Man from Dating Site Brought His Parents on Our First Date with Their Ridiculous Demand – I Decided to Outplay Them

Who brings their parents to a first date? My boyfriend from a dating app did. But what really got me was the list of OUTRAGEOUS DEMANDS his parents brought with them. I knew I’d have to outwit them… but on my own terms.

When I virtually met Jacob on a dating site several months ago, we hit it off instantly. The connection felt real — the kind that makes your heart skip a beat when you see a new message notification. I grew to think that he was “the one,” but then when we actually met… well, let’s just say reality has a way of shattering our perfectly crafted illusions.

A woman holding a phone | Source: Unsplash

A woman holding a phone | Source: Unsplash

Three months of late-night texts and hour-long video calls had built up to this moment. Jacob wasn’t just another match; he was different.

While most guys led with cheesy pickup lines or bland “hey” messages, he had caught my attention with a detailed comment about my profile photo taken at Comic-Con.

“Is that a handmade Scarlet Witch costume?” he’d written. “The detail work is incredible!”

From there, our conversations flowed naturally. He listened, really listened, when I talked about my work as a graphic designer and my dreams of starting my own studio.

A woman using a computer | Source: Midjourney

A woman using a computer | Source: Midjourney

He shared my love for true crime podcasts and could quote every episode of my favorite shows by heart. When I mentioned my sister’s battle with depression, he opened up about his own experiences with anxiety.

“I feel like I can tell you anything,” he’d said during one of our video calls, his warm brown eyes crinkling at the corners. “I’ve never connected with someone like this before.”

“Me neither,” I’d admitted, feeling my cheeks flush. “Sometimes I worry this is too good to be true.”

He’d laughed then, running a hand through his dark hair. “I can’t wait to finally meet you in person. Friday at Coffee Beanz? 7 p.m.?”

A man using a laptop | Source: Pexels

A man using a laptop | Source: Pexels

“It’s a date! Finally!” I’d chirped, unable to contain my excitement.

“See you on Friday!” He said as I hung up, blushing.

I spent the entire week planning my outfit, finally settling on a gorgeous dress that my best friend Sarah insisted brought out my eyes.

“He won’t know what hit him,” she’d said, helping me style my hair.

Friday evening found me standing outside Coffee Beanz, smoothing down my dress for the hundredth time. Through the window, I could see couples enjoying their meals, soft candlelight flickering across their faces.

People in a cafe | Source: Unsplash

People in a cafe | Source: Unsplash

My hands were shaking slightly as I pushed open the heavy wooden door, the warm aroma of garlic and fresh bread enveloping me. My eyes nervously darted around in search of Jacob.

“Lia! Over here!”

I turned toward Jacob’s familiar voice, my practiced smile freezing on my face. There he sat, but not ALONE.

An older couple sat beside him, their faces beaming with smiles. My heart, which had been filled with excitement all day, sank to my stomach.

“Hey… um, hi, what’s going on?” I managed, my brain struggling to process the scene before me.

A shocked woman | Source: Pexels

A shocked woman | Source: Pexels

Jacob stood up, his bright smile unchanged as if this was completely normal. “Lia, I’m so excited to finally meet you! These are my parents, Linda and Patrick!”

Linda, a petite woman with perfectly coiffed gray hair and gold earrings that probably cost more than my monthly rent, gave me a practiced smile that didn’t reach her eyes. Patrick, sporting a dress shirt that seemed a size too small for his frame, barely looked up from his menu.

“Sit down, girl,” Linda patted the chair next to her, not next to Jacob. “While we wait for our appetizers, I have a few questions for you.”

An older lady smiling | Source: Midjourney

An older lady smiling | Source: Midjourney

I sank into the chair, still trying to make sense of this ambush. The waiter appeared with water glasses, and I found myself wishing it was something stronger.

That’s when Linda pulled out a crisp sheet of paper from her designer handbag.

“Now then,” she cleared her throat, clicking her gold-plated pen. “I’ve prepared a brief questionnaire to help us get to know you better. I want you to fill it out.”

Sheets of paper on a table | Source: Pexels

Sheets of paper on a table | Source: Pexels

My eyes scanned the paper she placed before me, each question worse than the last:

1. What is your current annual income and five-year career projection?

2. Please list any medical conditions, including a family history of genetic disorders.

3. How many romantic partners have you had, and what were the reasons for those relationships ending?

4. Do you own or lease your vehicle? What is your credit score?

5. Are you willing to sign a prenuptial agreement?

6. Do you plan to work after having children? If so, who will provide childcare?

7. What is your stance on living with in-laws?

8. Are you willing to host special occasions like Thanksgiving & Christmas every year without expecting a penny from your partner?

