Comedian And Father Of Four Shares Funny Conversations Between His Daughters

By Ruby M

Most of us know at least one dad who thinks that he has the best, most relatable sense of humor out there. And we let these dads continue thinking that they’re so funny because disheartening them by not laughing at their terrible jokes only means we have less chance of getting that Xbox we wanted for Christmas. This dad, however, is considered to actually be funny by his millions of followers on Twitter. But he isn’t the only one that can take credit for his comedy — a lot of his material comes from the humor of his four daughters and their shared conversations. If you have kids, or even if you don’t, get ready for a list of hilarious chats between a dad, his wife, and their sassy daughters.

A+ for Sass

There’s nothing quite as dreaded by an 8-year-old (except for maybe the monster hiding in the closet and the night light running out of batteries) than homework. And, some assignments are worse than others, like having to write an entire paragraph of words!

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Luckily for these kids, their dad is a famous comedian and writer, and he can probably help them knock that paragraph out in under an hour. But according to this 8-year-old, it has to actually be good, so dad can’t help. We aren’t sure if her writing is any good, but she should definitely get an A+ for sass.

I Won’t Say I’m in Love

Well, this kid has the right idea — we bet she’ll be a real heartbreaker someday. She doesn’t want to fall in love because that means distraction. And when you have things to do, you need to put all your focus into yourself. There’s no time for romance.

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She’ll likely grow up to be a career-driven, hard worker. But love always finds a way to come into your life when you least expect it — even if you don’t plan on it. But falling in love doesn’t mean that the rest of your dreams have to be put on standby. You can have it all!

When I Grow Up…

Any parent — especially of multiple mischievous siblings — can relate to the heart-stopping moments that take place when they hear one playful child tell the other to hold still because they “know what they’re doing.” They certainly do not know what they’re doing!

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If the parent doesn’t intervene and stop whatever it is they’re doing quickly enough, chances are there will be chaos. Be it an eruption of laughter, tears, or both, from the bald patch, attempted piercing, or as James stated — presumably amateur surgery.

Oh, How We Miss the Tooth Fairy

They say that youth is wasted on the young, and my, my, how that is true. Oh, how we miss the days of waiting for the tooth fairy to pay us her dues and not having the tiresome duties of paying bills, going to work, and keeping up a household full of kids.

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We wonder if Daddy dearest has told these kiddies that they best be ready to start earning their pocket money through chores when they run out of baby teeth to give, because the tooth fairy isn’t going to be around forever.

Freedom at Last

One thing this kid can say about being the youngest of four — you sure do get bullied and bossed around a lot. You’re the youngest, and the older siblings constantly remind you of that fact. They’re older, so you have to do what they say. 

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You’re little, so you can’t play with the older kids’ toys. You’re the youngest, so you have to have your turn in Monopoly last. At least at school, you’re all the same age and no one can tell daddy on you.

Just 5 more minutes

The morning rush to get to school in time is always more stressful for parents than it is for kids — especially when you’re a father of 4 mischievous little girls who love nothing more than to sleep in as much as they can.

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Naturally, James probably has to wake his kids up at least two times each and fight them to get up and get ready for school. They won’t get up on their own even with an alarm — they will simply just turn it off.

It Has Pocketssssss

Sorry James, but there are some things that, as a dad, you’re just not going to get. Take, for example, the fact that only girls would understand the power that comes with wearing a dress with pockets. Your 9-year-old is right. She is unstoppable.

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A dress with pockets means endless possibilities. It means no need for a handbag because our cherry lip balm can just be slid into our pocket, and that means free hands for getting up to all sorts of wayward things.

Sometimes, It’s OK to Give In

A determined child will often do whatever it takes to get their way, and when you’re a father of four smart-mouthed daughters, you’ve likely got your hands full with daily requests for fun activities and toys. With so many requests, they need to be clever in how they ask.

