Awkward Moment Enjoyer Pillows

Add a touch of humor to your space with pillows designed for the awkward moment enjoyer. Soft and quirky, they remind everyone that it's okay to be a little uncomfortable sometimes.

All Products Prints T-Shirts Mugs Pillows

"Mr. Bream, it's time for you to put on a humiliating smock and let the doctor tell you about his fishing trip to Canada."

"Mr. Bream, it's time for you to put on a humiliating smock and let the doctor tell you about his fishing trip to Canada." mockup

"Mr. Bream, it's time for you to put on a humiliating smock and let the doctor tell you about his fishing trip to Canada."

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

"Blind dates can be awkward so I'll break the ice first. . . my colonoscopy took forever this morning."

"Blind dates can be awkward so I'll break the ice first. . . my colonoscopy took forever this morning." mockup

"Blind dates can be awkward so I'll break the ice first. . . my colonoscopy took forever this morning."

from $19.00

Showbiz Awards

from $19.00

"Oh, ah, sorry!"

from $19.00

'Fancy you doing a curtsey and she being a non-serving royal, you big dope!'

'Fancy you doing a curtsey and she being a non-serving royal, you big dope!' mockup

'Fancy you doing a curtsey and she being a non-serving royal, you big dope!'

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

"Do you have a boyfriend?"

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

"You and your daft inventions."

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

"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

Waiter does not want to see customer make bubbles in his wine.

Waiter does not want to see customer make bubbles in his wine. mockup

Waiter does not want to see customer make bubbles in his wine.

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

"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

"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

"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

"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

"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

"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

"Don't make eye-contact, don't make eye-contact..."

"Don't make eye-contact, don't make eye-contact..." mockup

"Don't make eye-contact, don't make eye-contact..."

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

Speed Dating Disasters

from $19.00

"I'm sensing an awkward presence." mockup

"I'm sensing an awkward presence."

from $19.00

"Say these things, don't think them!" mockup

"Say these things, don't think them!"

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

'By the way Adrian, it unfastens at the front.'

'By the way Adrian, it unfastens at the front.' mockup

'By the way Adrian, it unfastens at the front.'

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

"Are you blushing?!"

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

Awkward Moment Enjoyer Pillows Collection

Awkward Moment Enjoyer Mugs

Explore our collection of mugs for awkward moment enjoyers—funny, witty, and perfect for brightening up your mornings with a smile.

Awkward Moment Enjoyer Prints

Browse our prints for awkward moment enjoyers—humorous and relatable artwork that adds personality and wit to your decor.

Awkward Moment Enjoyer T-Shirts

Check out our T-shirt selection for awkward moment enjoyers—comfortable, humorous, and designed to showcase your love for life's funny, imperfect side.