Dealing With Dating Disappointments T-Shirts

Find t-shirts with witty slogans and relatable designs that speak to the ups and downs of love. Great for anyone trying to stay positive after dating mishaps.

Coping With Disappointment T-Shirts Dating Woes T-Shirts Dating Struggles T-Shirts Dating Misadventures T-Shirts Frustration In Dating T-Shirts Bad Date Experiences T-Shirts Awkward Daters T-Shirts Awkward Date Moments T-Shirts Comedically Frustrated Dater T-Shirts Dating Misadventure Appreciation T-Shirts

All Products Prints T-Shirts Mugs Pillows

"If Neil could only be half the man he is in his texts..."

"If Neil could only be half the man he is in his texts..." mockup

"If Neil could only be half the man he is in his texts..." mockup

"If Neil could only be half the man he is in his texts..." mockup

"If Neil could only be half the man he is in his texts..." mockup

"If Neil could only be half the man he is in his texts..."

from $19.00

Life is for the birds.

Life is for the birds. mockup

Life is for the birds. mockup

Life is for the birds. mockup

Life is for the birds. mockup

Life is for the birds.

from $19.00

'Eloise! Come back! I was just going to show you some of the equipment we use in veterinary school...'

'Eloise! Come back! I was just going to show you some of the equipment we use in veterinary school...' mockup

'Eloise! Come back! I was just going to show you some of the equipment we use in veterinary school...' mockup

'Eloise! Come back! I was just going to show you some of the equipment we use in veterinary school...' mockup

'Eloise! Come back! I was just going to show you some of the equipment we use in veterinary school...' mockup

'Eloise! Come back! I was just going to show you some of the equipment we use in veterinary school...'

from $19.00

'He's narrating it, I just know it.'

'He's narrating it, I just know it.' mockup

'He's narrating it, I just know it.' mockup

'He's narrating it, I just know it.' mockup

'He's narrating it, I just know it.' mockup

'He's narrating it, I just know it.'

from $19.00

'Crabs, sharks, octopi...'

'Crabs, sharks, octopi...' mockup

'Crabs, sharks, octopi...' mockup

'Crabs, sharks, octopi...' mockup

'Crabs, sharks, octopi...' mockup

'Crabs, sharks, octopi...'

from $19.00

'When it comes to romance, Sherlock doesn't have a clue!'

'When it comes to romance, Sherlock doesn't have a clue!' mockup

'When it comes to romance, Sherlock doesn't have a clue!' mockup

'When it comes to romance, Sherlock doesn't have a clue!' mockup

'When it comes to romance, Sherlock doesn't have a clue!' mockup

'When it comes to romance, Sherlock doesn't have a clue!'

from $19.00

"Oh, for butter curls on ice!"

"Oh, for butter curls on ice!" mockup

"Oh, for butter curls on ice!" mockup

"Oh, for butter curls on ice!" mockup

"Oh, for butter curls on ice!" mockup

"Oh, for butter curls on ice!"

from $19.00

'You're afraid of commitment, aren't you?'

'You're afraid of commitment, aren't you?' mockup

'You're afraid of commitment, aren't you?' mockup

'You're afraid of commitment, aren't you?' mockup

'You're afraid of commitment, aren't you?' mockup

'You're afraid of commitment, aren't you?'

from $19.00

'What happens when your little sister misses her toy money?'

'What happens when your little sister misses her toy money?' mockup

'What happens when your little sister misses her toy money?' mockup

'What happens when your little sister misses her toy money?' mockup

'What happens when your little sister misses her toy money?' mockup

'What happens when your little sister misses her toy money?'

from $19.00

'But enough about my interiority, how about you?'

'But enough about my interiority, how about you?' mockup

'But enough about my interiority, how about you?' mockup

'But enough about my interiority, how about you?' mockup

'But enough about my interiority, how about you?' mockup

'But enough about my interiority, how about you?'

from $19.00

"So this is what we call a 'red flag'..."

"So this is what we call a 'red flag'..." mockup

"So this is what we call a 'red flag'..." mockup

"So this is what we call a 'red flag'..." mockup

"So this is what we call a 'red flag'..." mockup

"So this is what we call a 'red flag'..."

from $19.00

"Some people think accountants are just boring number crunchers but statistics show that 43% of 456 people covering 56% of the total demographic were 67% sure that we're really a lot of fun!"