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Luckily for these girls — or more likely fortunate for dad — they didn’t have to try too hard to convince their father that a trip to the park would be just splendid. Just one Yoda quote was enough to convince dad that it was time to head out.

Who Really Has it Together?

We are so glad that every time this 9-year-old and her father have a conversation, it is documented on James’ Twitter page because this kid is gold and she should definitely consider following in her father’s comedic footsteps one day.

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How on earth are you to fool God, James, when even your 9-year-old kid knows it’s a lie? Of course, we’re just kidding around, but his daughter’s comeback to him, saying that dressing up for church is to show God that they have their act together, is simply priceless.

Spidey Revenge

Great thinking, little girl — don’t let your daddy kill the spider. Not because it’s cruel and the spider didn’t do anything wrong, but because if that spider’s family is anything like John Wick, then they will certainly be seeking vengeance. 

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Luckily for this family, they have a super-smart 7-year-old looking out for them. She’s always thinking two moves ahead of everybody else to make sure that everybody in her family is safe from harm — even from harmless arachnids, apparently.

I’d Like to Place an Order for a New Mom Please

One quiet Saturday afternoon found James and his 7-year-old at the park where a kitty stole their hearts. After a while of petting it, his daughter naturally asked if they could take it home — knowing full well that mom is allergic. 

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Of course, dad said no because of the allergy, so it’s only just for the 7-year-old who developed a newly formed attachment to said kitty and asked for a new mom instead. Funny? Yes. Possible? Absolutely not. Hopefully mom wasn’t too offended by this suggestion.

The Best Financial Planner

If only there was an easier way to get rid of bills rather than actually paying them. Oh wait, this kid has cleverly pointed out that if dad simply throws the bills away, he won’t have to worry about paying them anymore.

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Thanks to her expertise on the matter, dad has promoted her to the role of his financial planner — and any bills that pass the threshold of the front door now go straight to the bin. Anyone that comes to collect will have to take it up with the smartest 7-year-old in the room!

Dark Humor

Not every moment with this sassy family involves hilarious moments between James and one of his daughters. Sometimes, there are some rather ominous moments, too. Take this statement by his 8-year-old, for example. This observation is packed with dark humor.

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Most things will, in fact, shrivel up and die — especially if you stab them. Maybe if you’re having a Dawn of the Dead-themed Halloween, then carving the pumpkins a little early in the year will help with the vibe.

Keep Trying

A thrilling yet scary realization is that your child might be just as nutty as you. In this case, James is both inspired and terrified that his 7-year-old made a very dark yet surprisingly true comment: anything is breakable if you try hard enough.

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So, of course, if you try hard enough, any ornament (or daddy’s spirit) is breakable. And if you’re a child of four, that means it’s easy to blame one of your siblings for the damage. The odds are in your favor.

All’s Fair in Love and War

We’re not sure that the intended moral of the story of the beloved Disney classic Mulan is to go to war instead of getting married, but we’re not going to break this little girl’s spirit. And neither is her father. 

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The tale is about honor and sacrifice, but also about being true to yourself — something that the 2016 Blogger Dad of the Year inspires in his children every day with his hilarious and award-winning writing and celebrated social media presence.

Big Mood

With the bittersweet knowledge of the world available at children’s fingertips through social media, news, television, and the easy accessibility of the internet, a vague “I’m done” statement from a young girl is not uncommon these days. Just ask James…

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It’s also quite common for you, as a parent, to relate to these feelings of being “done” or “over it” — especially when you have the glamorous life of an adult where the world at large is constantly being shoved into your face.

I Have So Much to do I Could Die

If you’re a Sims fan, you know all about how this game works. If you’re not, then aside from us very subjectively stating that you should give the game a go, all you need to know is that it’s a simulation game. The “objective” is to navigate your Sim through daily life.

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This Sim was told to do several tasks and chores by the daughter playing the game, and instead of doing them, he just laid down and died. This must have been hilarious to experience, and if that’s not relatable, we don’t know what is.

