusiasts Mugs

Explore our collection of mugs crafted for uncomfortable moment enthusiasts and start every morning with a laugh.

Uncomfortable Moment Enthusiasts Prints

Browse our humorous prints designed for uncomfortable moment enthusiasts, adding a witty touch to your living space.

Uncomfortable Moment Enthusiasts T-Shirts

Discover playful t-shirts perfect for anyone who loves to make light of awkward situations — perfect for casual wear and making statements.