At 37, I thought I could finally date in peace until my Mom crashed dinner with a list of rules… and somehow ended up on a date with my boyfriend.
I always knew I had a mom. But sometimes, it felt like my mom was my whole life. I was 37, but that didn’t stop her from asking me every single day:
“Are you wearing warm socks?” or “Are you sure he looked at you with respect and not… interest?”
For illustration purposes only | Source: Midjourney
I worked in a museum, adored art history, lived in my own apartment, had a bank account, and had two degrees… Yet every time I saw “Mom calling” on my phone, I instinctively straightened my posture.
She controlled everything. From when I should go to bed to what color I painted my nails.
Once, I ordered salmon delivery, and 20 minutes later, she called.
“I saw him go into your house. Was that him?”
For illustration purposes only | Source: Pexels
“Mom, are you spying on my house?”
“I just sat in the car nearby. In case of suspicious movement.”
She had binoculars. And a notebook. She called it “just in case.”
As a child, it was cute. At 20, it got annoying. By 30, I began to question our “normal.”
At 37, I met Theo.
For illustration purposes only | Source: Pexels
For the first time in my life, I didn’t tell her right away.
It was my first grown-up secret. And, of course, it lasted exactly three days. Until Mom ruined everything.
But I’ll tell you that in a moment.
For illustration purposes only | Source: Pexels
***
I was preparing for my dinner with Theo. I baked a pie I found online, not from Mom’s sacred recipe book.
Even if it came out a bit burnt and the chicken was a little dry — those were my mistakes. My life.
I could already imagine my mother’s face if she saw the meal — a guaranteed explosion. I smiled quietly to myself while checking the candles.
For illustration purposes only | Source: Midjourney
A week earlier, she declared, “I want to meet him. In person. At my house. At the table. With my questions.”
“Mom, let me be an adult for once. I’ll decide when to introduce you.”
She backed off for once. It felt odd, but I didn’t think much of it. Big mistake.
That night, Theo came over for the first time. He brought tulips, non-alcoholic wine (knowing I was tired after work), and a cake from the bakery I always visit during lunch.
For illustration purposes only | Source: Midjourney
“I just wanted to get everything right,” he smiled, setting the plates.
“Theo, with you, it always feels right.”
Something warm and calm bloomed in my chest. We talked for hours. Laughed. Dreamed.
“Imagine… a little house by an old lighthouse,” he said.
For illustration purposes only | Source: Midjourney
“And in the basement — an archive of old love letters.”
“You’d preserve them, and I’d write new ones.”
Candles were burning low. Music hummed softly. He touched my hand.
“I thought after all the heartbreaks, nothing would ever happen again. And then you came along…”
And at that exact moment…
For illustration purposes only | Source: Midjourney
“ACHOO!”
From the closet. We froze.
“You’re not alone?” Theo shot me a look.
I got up. Opened the closet.
For illustration purposes only | Source: Pexels
“Mooom?!”
She sat in the dark. With a headlamp. And a thermos.
“What… what are you doing?!”
“Oh, hi! I was just checking if you’re storing things in your closet without lavender,” she mumbled, not even trying to sound convincing.
For illustration purposes only | Source: Midjourney
“You broke into my apartment?!”
“I was just making sure. Listening. Evaluating. I didn’t interfere!”
Theo, somehow, still managed to smile politely.
“Good evening. I’m Theo. Very nice to meet you.”
For illustration purposes only | Source: Midjourney
“Theo. Short. Like most male patients,” Mom said, sitting on the couch. “Sit. Let’s get to know each other.”
I wanted to run. But Theo sat down. Bravely.
And the interrogation began.
“Do you have a job?”
“Yes. I teach literature…”
For illustration purposes only | Source: Midjourney
“Do you work 9 to 5?”
“Flexible hours.”
“So, no structure. Got it. Do you drink alcohol?”
“A glass of wine, sometimes…”
“Sometimes means regularly.”
For illustration purposes only | Source: Midjourney
“Mom…”
“Quiet, Eliza. I’m asking.”
Then she turned back to him again, “How many women before my daughter?”
“I… excuse me?”
“Are you deaf?”
For illustration purposes only | Source: Midjourney
“No, I just think that’s a bit…”
“You should always think. Before approaching a woman with serious intentions.”
Theo looked at me. As if to ask, “Is this a joke?”
I tried to say with my eyes, “No. This is my life.”
For illustration purposes only | Source: Midjourney
Mom stood up. “Now, a test.”
“What?” we both said.