Some Girls Just Want to Watch the World Burn

It’s always a little heartwarming when your kids start getting older and begin planning what they want to be when they grow up. They say things like “Doctor” or “Detective” or, in this case, “Firefighter.” But we doubt James expected the follow-up question.

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Imagine your daughter asking you if girls can be firefighters, to which you respond, “of course, girls can be whatever they want to be.” The follow-up to that is your kid asking if girls can be “fire-starters.” Yup, she just wants to watch the world burn.

Dobby is a Free Elf

This kid is definitely a Harry Potter fan and has taken advantage of the concept of freeing elves from the series, and has tricked her dad into handing her the very same dirty socks that he told her to put into the hamper.

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James’ daughter believes that she is now free from being told to do any chores by her dad because he gave her a piece of clothing. Unfortunately for her, this isn’t Harry Potter, and she isn’t an elf, so she’ll still be subject to doing chores and cleaning up after herself.

Why of Course There Were Dragons in the ’80s!

Somehow, it’s still hard to believe that we’re living in the 2020s. And, weirder still, the 2000s feel like give years ago, and the 1980s feel like 50 years ago. Nowadays being alive in the ’80s means you are, at the youngest, in your thirties, which is pretty old compared to a 5-year-old.

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In fact, to a 5-year-old the ’80s and the medieval times are one and the same in terms of how long ago they were. So it is only natural to wonder if dad was alive. And if he was, then it’s only proper to ask if there were any dragons all that time ago.

The Sass!

This is something that always happens when you have more than one child. No matter what you do, they fight. And what does any responsible parent do? They try to stop the debacle and get to the bottom of the issue to find a resolution.

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Part of coming to a resolution includes trying to determine who started the fight and who is the “victim.” In this case, one sassy child stated that it was James who was apparently in the wrong for having so many kids.

Just Don’t Go Back to Work

Something that we’ve learned about these kids from going through this list is that sleep, ice cream, and playful activities are what they live for. The bane of their existence is chores, work, and anything remotely dull or related to being an adult.

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For example, the mounds of work that mom brings home from work have got to go. It’s simple, mom just needs to stay home and not go back to work — that way, she won’t get any more boring work to do. It’s ingenious!

A Mighty Librarian

We’ve already covered what the 8-year-old wants to be when she grows up (a fire-starter for those of you who skipped that number on the list) and now we’re getting down to the other three. Next up is our sassy 5-year-old.

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She’s decided to become not one but two things — a warrior and a librarian. That way, she can whip anyone into shape who doesn’t respect the books in her library and maintain a strict “no tardiness” policy on returning books.

The Song of Our Time

Songwriting is but one of the many talents that James Breakwell’s youngest is a natural with. Along with keeping up the family sass, this little girl has written the next greatest hit song of our time. We’re sure that they’ll be playing it on the radio for years to come!

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The song is actually quite simple. The only lyrics are “everything’s a mess and I don’t care.” If that doesn’t wholly encapsulate at least the last decade of humanity, then we don’t know what does. We can’t wait to see what songs she comes up with next!

Runaway Reptiles

It’s always daunting when your daughter asks you a question, and you know it’s because they’ve done something that they weren’t supposed to do. In this case, it’s letting what we can only hope is the pet corn snake out of its cage.

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Or perhaps the real concern is that there isn’t a pet corn snake at all. Which begs the question: why did she start thinking about snakes and their ability to climb stairs — and where is the snake in question?!

Well Played

One day a year has been dubbed the day that all dads get treated like kings — Father’s Day. On this day, dads are gifted with breakfast in bed, and if they’re lucky enough, even a T-shirt or mug that reads “World’s Best Dad.” And if the gift is from a young child, you’ll likely be paying for it.

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The best dad deserves the best gift for Father’s Day. What dad would refuse to go to the store, buy the gift for himself, bring it home, and, naturally, share that gift — ice cream — with his loving kids? Well played!

