Awkward Situation Enthusiast T-Shirts

Express their love for life's awkward moments with our fun t-shirts. Perfect for anyone who finds humor in social mishaps, these shirts are sure to spark smiles and conversations.

Awkward Situations Enthusiast T-Shirts Awkward Situation Aficionado T-Shirts Awkward Situation Enthusiasts T-Shirts Awkward Situations Aficionado T-Shirts Awkward Situation Enjoyer T-Shirts Awkward Situation Lover T-Shirts Awkward Situation Enjoyers T-Shirts Awkward Situation Admirer T-Shirts Awkward Situation Aficionados T-Shirts Quirky Situation Enthusiast T-Shirts

All Products Prints T-Shirts Mugs Pillows

Stan Mack's Real Life Funnies: Alumnae News

Stan Mack's Real Life Funnies: Alumnae News mockup

Stan Mack's Real Life Funnies: Alumnae News mockup

Stan Mack's Real Life Funnies: Alumnae News mockup

Stan Mack's Real Life Funnies: Alumnae News mockup

Stan Mack's Real Life Funnies: Alumnae News

from $19.00

'Ever get the feeling we've overstayed our welcome?'

'Ever get the feeling we've overstayed our welcome?' mockup

'Ever get the feeling we've overstayed our welcome?' mockup

'Ever get the feeling we've overstayed our welcome?' mockup

'Ever get the feeling we've overstayed our welcome?' mockup

'Ever get the feeling we've overstayed our welcome?'

from $19.00

'What I'm about to say, Miss Pomeroy, may shock and disgust you....'

'What I'm about to say, Miss Pomeroy, may shock and disgust you....' mockup

'What I'm about to say, Miss Pomeroy, may shock and disgust you....' mockup

'What I'm about to say, Miss Pomeroy, may shock and disgust you....' mockup

'What I'm about to say, Miss Pomeroy, may shock and disgust you....' mockup

'What I'm about to say, Miss Pomeroy, may shock and disgust you....'

from $19.00

"If you think the first half of this psychological test is intrusive, wait until you're grilled by me mother."

"If you think the first half of this psychological test is intrusive, wait until you're grilled by me mother." mockup

"If you think the first half of this psychological test is intrusive, wait until you're grilled by me mother." mockup

"If you think the first half of this psychological test is intrusive, wait until you're grilled by me mother." mockup

"If you think the first half of this psychological test is intrusive, wait until you're grilled by me mother." mockup

"If you think the first half of this psychological test is intrusive, wait until you're grilled by me mother."

from $19.00

"Look, I know Estella has a boyfriend. I would never try to break them up. But it's not illegal to text friends...and we're still friends..."

"Look, I know Estella has a boyfriend. I would never try to break them up. But it's not illegal to text friends...and we're still friends..." mockup

"Look, I know Estella has a boyfriend. I would never try to break them up. But it's not illegal to text friends...and we're still friends..." mockup

"Look, I know Estella has a boyfriend. I would never try to break them up. But it's not illegal to text friends...and we're still friends..." mockup

"Look, I know Estella has a boyfriend. I would never try to break them up. But it's not illegal to text friends...and we're still friends..." mockup

"Look, I know Estella has a boyfriend. I would never try to break them up. But it's not illegal to text friends...and we're still friends..."

from $19.00

'Check this out Henry, the stripper has arrived.'

'Check this out Henry, the stripper has arrived.' mockup

'Check this out Henry, the stripper has arrived.' mockup

'Check this out Henry, the stripper has arrived.' mockup

'Check this out Henry, the stripper has arrived.' mockup

'Check this out Henry, the stripper has arrived.'

from $19.00

"I'll tell you why she's got to come in - she's my wife!"

"I'll tell you why she's got to come in - she's my wife!" mockup

"I'll tell you why she's got to come in - she's my wife!" mockup

"I'll tell you why she's got to come in - she's my wife!" mockup

"I'll tell you why she's got to come in - she's my wife!" mockup

"I'll tell you why she's got to come in - she's my wife!"

from $19.00

Don't look down, just keep making eye contact...

Don't look down, just keep making eye contact... mockup

Don't look down, just keep making eye contact... mockup

Don't look down, just keep making eye contact... mockup

Don't look down, just keep making eye contact... mockup

Don't look down, just keep making eye contact...

from $19.00

"You seem to have won Dad over but Mum might be a bit of a problem."

