Dating Disaster Expert Gifts

Looking for a gift that honors the wild, unpredictable world of love? Our collection for dating disaster experts features witty, humorous items that celebrate those hilarious, cringe-worthy romantic moments. Whether they’ve turned a first date into a comedy show or survived a breakup with humor, these playful gifts bring a smile to anyone who’s experienced love’s chaos. From quirky mugs to fun t-shirts, find something that laughs along with their romantic adventures and keeps the smile of resilience shining bright.

All Products Prints T-Shirts Mugs Pillows

"My love for you knows no bounds, Trish."

"My love for you knows no bounds, Trish." mockup

"My love for you knows no bounds, Trish."

from $19.00

'Big date tonight, but I've just shed an antler: Do you have superglue?'

'Big date tonight, but I've just shed an antler: Do you have superglue?' mockup

'Big date tonight, but I've just shed an antler: Do you have superglue?'

from $19.00

Boyfriend of the Month.

from $19.00

The Stages of Wine

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

'Yeah, but this time she just said no -- there wasn't any hysterical laughter!'

'Yeah, but this time she just said no -- there wasn't any hysterical laughter!' mockup

'Yeah, but this time she just said no -- there wasn't any hysterical laughter!'

from $19.00

'Standing on tiptoe waving your claw may attract a crab, but it certainly doesn't woo me.'

'Standing on tiptoe waving your claw may attract a crab, but it certainly doesn't woo me.' mockup

'Standing on tiptoe waving your claw may attract a crab, but it certainly doesn't woo me.'

from $19.00

"I've had my eye on you for some time" mockup

"I've had my eye on you for some time"

from $19.00

"Not so fast, Casanova! I want to get to know a man and his intentions better before I allow him to accompany me to the cinema!"

"Not so fast, Casanova! I want to get to know a man and his intentions better before I allow him to accompany me to the cinema!" mockup

"Not so fast, Casanova! I want to get to know a man and his intentions better before I allow him to accompany me to the cinema!"

from $19.00

'Wow!... Look at the personality on her!'

'Wow!... Look at the personality on her!' mockup

'Wow!... Look at the personality on her!'

from $19.00

Tom prepares for his hot date.

from $19.00

"I knew I should've swiped left." mockup

"I knew I should've swiped left."

from $19.00

Colin had heard that women liked honesty in men.

Colin had heard that women liked honesty in men. mockup

Colin had heard that women liked honesty in men.

from $19.00

'Well thank you Igor!! I spend all night making small talk with the blonde and Mr. googly eyes has to show up!!'

'Well thank you Igor!! I spend all night making small talk with the blonde and Mr. googly eyes has to show up!!' mockup

'Well thank you Igor!! I spend all night making small talk with the blonde and Mr. googly eyes has to show up!!'

from $19.00

'It was disgusting, Sheila...Our first date, and he pulls out his endpin!'

'It was disgusting, Sheila...Our first date, and he pulls out his endpin!' mockup

'It was disgusting, Sheila...Our first date, and he pulls out his endpin!'

from $19.00

"I'm a simple man, really."

from $19.00

"Your blind dates is at the bar - I'll upgrade you to a table by the getaway door."

"Your blind dates is at the bar - I'll upgrade you to a table by the getaway door." mockup

"Your blind dates is at the bar - I'll upgrade you to a table by the getaway door."

from $19.00

Babe magnet

from $19.00

'No thanks! Playing doctor is how my folks ended up getting married.'

'No thanks! Playing doctor is how my folks ended up getting married.' mockup

'No thanks! Playing doctor is how my folks ended up getting married.'

from $19.00

He couldn't put his finger on it but something told Colin the date wasn't going well.

He couldn't put his finger on it but something told Colin the date wasn't going well. mockup

He couldn't put his finger on it but something told Colin the date wasn't going well.

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."

from $19.00

"When you said on your profile you are 'loyal and affectionate' I expected something a little different."

from $19.00

"My name is Adam and your name is Eve and that I think is a good starting point for a relationship between us!"

"My name is Adam and your name is Eve and that I think is a good starting point for a relationship between us!" mockup

"My name is Adam and your name is Eve and that I think is a good starting point for a relationship between us!"

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.'

from $19.00

Do you know what girls want?

from $19.00

"I'm still in recovery for my perfectionism."

"I'm still in recovery for my perfectionism." mockup

"I'm still in recovery for my perfectionism."

from $19.00

"So now I guess I'll have to meet your friends."

"So now I guess I'll have to meet your friends." mockup

"So now I guess I'll have to meet your friends."

from $19.00

Geek Todd Jones strikes out with his 3000th wiman to take over third place on the all time geek strikeout list.

Geek Todd Jones strikes out with his 3000th wiman to take over third place on the all time geek strikeout list. mockup

Geek Todd Jones strikes out with his 3000th wiman to take over third place on the all time geek strikeout list.

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.'

from $19.00

Tom suspected the date wasn't going as well as he'd hoped when she asked for the Emergency exit.

Tom suspected the date wasn't going as well as he'd hoped when she asked for the Emergency exit. mockup

Tom suspected the date wasn't going as well as he'd hoped when she asked for the Emergency exit.

from $19.00

"How come I always pick the bastards?" mockup

"How come I always pick the bastards?"

from $19.00

'I went out with that new hunk in Sales last night. Great closer!'

'I went out with that new hunk in Sales last night. Great closer!' mockup

'I went out with that new hunk in Sales last night. Great closer!'

from $19.00

Twenty thousand leagues out of his league

Twenty thousand leagues out of his league mockup

Twenty thousand leagues out of his league

from $19.00

"I'm not single I'm 'between relationships'."

"I'm not single I'm 'between relationships'." mockup

"I'm not single I'm 'between relationships'."

from $19.00

Dating Disaster Expert Gifts Collection

Dating Disaster Expert Mugs

Explore our collection of mugs that perfectly capture the humor of dating disasters—ideal for slow mornings and laughs over coffee.

Dating Disaster Expert Pillows

Discover pillows that celebrate the humor of love’s mishaps—cue up cozy comfort with a side of laughter about dating disasters.

Dating Disaster Expert Prints

Browse our playful prints celebrating love’s chaos—perfect for adding humor and personality to any space.

Dating Disaster Expert T-Shirts

Check out our funny t-shirts designed for dating disaster experts—lighthearted, witty, and perfect for turning love’s chaos into style.