"Some people think accountants are just boring number crunchers but statistics show that 43% of 456 people covering 56% of the total demographic were 67% sure that we're really a lot of fun!" mockup

"Some people think accountants are just boring number crunchers but statistics show that 43% of 456 people covering 56% of the total demographic were 67% sure that we're really a lot of fun!" mockup

"Some people think accountants are just boring number crunchers but statistics show that 43% of 456 people covering 56% of the total demographic were 67% sure that we're really a lot of fun!" mockup

"Some people think accountants are just boring number crunchers but statistics show that 43% of 456 people covering 56% of the total demographic were 67% sure that we're really a lot of fun!" mockup

"Some people think accountants are just boring number crunchers but statistics show that 43% of 456 people covering 56% of the total demographic were 67% sure that we're really a lot of fun!"

from $19.00

"Smile! It's for the women I've dated scrapbook!"

"Smile! It's for the women I've dated scrapbook!" mockup

"Smile! It's for the women I've dated scrapbook!" mockup

"Smile! It's for the women I've dated scrapbook!" mockup

"Smile! It's for the women I've dated scrapbook!" mockup

"Smile! It's for the women I've dated scrapbook!"

from $19.00

The Adventures of Morton

The Adventures of Morton mockup

The Adventures of Morton mockup

The Adventures of Morton mockup

The Adventures of Morton mockup

The Adventures of Morton

from $19.00

'You asked her to go out with you?', 'Yes, but she says there's a lengthy approval process.'

'You asked her to go out with you?', 'Yes, but she says there's a lengthy approval process.' mockup

'You asked her to go out with you?', 'Yes, but she says there's a lengthy approval process.' mockup

'You asked her to go out with you?', 'Yes, but she says there's a lengthy approval process.' mockup

'You asked her to go out with you?', 'Yes, but she says there's a lengthy approval process.' mockup

'You asked her to go out with you?', 'Yes, but she says there's a lengthy approval process.'

from $19.00

'My Mother makes me wear this - It's my name and address in case I get lost.'

'My Mother makes me wear this - It's my name and address in case I get lost.' mockup

'My Mother makes me wear this - It's my name and address in case I get lost.' mockup

'My Mother makes me wear this - It's my name and address in case I get lost.' mockup

'My Mother makes me wear this - It's my name and address in case I get lost.' mockup

'My Mother makes me wear this - It's my name and address in case I get lost.'

from $19.00

"Would you ask the chef to hurry? We're running out of conversation."

"Would you ask the chef to hurry? We're running out of conversation." mockup

"Would you ask the chef to hurry? We're running out of conversation." mockup

"Would you ask the chef to hurry? We're running out of conversation." mockup

"Would you ask the chef to hurry? We're running out of conversation." mockup

"Would you ask the chef to hurry? We're running out of conversation."

from $19.00

"Why do you always fall for these totally unobtainable types?"

"Why do you always fall for these totally unobtainable types?" mockup

"Why do you always fall for these totally unobtainable types?" mockup

"Why do you always fall for these totally unobtainable types?" mockup

"Why do you always fall for these totally unobtainable types?" mockup

"Why do you always fall for these totally unobtainable types?"

from $19.00

"I walked up to this hot girl with two drinks in my hands, and she turned to me, smiled and said, are you lost, Grandpa? The toilets are back there."

"I walked up to this hot girl with two drinks in my hands, and she turned to me, smiled and said, are you lost, Grandpa? The toilets are back there." mockup

"I walked up to this hot girl with two drinks in my hands, and she turned to me, smiled and said, are you lost, Grandpa? The toilets are back there." mockup

"I walked up to this hot girl with two drinks in my hands, and she turned to me, smiled and said, are you lost, Grandpa? The toilets are back there." mockup

"I walked up to this hot girl with two drinks in my hands, and she turned to me, smiled and said, are you lost, Grandpa? The toilets are back there." mockup

"I walked up to this hot girl with two drinks in my hands, and she turned to me, smiled and said, are you lost, Grandpa? The toilets are back there."

from $19.00

'Can you suggest a wine to go with someone who's going to be hitting the road as soon as this date is over?'

'Can you suggest a wine to go with someone who's going to be hitting the road as soon as this date is over?' mockup

'Can you suggest a wine to go with someone who's going to be hitting the road as soon as this date is over?' mockup

'Can you suggest a wine to go with someone who's going to be hitting the road as soon as this date is over?' mockup

'Can you suggest a wine to go with someone who's going to be hitting the road as soon as this date is over?' mockup

'Can you suggest a wine to go with someone who's going to be hitting the road as soon as this date is over?'

from $19.00

I'm an investor. My star sign is predator.