A startled woman covering her mouth | Source: Pexels

A startled woman covering her mouth | Source: Pexels

The questions went on and on like a never-ending train carriage. My water glass stopped halfway to my mouth. “I’m sorry, but is this for real?”

“Of course it is, dear,” Linda replied, her tone suggesting I was being deliberately difficult. “Our family has certain standards to maintain. We need to ensure any potential partners for our Jacob are… suitable.”

My eyes darted to Jacob, waiting for him to jump in, to say this was all a joke. But he just sat there, examining his napkin as if it held the secrets of the universe.

A man sitting casually | Source: Midjourney

A man sitting casually | Source: Midjourney

Something snapped inside me. Three months of building this connection, sharing hopes and fears, only to be treated like a job applicant? No. This called for a different approach.

“Would you excuse me for just a moment?” I smiled sweetly. “Ladies’ room.”

Instead of heading to the restroom, I ducked into the convenience store next door. Five minutes later, I returned with my own notebook and pen.

“Before I answer your questions,” I said, sitting down with renewed confidence, “I have a few of my own.”

A woman holding a piece of paper | Source: Pexels

A woman holding a piece of paper | Source: Pexels

Linda’s perfectly plucked eyebrows shot up in surprise as I placed the paper with my questions on the table. She picked it up and began reading loudly, her face speaking volumes of her anger.

“Question one: At what point did you realize your son wasn’t capable of choosing his own partner?”

Patricks’s face reddened. Jacob finally looked up from his napkin.

“Question two: How many women have actually completed your interrogation process? Or do most run screaming before the credit check?”

“This is completely inappropriate!” Linda’s voice pitched higher as she continued to read.

A furious older woman with a man | Source: Midjourney

A furious older woman with a man | Source: Midjourney

“Question three: Do you also inspect their teeth like show horses, or is that saved for the second date?”

“Question four: When Jacob moves out of your basement, will you be requiring his future wife to submit weekly progress reports?”

“Question five: Have you considered therapy for your control issues, or is that too personal a question?”

“That’s enough!” Jacob slammed his hand on the table, making the silverware jump. “You have no right to disrespect my family like this!”

An angry man | Source: Midjourney

An angry man | Source: Midjourney

I leaned back, crossing my arms. “Oh, but they have every right to treat me like I’m applying for a position at the FBI?”

“My parents are just looking out for me,” he protested, his voice weak. “They want what’s best— “

“No, Jacob. What’s best for you would be growing a backbone and living your own life.”

Linda and Patrick were already gathering their things, faces flushed with indignation. Linda’s hands shook as she stuffed her questionnaire back into her bag.

“We’re leaving,” she announced. “Jacob, come on. She’s not the one for you.”

“Wait!” I called out, loud enough for nearby tables to turn. “Aren’t you forgetting something?”

Side shot of a woman | Source: Midjourney

Side shot of a woman | Source: Midjourney

They paused. “WHAT??”

“Waiter, these people are trying to leave without paying their bill!” I announced loudly, waving to the waiter. “Guess running out on checks is another proud family tradition!”

The restaurant had gone quiet. Linda’s hands shook as she pulled out her credit card, practically throwing it at the waiter. I stood up, smoothing my dress once again.

“Well, this has been entertaining. I’ll cover my water.” I placed a five-dollar bill on the table and turned to Jacob.

“Good luck finding someone who meets your family’s rigorous standards. Although, you might want to try job recruitment sites instead of dating apps. I hear they provide detailed background checks and references.”

A woman laughing | Source: Midjourney

A woman laughing | Source: Midjourney

As I walked out into the cool evening air, my phone buzzed with a message from Jacob, “You didn’t have to be so cruel. My parents were just looking out for me.”

I typed back, “Just looking out for myself, mama’s boy. Goodbye!”

Later that night, Sarah called to hear about the date. After I finished telling her everything, she was quiet for a moment.

“You know what?” she finally said. “I bet Linda has a spreadsheet ranking all of Jacob’s potential wives.”

We both burst out laughing, and I felt the last of my disappointment melt away. Dodged a bullet? Absolutely. And I’ve never been so grateful for a red flag wrapped in a questionnaire.

A woman walking away | Source: Midjourney

A woman walking away | Source: Midjourney

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.

Preparing for the Impact of Hurricane Milton: Evacuation Areas & Essential Safety Measures

They have recommended that everyone in a household is familiar with the hurricane plans they’ve made. This may include catering for those at work, children’s daycare, and other frequently visited locations such as grocery stores.

Additionally, the government suggests that households should stock adequate supplies. Some recommended items are medications, disinfectants, and pet supplies that are carried in the go-bag or car trunk. Access to these supplies may be limited for days or even weeks after a hurricane.

Households also need to clear drains and gutters, secure outdoor furniture, and consider installing hurricane shutters. It is highly valuable to charge a cell phone and invest in backup charging devices for electronics when a hurricane is forecasted.

