Child Reaching Trouble Milestone Gifts

Looking for a gift for your child's reaching a tricky milestone? Our collection offers humorous and heartfelt products that celebrate those “kid moments” with style and humor. Perfect for parents and families wanting to remember these special times.

Child Reaching Milestones Child's Milestone Child Milestone Child's Musical Milestone Child's Artistic Milestone Child's First Milestone Child's Milestones Child's Speech Milestone Celebrating Child's Milestone Teen Troublemaker

All Products Prints T-Shirts Mugs Pillows

'I'm afraid releasing that information would not be in the public interest.'

'I'm afraid releasing that information would not be in the public interest.' mockup

'I'm afraid releasing that information would not be in the public interest.' mockup

'I'm afraid releasing that information would not be in the public interest.' mockup

'I'm afraid releasing that information would not be in the public interest.' mockup

'I'm afraid releasing that information would not be in the public interest.'

from $19.00

Randall couldn't wait to see what else the 'Magic Trash Can' could make disappear.

Randall couldn't wait to see what else the 'Magic Trash Can' could make disappear. mockup

Randall couldn't wait to see what else the 'Magic Trash Can' could make disappear. mockup

Randall couldn't wait to see what else the 'Magic Trash Can' could make disappear. mockup

Randall couldn't wait to see what else the 'Magic Trash Can' could make disappear. mockup

Randall couldn't wait to see what else the 'Magic Trash Can' could make disappear.

from $19.00

'Sire, your new fortress was fine for your nephew's fifth, but I fear it is set for a sterner test.'

'Sire, your new fortress was fine for your nephew's fifth, but I fear it is set for a sterner test.' mockup

'Sire, your new fortress was fine for your nephew's fifth, but I fear it is set for a sterner test.' mockup

'Sire, your new fortress was fine for your nephew's fifth, but I fear it is set for a sterner test.' mockup

'Sire, your new fortress was fine for your nephew's fifth, but I fear it is set for a sterner test.' mockup

'Sire, your new fortress was fine for your nephew's fifth, but I fear it is set for a sterner test.'

from $19.00

When a toddler hands you their ringing toy phone, you answer it!

When a toddler hands you their ringing toy phone, you answer it! mockup

When a toddler hands you their ringing toy phone, you answer it! mockup

When a toddler hands you their ringing toy phone, you answer it! mockup

When a toddler hands you their ringing toy phone, you answer it! mockup

When a toddler hands you their ringing toy phone, you answer it!

from $19.00

Child laughs while making farting sound under arm. Dad says, 'Isn't it nice when they find something they're good at?

Child laughs while making farting sound under arm. Dad says, 'Isn't it nice when they find something they're good at? mockup

Child laughs while making farting sound under arm. Dad says, 'Isn't it nice when they find something they're good at? mockup

Child laughs while making farting sound under arm. Dad says, 'Isn't it nice when they find something they're good at? mockup

Child laughs while making farting sound under arm. Dad says, 'Isn't it nice when they find something they're good at? mockup

Child laughs while making farting sound under arm. Dad says, 'Isn't it nice when they find something they're good at?

from $19.00

'Oh Darling, you must be so proud: Your first wart!'

'Oh Darling, you must be so proud: Your first wart!' mockup

'Oh Darling, you must be so proud: Your first wart!' mockup

'Oh Darling, you must be so proud: Your first wart!' mockup

'Oh Darling, you must be so proud: Your first wart!' mockup

'Oh Darling, you must be so proud: Your first wart!'

from $19.00

'At lone at last.'

'At lone at last.' mockup

'At lone at last.' mockup

'At lone at last.' mockup

'At lone at last.' mockup

'At lone at last.'

from $19.00

"Here's the baby's first birthday, her second, her third, look at her gifts..."

"Here's the baby's first birthday, her second, her third, look at her gifts..." mockup

"Here's the baby's first birthday, her second, her third, look at her gifts..." mockup

"Here's the baby's first birthday, her second, her third, look at her gifts..." mockup

"Here's the baby's first birthday, her second, her third, look at her gifts..." mockup

"Here's the baby's first birthday, her second, her third, look at her gifts..."

from $19.00

"We tried 'Baby Mozart,' but he prefers 'Baby John Cage.'"

"We tried 'Baby Mozart,' but he prefers 'Baby John Cage.'" mockup

"We tried 'Baby Mozart,' but he prefers 'Baby John Cage.'" mockup

"We tried 'Baby Mozart,' but he prefers 'Baby John Cage.'" mockup

"We tried 'Baby Mozart,' but he prefers 'Baby John Cage.'" mockup

"We tried 'Baby Mozart,' but he prefers 'Baby John Cage.'"

from $19.00

'It was the little darling's first time sitting up at the dining table!'

