Awkward First Dater Pillows

Offer comfort and humor with our cozy pillows designed for the awkward first dater. Ideal for relaxing after a nerve-wracking date, these pillows feature witty sayings and adorable illustrations.

All Products Prints T-Shirts Mugs Pillows

"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?"

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."

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...'

from $19.00

"I've been out of the dating scene a long time. Is kissing still a thing?"

"I've been out of the dating scene a long time. Is kissing still a thing?" mockup

"I've been out of the dating scene a long time. Is kissing still a thing?"

from $19.00

"How sweet, your hand is trembling." mockup

"How sweet, your hand is trembling."

from $19.00

In Desperate Straits.

from $19.00

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

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

from $19.00

"Your profile didn't mention you being a chewer."

from $19.00

'Would you like to come in for a rejection?'

'Would you like to come in for a rejection?' mockup

'Would you like to come in for a rejection?'

from $19.00

"Monsieur has just ordered a vasectomy..."

"Monsieur has just ordered a vasectomy..." mockup

"Monsieur has just ordered a vasectomy..."

from $19.00

"Don't worry, I'm a doctor."

from $19.00

"I guess your reputation for tipping has preceded you!"

"I guess your reputation for tipping has preceded you!" mockup

"I guess your reputation for tipping has preceded you!"

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

'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!'

from $19.00

"Tell your date you're a vegetarian before he orders that expensive gourmet dinner."

"Tell your date you're a vegetarian before he orders that expensive gourmet dinner." mockup

"Tell your date you're a vegetarian before he orders that expensive gourmet dinner."

from $19.00

"Oh, for butter curls on ice!"

from $19.00

"If it's all the same to you, Kevin, I'd like to continue observing the six-foot-rule."

"If it's all the same to you, Kevin, I'd like to continue observing the six-foot-rule." mockup

"If it's all the same to you, Kevin, I'd like to continue observing the six-foot-rule."

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?'

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?'

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!"

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'..."

from $19.00

"I like long walks on the beach and beautiful sunsets, too...but who are you?"

"I like long walks on the beach and beautiful sunsets, too...but who are you?" mockup

"I like long walks on the beach and beautiful sunsets, too...but who are you?"

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!"

from $19.00

Nethead strip: Dates

from $19.00

She hated first dates. She always ended up sounding desperate.

She hated first dates. She always ended up sounding desperate. mockup

She hated first dates. She always ended up sounding desperate.

from $19.00

'You two will have lots in common - you share the same anxiety neurosis.'

'You two will have lots in common - you share the same anxiety neurosis.' mockup

'You two will have lots in common - you share the same anxiety neurosis.'

from $19.00

The Adventures of Morton

from $19.00

But enough about me, let's talk about my job.

But enough about me, let's talk about my job. mockup

But enough about me, let's talk about my job.

from $19.00

'I've never felt like this on a first date, Tom, you're suffocating me.'

'I've never felt like this on a first date, Tom, you're suffocating me.' mockup

'I've never felt like this on a first date, Tom, you're suffocating me.'

from $19.00

'Don't look now Muriel. But that Polyphemus guy has been giving you the eye all night.'

'Don't look now Muriel. But that Polyphemus guy has been giving you the eye all night.' mockup

'Don't look now Muriel. But that Polyphemus guy has been giving you the eye all night.'

from $19.00

Nailed him on the first date.

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..."

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.

from $19.00

Awkward First Dater Pillows Collection

Awkward First Dater Mugs

Explore our collection of mugs perfect for awkward first daters. Find humorous and supportive designs that brighten their day and bring smiles to their faces.

Awkward First Dater Prints

Browse our delightful prints that capture the humor of first dates. They make a perfect decoration to celebrate new beginnings with a smile.

Awkward First Dater T-Shirts

Discover witty and fun t-shirts crafted for the awkward first dater. Great for easing nerves and adding a humorous touch to their first dating experience.