"You seem to have won Dad over but Mum might be a bit of a problem." mockup

"You seem to have won Dad over but Mum might be a bit of a problem." mockup

"You seem to have won Dad over but Mum might be a bit of a problem." mockup

"You seem to have won Dad over but Mum might be a bit of a problem." mockup

"You seem to have won Dad over but Mum might be a bit of a problem."

from $19.00

'Y-y-yes-s....she's about your size.'

'Y-y-yes-s....she's about your size.' mockup

'Y-y-yes-s....she's about your size.' mockup

'Y-y-yes-s....she's about your size.' mockup

'Y-y-yes-s....she's about your size.' mockup

'Y-y-yes-s....she's about your size.'

from $19.00

"The interview was going great until she noticed on my c.v. that I was her ex husband."

"The interview was going great until she noticed on my c.v. that I was her ex husband." mockup

"The interview was going great until she noticed on my c.v. that I was her ex husband." mockup

"The interview was going great until she noticed on my c.v. that I was her ex husband." mockup

"The interview was going great until she noticed on my c.v. that I was her ex husband." mockup

"The interview was going great until she noticed on my c.v. that I was her ex husband."

from $19.00

"I didn't want to embarrass them by telling them I don't work here, so I told them it was a three-hour wait for a table instead."

"I didn't want to embarrass them by telling them I don't work here, so I told them it was a three-hour wait for a table instead." mockup

"I didn't want to embarrass them by telling them I don't work here, so I told them it was a three-hour wait for a table instead." mockup

"I didn't want to embarrass them by telling them I don't work here, so I told them it was a three-hour wait for a table instead." mockup

"I didn't want to embarrass them by telling them I don't work here, so I told them it was a three-hour wait for a table instead." mockup

"I didn't want to embarrass them by telling them I don't work here, so I told them it was a three-hour wait for a table instead."

from $19.00

'Hi there!... I know, that you know, that you know me from somewhere. But I'm not going to remind you, because I'm enjoying your look of excruciating embarrassment far too much!'

'Hi there!... I know, that you know, that you know me from somewhere. But I'm not going to remind you, because I'm enjoying your look of excruciating embarrassment far too much!' mockup

'Hi there!... I know, that you know, that you know me from somewhere. But I'm not going to remind you, because I'm enjoying your look of excruciating embarrassment far too much!' mockup

'Hi there!... I know, that you know, that you know me from somewhere. But I'm not going to remind you, because I'm enjoying your look of excruciating embarrassment far too much!' mockup

'Hi there!... I know, that you know, that you know me from somewhere. But I'm not going to remind you, because I'm enjoying your look of excruciating embarrassment far too much!' mockup

'Hi there!... I know, that you know, that you know me from somewhere. But I'm not going to remind you, because I'm enjoying your look of excruciating embarrassment far too much!'

from $19.00

'I appreciate your being a pal to me, Dad, but double-dating is just going too far.'

'I appreciate your being a pal to me, Dad, but double-dating is just going too far.' mockup

'I appreciate your being a pal to me, Dad, but double-dating is just going too far.' mockup

'I appreciate your being a pal to me, Dad, but double-dating is just going too far.' mockup

'I appreciate your being a pal to me, Dad, but double-dating is just going too far.' mockup

'I appreciate your being a pal to me, Dad, but double-dating is just going too far.'

from $19.00

'I was going to say see me afterwards Miss Jones but of course you are seeing me afterwards.'

'I was going to say see me afterwards Miss Jones but of course you are seeing me afterwards.' mockup

'I was going to say see me afterwards Miss Jones but of course you are seeing me afterwards.' mockup

'I was going to say see me afterwards Miss Jones but of course you are seeing me afterwards.' mockup

'I was going to say see me afterwards Miss Jones but of course you are seeing me afterwards.' mockup

'I was going to say see me afterwards Miss Jones but of course you are seeing me afterwards.'

from $19.00

"Did I just butt-dial my booty call?"

"Did I just butt-dial my booty call?" mockup

"Did I just butt-dial my booty call?" mockup

"Did I just butt-dial my booty call?" mockup

"Did I just butt-dial my booty call?" mockup

"Did I just butt-dial my booty call?"

from $19.00

"Hi, there. I'm Dick. Are you seeing anyone?"

"Hi, there. I'm Dick. Are you seeing anyone?" mockup

"Hi, there. I'm Dick. Are you seeing anyone?" mockup

"Hi, there. I'm Dick. Are you seeing anyone?" mockup

"Hi, there. I'm Dick. Are you seeing anyone?" mockup

"Hi, there. I'm Dick. Are you seeing anyone?"

from $19.00

"So, have you two been doing anything reproductive?"