“Wipe the table. With a sponge. No streaks. If there’s even one mark — you’re not for her.”
“Mom, enough!”
I was desperate and angry. But to my greatest surprise…
For illustration purposes only | Source: Midjourney
Theo stood up, went to the kitchen, found the sponge… and wiped. It was perfect. She checked the surface and ran her finger across.
“Hmm. Survived. For now.”
Then, Mom dramatically handed Theo a paper. He smiled while skimming it, then slowly, he frowned before handing it to me.
“I think I should go. I’ll call you.”
For illustration purposes only | Source: Midjourney
He left. Just like that. I finally looked down at the letters she wrote in thick black marker.
RULES FOR DATING MY DAUGTER
1. Have a job.
2. Understand I don’t like you.
3. I am EVERYWHERE.
4. You make HER cry — I make YOU cry.
5. Be home 30 min early.
6. SHE is my PRINCESS. Not your conquest.
7. I don’t mind going to jail.
For illustration purposes only | Source: Celebritist
Daugter. With a typo. That said it all.
“Mom, it’s time for you to go.”
“Oh, sweetie, if he leaves at the first sign of trouble, is he even a man?”
“He didn’t leave me. He said he’d call.”
“Same thing.”
For illustration purposes only | Source: Midjourney
“Maybe he just didn’t enjoy being around you?”
“You’re overreacting.”
“You crossed the line, Mom! Please, leave. I want to be alone.”
Mom’s words echoed in my head.
Has Theo really left… forever?
For illustration purposes only | Source: Midjourney
***
Three days passed. No texts. No calls. I caved and sent him a short message:
“I’m sorry for how everything went. You didn’t deserve that.”
Seen. No reply.
And then — a knock at the door. I opened it, my heart racing. It was him and he was there with flowers.
“Come on. I’ve planned a date… for you and your Mom.”
For illustration purposes only | Source: Pexels
I blinked. “What?”
“Just trust me.”
We picked up my Mom. She barely got in the car before starting her usual commentary.
“Where are we going? I have to defrost the freezer!”
“Surprise,” Theo smiled.
For illustration purposes only | Source: Midjourney
The first stop? His lecture.
Mom and I sat in the back. Theo stood in front of a class full of students, talking about love in literature.
“To be with someone doesn’t always feel poetic. But it’s always worth it.”
“Oh, I might fall asleep here,” Mom whispered.
“Mom. Shhh.”
For illustration purposes only | Source: Midjourney
“If he’s trying to seduce us both with lectures — he failed.”
I gave her a look. But I held on. I knew this wasn’t all Theo had planned.
Next stop — a boat ride. On the lake, with a plaid blanket, strawberries, and tea in a thermos. (Yes, the exact tea Mom liked. He remembered.)
For illustration purposes only | Source: Midjourney
“Yet another romantic coma,” Mom muttered, but this time, she was chuckling.
As we floated, Theo turned to her gently.
“So, Barbara. What are your hobbies?”
She raised an eyebrow.
“Hobbies? Suspicion. Avoiding scams. Crosswords when I can’t sleep.”
For illustration purposes only | Source: Pexels
“I bet you’re good at them.”
“I once found three typos in The New York Times. Sent them a letter. And you didn’t find one.”
“You planted that typo?”
“Of course, sweetie — it was a test for your Theo.”
For illustration purposes only | Source: Pexels
“A test? For spelling? Mom, he’s a university professor!”
“No, more like a test for politeness,” she smirked. “He passed.”
Then she leaned to move closer to the edge… and slipped.
SPLASH.
She fell right into the water. I gasped. Then, she laughed so hard I nearly joined her.
For illustration purposes only | Source: Midjourney
“YOU LAUGHING? I COULD DROWN!”
Theo jumped in without hesitation. Swam straight to her, helped her out, and wrapped her in a blanket. Soaked, shivering, furious — but secretly touched. Back on land, she was about to stomp away.
“I need to go home. I’m done.”
Theo calmly said, “There’s a sports store nearby. Time for a wardrobe refresh.”
For illustration purposes only | Source: Pexels
He disappeared. Came back ten minutes later with two matching athletic outfits. One for me. One for Mom. She held hers suspiciously.
“How did you guess my size?”
“Easy. You’re built perfectly for a Medium. Athletic and classic.”
She smiled. Barely. Quietly. But I saw it. She loved attention.
For illustration purposes only | Source: Midjourney
We changed. And then — the climbing wall.
“Last challenge, I promise,” Theo grinned. “Climbing wall. One climbs, the other keeps the rope. Trust exercise.”