Internet People

Dad wants some peace and quiet so that he can work on his audiobook that he insists people want to listen to. And his daughter, instead of noting his request, had a witty response to him — as per usual.

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Famous writers like Stephen King and Terry Pratchett have millions, if not billions, of fans. Most of the interactions with these fans are online, making them “internet people.” But that doesn’t mean that they’re not real, right? According to his eldest, it doesn’t. Ouch.

Muggles Just Don’t Get It

Most fun parents will introduce their children to the magical world of Harry Potter from a very young age, and most children under the age of 11 will daydream about that one day when they receive their Hogwarts letters via a friendly owl.

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So it’s really no surprise that James’ 7-year-old decided that she wanted to wear the invisibility cloak to school so that she can sneak around unseen by peers and teachers. Her dad simply doesn’t get it because he’s a muggle (non-magic folk).

Good Morning

No one wants to wake up in the early hours of the morning just to have to get dressed and go through the dreaded and dull halls of school, sit in boring classes, and do PE when they could be sleeping instead.

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Apparently, in this household, waking up is an option, and the choice available is to pass on that. We don’t think it’s going to hold up in the kitchen court, though, and someone clearly forgot to give dad the memo.

Too Many Cupcakes

As a kid, our parents told us that we couldn’t have a third helping of pudding, and that two was already too many. We wished we were grown-ups so we could be in charge and could eat an entire batch of cookies on our own.

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Then we grew up, binged on all the food we wanted because no one could tell us not to, and regretted the belly ache that undoubtedly followed. James knows how we feel, especially after eating 34 cupcakes! Was it worth it? Probably.

It’s Okay to Give In Sometimes

Sometimes it is too exhausting to tell your child “no” because you know that it doesn’t just end at “no.” You say “no,” they ask “why,” and you explain your reason, but that’s still not good enough because they have (in James’ case especially) some snarky response.

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So sometimes you just give in and say “yes” to ordering pizza or staying up an extra 30 minutes before bedtime because, after the day you’ve had at work, it’s just easier. Hopefully, your kids won’t try their luck like James’ eldest and catch onto the fact that you’re weak right now.

Rule-makers, not breakers

This conversation between James and his wife is likely one most couples have had after putting their kids to bed and finally having a moment to themselves before one or all of them find their way to their parents’ bed in the middle of the night.

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One weekend of sending the kids to their grandparents or friends so that you can have some much-needed alone time with your SO should be easy, right? After all, you’re the grown-ups; you make the rules. (We’re crying, too, James.)

Big Sister, Little Sister

Speaking of too many kids, the shock of seeing your youngest wearing a shirt that says “big sister” is a pretty ominous sign — unless, of course, he was hoping for kiddy number 5, which we doubt based on his initial shock.

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James left out the “*breathes sigh of relief*” at the end of this post. But we know he was probably pretty relieved to discover that, for now, there are only four chaotic beings rocking his world. Five if you include his wife.


When you’re walking through the park on a sunny Saturday morning with the family and your child asks to pet somebody’s dog, it’s the perfect opportunity to teach her some manners. There are certain unwritten rules of society, so you need to use every opportunity available to share your wisdom.

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This isn’t just any kid, though. This is James Breakwell’s sassy daughter, who we can only hope is more polite with strangers, whose response to having to ask the owner of the dog permission is unsurprisingly hilarious but also rather cheeky.

Ice Cream

There is a distinct difference between “need” and “want.” But when it comes to the creamy goodness of ice cream or anything else candy or dessert-related, is there really a difference between want and need? We don’t think so, and neither does James’ daughter.

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Food goes to the stomach, but dessert goes to the heart, and how can your heart be sweet without ice cream? So technically, the kid is right. Ice cream is a need, and you don’t need a reason for having it.

Queen President of the World

When you’re only 7-years-old, you have your whole life ahead of you. Fate hasn’t yet told you if you’re going to be popular, a cheerleader, head girl, or captain of the hockey ball team. You likely still think that boys have cooties.