'It was the little darling's first time sitting up at the dining table!' mockup

'It was the little darling's first time sitting up at the dining table!' mockup

'It was the little darling's first time sitting up at the dining table!' mockup

'It was the little darling's first time sitting up at the dining table!' mockup

'It was the little darling's first time sitting up at the dining table!'

from $19.00

'Baby's first two-step.'

'Baby's first two-step.' mockup

'Baby's first two-step.' mockup

'Baby's first two-step.' mockup

'Baby's first two-step.' mockup

'Baby's first two-step.'

from $19.00

'What's the best kind of glue to fix a TV screen?'

'What's the best kind of glue to fix a TV screen?' mockup

'What's the best kind of glue to fix a TV screen?' mockup

'What's the best kind of glue to fix a TV screen?' mockup

'What's the best kind of glue to fix a TV screen?' mockup

'What's the best kind of glue to fix a TV screen?'

from $19.00

"You're writing a memoir? You're seven years old. Do you honestly think you can capture the interest of readers with such a short—wait, is that my name?!"

"You're writing a memoir? You're seven years old. Do you honestly think you can capture the interest of readers with such a short—wait, is that my name?!" mockup

"You're writing a memoir? You're seven years old. Do you honestly think you can capture the interest of readers with such a short—wait, is that my name?!" mockup

"You're writing a memoir? You're seven years old. Do you honestly think you can capture the interest of readers with such a short—wait, is that my name?!" mockup

"You're writing a memoir? You're seven years old. Do you honestly think you can capture the interest of readers with such a short—wait, is that my name?!" mockup

"You're writing a memoir? You're seven years old. Do you honestly think you can capture the interest of readers with such a short—wait, is that my name?!"

from $19.00

"As it's your birthday, would you like to go in the Big Chair?"

"As it's your birthday, would you like to go in the Big Chair?" mockup

"As it's your birthday, would you like to go in the Big Chair?" mockup

"As it's your birthday, would you like to go in the Big Chair?" mockup

"As it's your birthday, would you like to go in the Big Chair?" mockup

"As it's your birthday, would you like to go in the Big Chair?"

from $19.00

"Wait! I don't want to be disease resistant!"

"Wait! I don't want to be disease resistant!" mockup

"Wait! I don't want to be disease resistant!" mockup

"Wait! I don't want to be disease resistant!" mockup

"Wait! I don't want to be disease resistant!" mockup

"Wait! I don't want to be disease resistant!"

from $19.00

"We're hoping that someday Rosalie will be a major player in the creative economy."

"We're hoping that someday Rosalie will be a major player in the creative economy." mockup

"We're hoping that someday Rosalie will be a major player in the creative economy." mockup

"We're hoping that someday Rosalie will be a major player in the creative economy." mockup

"We're hoping that someday Rosalie will be a major player in the creative economy." mockup

"We're hoping that someday Rosalie will be a major player in the creative economy."

from $19.00

"Charles, look! He’s sending his first text!"

"Charles, look! He’s sending his first text!" mockup

"Charles, look! He’s sending his first text!" mockup

"Charles, look! He’s sending his first text!" mockup

"Charles, look! He’s sending his first text!" mockup

"Charles, look! He’s sending his first text!"

from $19.00

'The man was real nice about it. He gave me my ball back and even said you can expect a nice call from his lawyer.'

'The man was real nice about it. He gave me my ball back and even said you can expect a nice call from his lawyer.' mockup

'The man was real nice about it. He gave me my ball back and even said you can expect a nice call from his lawyer.' mockup

'The man was real nice about it. He gave me my ball back and even said you can expect a nice call from his lawyer.' mockup

'The man was real nice about it. He gave me my ball back and even said you can expect a nice call from his lawyer.' mockup

'The man was real nice about it. He gave me my ball back and even said you can expect a nice call from his lawyer.'

from $19.00

Sparkler mockup

Sparkler mockup

Sparkler mockup

Sparkler mockup

Sparkler

from $19.00

Eagle parenting.

Eagle parenting. mockup

Eagle parenting. mockup

Eagle parenting. mockup

Eagle parenting. mockup

Eagle parenting.

from $19.00

"Wait, so his first whole sentence was 'I don't want to work, I just want to bang on the drum all day'?!"

"Wait, so his first whole sentence was 'I don't want to work, I just want to bang on the drum all day'?!" mockup

"Wait, so his first whole sentence was 'I don't want to work, I just want to bang on the drum all day'?!" mockup

"Wait, so his first whole sentence was 'I don't want to work, I just want to bang on the drum all day'?!" mockup

"Wait, so his first whole sentence was 'I don't want to work, I just want to bang on the drum all day'?!" mockup

"Wait, so his first whole sentence was 'I don't want to work, I just want to bang on the drum all day'?!"

from $19.00

Dominant hand reveal party

Dominant hand reveal party mockup

Dominant hand reveal party mockup

Dominant hand reveal party mockup

Dominant hand reveal party mockup

Dominant hand reveal party

from $19.00

'His next appointment is on the 17th when the clock's little hand is on the two and the big one's on the nine.'