“Oh no. I’m 60!”
“Exactly. Perfect age for adventure.”
For illustration purposes only | Source: Pexels
To my absolute shock, Mom went first. Halfway up, she shouted:
“THEO! IF I FALL — I’M HAUNTING YOU!”
She didn’t fall. She reached the top. And when she came down, her eyes were gleaming.
“Okay, professor. Not bad.”
For illustration purposes only | Source: Midjourney
“To end the day,” Theo said, “I’d like to make you both dinner. My place.”
Mom looked at me. “I have no choice. I need to see where this man lives. Maybe I’ll discover his secret lair.”
***
Theo’s house was beautiful. Clean. Warm. It smelled like citrus and cedar. I’d never been there before. And I was stunned.
For illustration purposes only | Source: Pexels
“Did you buy this on a teacher’s salary or rob a bank?” Mom asked, peeking into the kitchen.
“Started saving in high school. Plus I teach online courses on the side. Hard work pays off.”
“Well, look at you,” she muttered. Then, louder, “Does the fridge clean itself, or are you just this weird?”
Theo just laughed.
For illustration purposes only | Source: Midjourney
We sat on the terrace. Theo grilled steaks nearby while the sun dipped low. Mom leaned back. Actually relaxed.
“You know… he’s not so bad, honey.”
“Really? Wow. Mom, you’re on fire today.”
“I was too distrustful. Because your father left. And I didn’t want you to get burned like I did.”
For illustration purposes only | Source: Midjourney
“But Mom, it’s my life. I need to make my own mistakes. Walk my own path.”
“Theo is wonderful. It’s obvious he loves you. I mean, he jumped in a lake to save his future mother-in-law.”
We both laughed.
“And he could’ve dropped me on that climbing wall. But he didn’t. That’s some nerve control.”
Theo joined us, carrying two plates.
For illustration purposes only | Source: Midjourney
“Hungry?”
“Always,” Mom said.
“Even for this? Because I have one more course.”
Theo knelt on one knee.
“Eliza, these past three months have been the best of my life. You’ve brought color back into everything. And your mom… we’re friends now.”
For illustration purposes only | Source: Midjourney
“Almost,” Mom added.
“Not even the rule list could scare me away. I want to share my home, my life… all of it. And yes, even see your mom — but no more than twice a week.”
He laughed. I gasped.
“Will you marry me?”
For illustration purposes only | Source: Midjourney
I blinked. Heart racing.
“Sweetheart,” Mom nudged me. “I’d have said yes already.”
“YES. Of course — yes!”
For illustration purposes only | Source: Pexels
***
Mom changed.
She started Pilates, bought her first floral swimsuit, and we no longer lived in a co-dependent loop. We were separate but always family.
Finally, our coffee dates felt like chats between old friends.
For illustration purposes only | Source: Midjourney
She told me about her fitness class. I told her how Theo’d forgotten to take out the trash and called it a “creative delay.”
I finally became myself. And I think — she also did.
For illustration purposes only | Source: Midjourney
Tell us what you think about this story and share it with your
I Married a Homeless Man to Spite My Parents – A Month Later, I Came Home and Froze in Shock at What I Saw
When I offered to marry a homeless stranger, I thought I had it all figured out. It seemed like the perfect arrangement to please my parents with no strings attached. Little did I know I’d be shocked to walk into my house a month later.
I’m Miley, 34 years old, and this is the story of how I went from being a happily single career woman to marrying a homeless man, only to have my world turned upside down in the most unexpected way.
A woman in her bedroom | Source: Midjourney
My parents have been on my case about getting married for as long as I can remember. I feel like they have a timer ticking away in their heads, counting down the seconds until my hair starts turning white.
As a result, every family dinner turned into an impromptu matchmaking session.
“Miley, honey,” my mom, Martha, would start. “You remember the Johnsons’ son? He just got promoted to regional manager at his firm. Maybe you two should grab coffee sometime?”
A woman talking to her daughter | Source: Midjourney
“Mom, I’m not interested in dating right now,” I’d say. “I’m focused on my career.”
“But sweetheart,” my dad, Stephen, would chime in, “your career won’t keep you warm at night. Don’t you want someone to share your life with?”
“I share my life with you guys and my friends,” I’d counter. “That’s enough for me right now.”
But they wouldn’t let up. It was a constant barrage of “What about so-and-so?” and “Did you hear about this nice young man?”
One night, things took a turn for the worse.
A close-up shot of chairs in a house | Source: Pexels
We were having our usual Sunday dinner when my parents dropped a bombshell.