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You still have big dreams like becoming the queen of the world or president of the United States (even if you’re not American), and who’s to stop you from dreaming of becoming both? Dream big, kids. You can be anything you want to be.

Potatoes, Potatoes

If dragons were around in the ’80s, it isn’t a stretch to believe that there was no other food aside from potatoes then, too. Did people even know what a burger was in the ’80s? Did ketchup and mayo even exist?

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These are the thoughts that go through a playful child’s mind as they ponder about their parent’s childhood. What was life like back then? How did they survive without Twitter and delicious meals that do not include anything as boring as mashed potatoes?

Brain Freeze

Sometimes your kids will ask you questions that you might not have the perfect answer to. After all, how can you explain to a child what it’s like to have a child? It can get a little complicated, and you don’t want that.

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This is a great explanation for any parent to give their child when they ask you what it’s like to have kids. It’s honest yet still reassures your little one(s) that they are the best thing in their parent’s lives — even if it does cause headaches.

Dad Just Wouldn’t Understand

Why is it that, when we’re 9-years-old, we feel like we know everything there is to know in the world, but when we’re 29, we don’t know anything at all? For example, when you’re nine and your dad is an English major…

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An English major can’t help you with grade school math. He’s only got room in his head for big fancy words that you don’t know the meaning of. But when you’re 9, you’re not going to admit that…unless you’re James’ daughter.

Boys Need Makeup Too

All the girls get to do their hair and makeup for big events like a wedding, and the boys just need to slick their hair back with some wax and sling on a belt and some shiny shoes, and Bob’s your uncle. They’re photo ready. 

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James told his kids that he’s pretty enough without makeup, but his daughters don’t seem to think so. Poor guy doesn’t seem to ever catch a break from his four snarky girls, not even for a happy occasion, like a wedding.

Bathroom Break

Sometimes when things get boring — like in the middle of a double period of Math or during the Priest’s long and repetitive sermon about something far beyond a 7-year-old’s cares — it is time to pull the good old “need to potty” trick.

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It’s simple — whenever you’re somewhere that you don’t want to be, just tell your dad that you need to pee. Then all you have to do is take a really long time in the bathroom, and hopefully, whatever was boring will be over by the time your dad comes looking for you.

Always Right, Never Wrong

Most kids follow the mantra “I’m always right and never wrong.” And if you have more than one kid, you know all about the dramatic arguments between siblings — especially when everybody thinks that they’re right. James has had to deal with his fair share of these squabbles.

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When James caught his daughters fighting — as kids do — he told them to stop arguing, and, of course, these kids didn’t just do what they were told. According to his eldest, she wasn’t arguing — she was simply being right.

The Youngest Member of the FBI

It’s no surprise that when little ones play, they take on characters like doctors, spies, and famous people. In the case of James’ kid, she was a member of the FBI whose been tasked with training the newbies on how to defuse a bomb.

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The popular writer must be so proud of his 5-year-old, all grown up and saving the day. He’s right — he should probably pay attention so that he can teach us and everyone on Twitter how to defuse a bomb.

Four is Enough!

At first, maybe James and his wife thought that their eldest was being sweet, asking her loving parents if more sisters would be on the way — or maybe a brother — so that she could have more siblings to love and play with.

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Oh, how they were wrong. It’s no surprise, though, that this sassy kid (being the first born) was one to state quite blatantly the fact that her parents could have simply stopped at one kid — making her their one and only treasure.

Dogs Can’t See Colors

This one is a pretty sad statement because if anybody knows how happy dogs get over, well, anything exciting, then they can imagine how many tail wags a rainbow would give a doggo. If only they could see all the colors. 

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But alas, doggos can’t see colors, which is why in the movies like Cats and Dogs it’s always the cat who cuts the wires on the bomb or notices the big red button that dogs simply cannot see. Thanks, James, now we’re also sad.