'His next appointment is on the 17th when the clock's little hand is on the two and the big one's on the nine.' mockup

'His next appointment is on the 17th when the clock's little hand is on the two and the big one's on the nine.' mockup

'His next appointment is on the 17th when the clock's little hand is on the two and the big one's on the nine.' mockup

'His next appointment is on the 17th when the clock's little hand is on the two and the big one's on the nine.' mockup

'His next appointment is on the 17th when the clock's little hand is on the two and the big one's on the nine.'

from $19.00

'Jimmy made his first blog post today.'

'Jimmy made his first blog post today.' mockup

'Jimmy made his first blog post today.' mockup

'Jimmy made his first blog post today.' mockup

'Jimmy made his first blog post today.' mockup

'Jimmy made his first blog post today.'

from $19.00

They were American tourists, visiting gay Paree...and yet this was a Mexican stand off??

They were American tourists, visiting gay Paree...and yet this was a Mexican stand off?? mockup

They were American tourists, visiting gay Paree...and yet this was a Mexican stand off?? mockup

They were American tourists, visiting gay Paree...and yet this was a Mexican stand off?? mockup

They were American tourists, visiting gay Paree...and yet this was a Mexican stand off?? mockup

They were American tourists, visiting gay Paree...and yet this was a Mexican stand off??

from $19.00

"They're secret service. They appeared the day Billy decided he wanted to be president when he grew up."

"They're secret service. They appeared the day Billy decided he wanted to be president when he grew up." mockup

"They're secret service. They appeared the day Billy decided he wanted to be president when he grew up." mockup

"They're secret service. They appeared the day Billy decided he wanted to be president when he grew up." mockup

"They're secret service. They appeared the day Billy decided he wanted to be president when he grew up." mockup

"They're secret service. They appeared the day Billy decided he wanted to be president when he grew up."

from $19.00

"I'm too old for baby limas."

"I'm too old for baby limas." mockup

"I'm too old for baby limas." mockup

"I'm too old for baby limas." mockup

"I'm too old for baby limas." mockup

"I'm too old for baby limas."

from $19.00

'I bronzed his first pair of running shoes.'

'I bronzed his first pair of running shoes.' mockup

'I bronzed his first pair of running shoes.' mockup

'I bronzed his first pair of running shoes.' mockup

'I bronzed his first pair of running shoes.' mockup

'I bronzed his first pair of running shoes.'

from $19.00

"Honey, your head's through the armhole again."

"Honey, your head's through the armhole again." mockup

"Honey, your head's through the armhole again." mockup

"Honey, your head's through the armhole again." mockup

"Honey, your head's through the armhole again." mockup

"Honey, your head's through the armhole again."

from $19.00

'My grandson has been walking from an early age. . . Oh yes, in fact, by the time he was two he'd been walking three years.'

'My grandson has been walking from an early age. . . Oh yes, in fact, by the time he was two he'd been walking three years.' mockup

'My grandson has been walking from an early age. . . Oh yes, in fact, by the time he was two he'd been walking three years.' mockup

'My grandson has been walking from an early age. . . Oh yes, in fact, by the time he was two he'd been walking three years.' mockup

'My grandson has been walking from an early age. . . Oh yes, in fact, by the time he was two he'd been walking three years.' mockup

'My grandson has been walking from an early age. . . Oh yes, in fact, by the time he was two he'd been walking three years.'

from $19.00

Girl asking her little cousin what he would like for his birthday

Girl asking her little cousin what he would like for his birthday mockup

Girl asking her little cousin what he would like for his birthday mockup

Girl asking her little cousin what he would like for his birthday mockup

Girl asking her little cousin what he would like for his birthday mockup

Girl asking her little cousin what he would like for his birthday

from $19.00

Child Reaching Trouble Milestone Gifts Collection

Child Reaching Trouble Milestone Mugs

Explore our mugs collection that celebrates your child's milestone adventures—perfect for morning coffee and daily laughs.

Child Reaching Trouble Milestone Pillows

Check out our cozy pillows that showcase your child's milestone moments—bring humor and comfort to your home.

Child Reaching Trouble Milestone Prints

Browse our printable art that captures the humor and heart of childhood milestones—ideal for framing and special keepsakes.

Child Reaching Trouble Milestone T-Shirts

Discover our T-shirts featuring humorous takes on childhood milestones—funwear that celebrates growth and giggles.