“Miley,” my dad said in a serious tone. “Your mother and I have been thinking.”
“Oh boy, here we go,” I mumbled.
“We’ve decided,” he continued, ignoring my sarcasm, “that unless you’re married by your 35th birthday, you won’t see a cent of our inheritance.”
“What?” I blurted out. “You can’t be serious!”
“We are,” my mom chimed in. “We’re not getting any younger, honey. We want to see you settled and happy. And we want grandchildren while we’re still young enough to enjoy them.”
A woman looking at her daughter | Source: Midjourney
“This is insane,” I sputtered. “You can’t blackmail me into getting married!”
“It’s not blackmail,” my dad insisted. “It’s, uh, it’s incentive.”
I stormed out of their house that night, unable to believe what just happened. They’d given me an ultimatum, implying that I needed to find a husband in a few months or kiss my inheritance goodbye.
I was angry, but not because I wanted the money. It was more about the principle of the thing. How dare they try to control my life like this?
A woman looking at her mother | Source: Midjourney
For weeks, I didn’t answer their calls or visit them. Then, one evening, I got an excellent idea.
I was walking home from work, thinking about spreadsheets and deadlines, when I spotted him. A man, probably in his late 30s, sat on the sidewalk with a cardboard sign asking for change.
He looked rough, had an unkempt beard, and wore dirty clothes, but there was something in his eyes. A kindness and a sadness that made me pause.
A homeless man | Source: Pexels
That’s when an idea struck me. It was crazy, but it felt like the perfect solution to all my problems.
“Excuse me,” I said to the man. “This might sound crazy, but, um, would you like to get married?”
The man’s eyes widened in shock. “I’m sorry, what?”
“Look, I know this is weird, but hear me out,” I said, taking a deep breath. “I need to get married ASAP. It would be a marriage of convenience. I’d provide you with a place to live, clean clothes, food, and some money. In return, you’d just have to pretend to be my husband. What do you say?”
He stared at me for what felt like an eternity. I was sure he thought I was kidding.
A close-up shot of a man’s face | Source: Midjourney
“Lady, are you for real?” he asked.
“Completely,” I assured him. “I’m Miley, by the way.”
“Stan,” he replied, still looking bewildered. “And you’re seriously offering to marry a homeless guy you just met?”
I nodded.
“I know it sounds insane, but I promise I’m not a serial killer or anything. Just a desperate woman with meddling parents.”
“Well, Miley, I gotta say, this is the strangest thing that’s ever happened to me.”
A homeless man sitting outdoors | Source: Pexels
“So, is that a yes?” I asked.
He looked at me for a long moment, and I saw that spark in his eyes again. “You know what? Why the hell not. You’ve got yourself a deal, future wife.”
And just like that, my life took a turn I never could have imagined.
I took Stan shopping for new clothes, got him cleaned up at a salon, and was pleasantly surprised to discover that underneath all that grime was a rather handsome man.
A man smiling | Source: Midjourney
Three days later, I introduced him to my parents as my secret fiancé. To say they were shocked would be an understatement.
“Miley!” my mom exclaimed. “Why didn’t you tell us?”
“Oh, you know, I wanted to make sure it was serious before I said anything,” I lied. “But Stan and I are so in love, aren’t we, honey?”
Stan, to his credit, played along beautifully. He charmed my parents with made-up stories of our whirlwind romance.
A month later, we were married.
A newly wed couple | Source: Pexels
I made sure to get a rock-solid prenup, just in case my little scheme backfired. But to my surprise, living with Stan wasn’t half bad.
He was funny, smart, and always ready to help around the house. We fell into an easy friendship, almost like roommates who occasionally had to pretend to be madly in love.
However, there was just one thing that nagged at me.
A woman looking straight ahead | Source: Midjourney
Whenever I asked Stan about his past, about how he ended up on the streets, he’d clam up. His eyes would cloud over, and he’d quickly change the subject. It was a mystery that both intrigued and frustrated me.
Then came the day that changed everything.
It was a regular day when I returned home from work. As I entered the house, a trail of rose petals caught my attention. It led me into the living room.
A woman’s hand on a doorknob | Source: Midjourney
The sight that greeted me in the living room left me speechless. The entire room was filled with roses, and a huge heart made of petals was on the floor.
And there, in the center of it all, stood Stan.
But this wasn’t the Stan I knew. Gone were the comfortable jeans and T-shirts I gave him.
Instead, he was dressed in a sleek black tuxedo that looked like it cost more than my monthly rent. And in his hand, he held a small velvet box.