"So, have you two been doing anything reproductive?" mockup

"So, have you two been doing anything reproductive?" mockup

"So, have you two been doing anything reproductive?" mockup

"So, have you two been doing anything reproductive?" mockup

"So, have you two been doing anything reproductive?"

from $19.00

"Honestly, I didn't know your wife was in the shower."

"Honestly, I didn't know your wife was in the shower." mockup

"Honestly, I didn't know your wife was in the shower." mockup

"Honestly, I didn't know your wife was in the shower." mockup

"Honestly, I didn't know your wife was in the shower." mockup

"Honestly, I didn't know your wife was in the shower."

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.' mockup

'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.' mockup

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

from $19.00

'We've got a special this week on nose hairs!'

'We've got a special this week on nose hairs!' mockup

'We've got a special this week on nose hairs!' mockup

'We've got a special this week on nose hairs!' mockup

'We've got a special this week on nose hairs!' mockup

'We've got a special this week on nose hairs!'

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... mockup

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

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

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

from $19.00

Bad Interview Technique

Bad Interview Technique mockup

Bad Interview Technique mockup

Bad Interview Technique mockup

Bad Interview Technique mockup

Bad Interview Technique

from $19.00

"I hope you don't call that a party face."

"I hope you don't call that a party face." mockup

"I hope you don't call that a party face." mockup

"I hope you don't call that a party face." mockup

"I hope you don't call that a party face." mockup

"I hope you don't call that a party face."

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." mockup

"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." mockup

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

from $19.00

Time management office worker

Time management office worker mockup

Time management office worker mockup

Time management office worker mockup

Time management office worker mockup

Time management office worker

from $19.00

"It's not what you think."

"It's not what you think." mockup

"It's not what you think." mockup

"It's not what you think." mockup

"It's not what you think." mockup

"It's not what you think."

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?" mockup

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

"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

The Consequences of an Interrupted Shower.

The Consequences of an Interrupted Shower. mockup

The Consequences of an Interrupted Shower. mockup

The Consequences of an Interrupted Shower. mockup

The Consequences of an Interrupted Shower. mockup

The Consequences of an Interrupted Shower.

from $19.00

Top Ten Elevator Hits of All Time

Top Ten Elevator Hits of All Time mockup

Top Ten Elevator Hits of All Time mockup

Top Ten Elevator Hits of All Time mockup

Top Ten Elevator Hits of All Time mockup

Top Ten Elevator Hits of All Time

from $19.00

'Today's unwilling nude model is Ralph.'

'Today's unwilling nude model is Ralph.' mockup

'Today's unwilling nude model is Ralph.' mockup

'Today's unwilling nude model is Ralph.' mockup

'Today's unwilling nude model is Ralph.' mockup

'Today's unwilling nude model is Ralph.'

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!" mockup

"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!" 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." mockup

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

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

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

from $19.00

"Ah guys, before you push any buttons can I just check my calculator?"

"Ah guys, before you push any buttons can I just check my calculator?" mockup

"Ah guys, before you push any buttons can I just check my calculator?" mockup

"Ah guys, before you push any buttons can I just check my calculator?" mockup

"Ah guys, before you push any buttons can I just check my calculator?" mockup

"Ah guys, before you push any buttons can I just check my calculator?"

from $19.00

"And with that being said Polly became dinner." "Polly wanna cracker?" "Polly wanna piece of yo mama's sweet behind." "Oh boy..."

"And with that being said Polly became dinner." "Polly wanna cracker?" "Polly wanna piece of yo mama's sweet behind." "Oh boy..." mockup

"And with that being said Polly became dinner." "Polly wanna cracker?" "Polly wanna piece of yo mama's sweet behind." "Oh boy..." mockup

"And with that being said Polly became dinner." "Polly wanna cracker?" "Polly wanna piece of yo mama's sweet behind." "Oh boy..." mockup

"And with that being said Polly became dinner." "Polly wanna cracker?" "Polly wanna piece of yo mama's sweet behind." "Oh boy..." mockup

"And with that being said Polly became dinner." "Polly wanna cracker?" "Polly wanna piece of yo mama's sweet behind." "Oh boy..."

from $19.00

Awkward Situation Enthusiast T-Shirts Collection

Awkward Situation Enthusiast Mugs

Explore our collection of mugs celebrating awkward moments—great for anyone who loves to laugh at life's social slip-ups.

Awkward Situation Enthusiast Pillows

Discover cozy pillows that celebrate the charm of awkward moments—ideal for anyone who appreciates humor in everyday life.

Awkward Situation Enthusiast Prints

Browse our prints that highlight the humor of awkward situations—great for decorating spaces with wit and personality.