I'm an investor. My star sign is predator. mockup

I'm an investor. My star sign is predator. mockup

I'm an investor. My star sign is predator. mockup

I'm an investor. My star sign is predator. mockup

I'm an investor. My star sign is predator.

from $19.00

"The date was a disaster: he grew up with pirates you see, so I couldn't understand half of what he was saying..."

"The date was a disaster: he grew up with pirates you see, so I couldn't understand half of what he was saying..." mockup

"The date was a disaster: he grew up with pirates you see, so I couldn't understand half of what he was saying..." mockup

"The date was a disaster: he grew up with pirates you see, so I couldn't understand half of what he was saying..." mockup

"The date was a disaster: he grew up with pirates you see, so I couldn't understand half of what he was saying..." mockup

"The date was a disaster: he grew up with pirates you see, so I couldn't understand half of what he was saying..."

from $19.00

"I miss the days when people were ashamed to admit they met online."

"I miss the days when people were ashamed to admit they met online." mockup

"I miss the days when people were ashamed to admit they met online." mockup

"I miss the days when people were ashamed to admit they met online." mockup

"I miss the days when people were ashamed to admit they met online." mockup

"I miss the days when people were ashamed to admit they met online."

from $19.00

"But the restraining order was totally temporary."

"But the restraining order was totally temporary." mockup

"But the restraining order was totally temporary." mockup

"But the restraining order was totally temporary." mockup

"But the restraining order was totally temporary." mockup

"But the restraining order was totally temporary."

from $19.00

'Hand me your issue of esquire. I have a hot date.'

'Hand me your issue of esquire. I have a hot date.' mockup

'Hand me your issue of esquire. I have a hot date.' mockup

'Hand me your issue of esquire. I have a hot date.' mockup

'Hand me your issue of esquire. I have a hot date.' mockup

'Hand me your issue of esquire. I have a hot date.'

from $19.00

"My blind date?! Oh, he was Arabian alright, but he was a camel..."

"My blind date?! Oh, he was Arabian alright, but he was a camel..." mockup

"My blind date?! Oh, he was Arabian alright, but he was a camel..." mockup

"My blind date?! Oh, he was Arabian alright, but he was a camel..." mockup

"My blind date?! Oh, he was Arabian alright, but he was a camel..." mockup

"My blind date?! Oh, he was Arabian alright, but he was a camel..."

from $19.00

I always strike out on blind dates

I always strike out on blind dates mockup

I always strike out on blind dates mockup

I always strike out on blind dates mockup

I always strike out on blind dates mockup

I always strike out on blind dates

from $19.00

"Well, would you like to tell me anything about you now or shall I carry on where I left off?"

"Well, would you like to tell me anything about you now or shall I carry on where I left off?" mockup

"Well, would you like to tell me anything about you now or shall I carry on where I left off?" mockup

"Well, would you like to tell me anything about you now or shall I carry on where I left off?" mockup

"Well, would you like to tell me anything about you now or shall I carry on where I left off?" mockup

"Well, would you like to tell me anything about you now or shall I carry on where I left off?"

from $19.00

Earlier that day. Cheapskate Ernie bought discounted love potion 8.

Earlier that day. Cheapskate Ernie bought discounted love potion 8. mockup

Earlier that day. Cheapskate Ernie bought discounted love potion 8. mockup

Earlier that day. Cheapskate Ernie bought discounted love potion 8. mockup

Earlier that day. Cheapskate Ernie bought discounted love potion 8. mockup

Earlier that day. Cheapskate Ernie bought discounted love potion 8.

from $19.00

"Normally I like men who talk with their hands."

"Normally I like men who talk with their hands." mockup

"Normally I like men who talk with their hands." mockup

"Normally I like men who talk with their hands." mockup

"Normally I like men who talk with their hands." mockup

"Normally I like men who talk with their hands."

from $19.00

Dealing With Dating Disappointments T-Shirts Collection

Dealing With Dating Disappointments Mugs

Hop over to our mugs collection for more witty and reassuring designs perfect for those navigating love’s disappointments.

Dealing With Dating Disappointments Pillows

Browse cozy pillows featuring humorous or supportive messages to comfort someone healing from romantic setbacks.

Dealing With Dating Disappointments Prints

View our prints that humorously or thoughtfully illustrate the journey of love and disappointment, adding a touch of personality to their space.