A man standing in a living room | Source: Midjourney
“Stan?” I managed to squeak out. “What’s going on?”
He smiled, and I swear my heart skipped a beat.
“Miley,” he said. “I wanted to thank you for accepting me. You’ve made me incredibly happy. I would be even happier if you truly loved me and became my wife, not just in name but in real life. I fell in love with you the moment I saw you, and this past month we’ve spent together has been the happiest of my life. Will you marry me? For real this time?”
A man talking to his wife | Source: Midjourney
I stood there with eyes wide open, struggling to process what was happening. A thousand questions raced through my mind, but one pushed its way to the front.
“Stan,” I said slowly, “where did you get the money for all this? The tuxedo, the flowers, and that ring?”
“I guess it’s time I told you the truth,” he said before taking a deep breath. “You see, I never told you how I became homeless because it was too complicated, and it could have put you in a difficult position. And I loved our life together so much.”
A man talking to his wife in the living room | Source: Midjourney
“I became homeless because my brothers decided to get rid of me and take over my company,” he continued. “They forged documents, faked my signatures, and even stole my identity. One day, they dropped me off in this town, miles away from home. When I tried going to the police, they pulled strings, and I never got any help. They even bribed my lawyer.”
I quietly listened as Stan poured out his story.
A woman looking at her husband | Source: Midjourney
How he’d lost everything, how he’d spent months just trying to survive on the streets. And then, how meeting me had given him the push he needed to fight back.
“When you gave me a home, clean clothes, and a little money, I decided to fight back,” he explained. “I contacted the best law firm in the country, one that my brothers couldn’t influence because it works for their competitors.”
A man talking on the phone | Source: Pexels
“I told them my story and promised them a substantial payout,” he revealed. “At first, they didn’t want to take the case without an advance, but when they realized they could finally outsmart their rivals, they agreed. Thanks to them, a court case is set for next month, and my documents and bank accounts have been restored.”
He paused, looking at me with those kind eyes that had first caught my attention.
A man looking straight ahead | Source: Midjourney
“I’ll be honest with you,” he smiled. “I’m not a poor man. I’ve spent my whole life looking for love, but every woman I met was only interested in my money. You, however, were kind to me when you thought I had nothing. That’s why I fell for you. I’m sorry I kept all this from you for so long.”
I sank onto the couch, unable to process his story. I couldn’t believe the man I married on a whim was actually wealthy and harbored genuine feelings for me.
A woman sitting on a couch | Source: Midjourney
“Stan,” I finally managed to say, “you’ve really taken me by surprise. I feel like I have feelings for you too, but all this new information is overwhelming.”
He nodded understandingly and guided me to the dining table. We ate the dinner he had prepared.
I shared my feelings with Stan once we finished eating.
“Stan, thank you for such a romantic gesture. No one has ever done anything like this for me in my life.” I felt a tear roll down my cheek as I spoke.
A woman talking to her husband | Source: Midjourney
“I will marry you. That’s my decision now. But could you ask me again in six months? If my decision remains the same, we’ll have a real wedding. Let’s first see how life goes with all of this new information for both of us. You have a tough court battle ahead, and I’ll support you through it.”
Stan’s face lit up with a smile. “I’m so happy. Of course, I’ll ask you again in six months. But will you accept my ring now?”
A ring in a box | Source: Pexels
I nodded, and he slipped the ring onto my finger. We hugged, and for the first time, we kissed. It wasn’t a Hollywood kiss with fireworks and swelling music, but it felt right. It felt like coming home.
As I write this, I’m still trying to wrap my head around everything that’s happened. I married a homeless man to spite my parents, only to discover he’s actually a wealthy businessman with a heart of gold. Life really does work in mysterious ways.
A couple holding hands | Source: Midjourney
If you enjoyed reading this story, here’s another one you might like: When a wealthy man cruelly mocks an elderly woman after a minor accident, no one dares intervene — until Mark, a homeless man, steps forward, demanding respect. The rich man jeers at Mark’s appearance, but the next day, fate flips the script, and he’s on his knees begging for forgiveness.
This work is inspired by real events and people, but it has been fictionalized for creative purposes. Names, characters, and details have been changed to protect privacy and enhance the narrative. Any resemblance to actual persons, living or dead, or actual events is purely coincidental and not intended by the author.
The author and publisher make no claims to the accuracy of events or the portrayal of characters and are not liable for any misinterpretation. This story is provided “as is,” and any opinions expressed are those of the characters and do not reflect the views of the author or publisher.
Leave a Reply