2. Stay Informed

In this step, it’s crucial for households to know if they live in an evacuation zone, listed at the end of this article, as they may need to evacuate quickly due to a hurricane. They should familiarize themselves with evacuation routes. They can also practice evacuating with their household and pets, and determine where they will stay.

Households should follow the guidance of local emergency managers, who collaborate with state, local, tribal, and territorial agencies. They will provide up-to-date recommendations based on the specific threats to your community and the necessary safety measures.

3. Check On Your Neighbors

Reach out to your neighbors, especially seniors or those who may require extra assistance, to ensure they have adequate hurricane plans in place. Offer your help in securing their preparations and provide support wherever needed.

4. Stay Out of Flood Water

Households should avoid entering floodwaters, as even six inches of fast-moving water can knock people off their feet. They should prioritize their safety and steer clear of any flooded areas.

5. Turn Around and Do Not Drown

People should be aware that just one foot of moving water can easily sweep away a vehicle. They should stay vigilant and avoid driving through flooded areas. Avoid walking, swimming, or driving through flood waters at all times. When encountering such a scenario, they should turn around.

6. Take Care of Your Mental Health

Lastly, individuals should prioritize their mental health during and after a hurricane. It’s important to acknowledge any feelings of anxiety or stress and seek support if needed. Connect with friends, family, or mental health professionals to discuss your concerns and find coping strategies.

Tampa Mayor Jane Castor has emphasized the need for households to pay attention to the evacuation zones as Hurricane Milton approaches Florida’s west coast. She warned the residents, “I can say without any dramatization whatsoever: If you choose to stay in one of those evacuation areas, you’re gonna die.”

Tampa is located in Hillsborough County. The region has listed compulsory evacuation orders for those in Zones A and B, as well as those who live in mobile homes. Tampa has urged residents of these areas to evacuate as Hurricane Milton is “literally catastrophic.”

Evacuation Zones

Charlotte County: It has issued a mandatory evacuation order for residents in Red Zone-A and Orange Zone-B, including those living in mobile and manufactured homes.

Citrus County: It has given a mandatory evacuation order that began on October 8, 2024, for all residents living in campers, tents, mobile homes, manufactured homes, or any structures unable to withstand sustained winds of up to 110 MPH.

Collier County: A voluntary precautionary evacuation is effective immediately for all residents in Collier County in Zones A and B. This includes west of Airport Pulling Road and south of US-41 Tamiami Trail E.

The order covers mobile home residents and areas with a history of storm flooding. A mandatory evacuation for all of Zones A and B began on October 8, 2024.

DeSoto County: It has issued evacuation orders for Zones A (Red) and B (Orange). These areas affect all residents living in mobile and manufactured homes, as well as those in low-lying or flood-prone areas.

Clay County: Currently, there are no mandatory evacuation orders, but residents in low-lying or flood-prone areas, especially along Black Creek or the St. Johns River, are strongly encouraged to consider relocating for safety.

Hardee County: On October 7, 2024, Hardee County Emergency Management advised residents in low-lying areas, mobile homes, recreational vehicles, and unsafe structures to evacuate as soon as possible.

Glades County: This county has implemented a voluntary evacuation for mobile homes, RV parks, and low-lying areas, which started on October 8, 2024.

Hillsborough County: This county has announced a mandatory evacuation for Evacuation Zones A and B, including all mobile homes and manufactured housing throughout the county, which started on October 7, 2024.

Hernando County: Mandatory evacuation orders for all areas west of US 19, including evacuation zones A, B, and C began on October 8, 2024. This includes all residents in coastal and low-lying areas, as well as those in manufactured homes countywide.

Levy County: A mandatory evacuation is in effect affecting all mobile homes, manufactured homes, recreational vehicle parks, coastal communities, and low-lying areas west of US 19. Hurricane risk shelters have opened at Bronson Elementary for special needs and Bronson Middle High School for general population/pet-friendly evacuations.

Lee County: It has issued mandatory evacuation orders for Zones A and B, urging residents to finalize emergency plans and evacuate as soon as possible. They should aim to be in a safe location by the evening of October 8, 2024.

Manatee County: This county has issued a mandatory evacuation for all residents in Levels A, B, and C, including visitors in RVs or mobile homes, effective October 7, 2024.

Marion County: The Marion County Sheriff’s Office Emergency Management officials have recommended evacuation for residents living in mobile homes, RVs, modular-type homes, and site-built homes constructed before 1994 due to the hurricane’s projected path.

Miami-Dade County: This county has announced a voluntary evacuation center for residents of mobile home parks, opening the E. Darwin Fuchs Pavilion on October 8, 2024, as a pet-friendly evacuation option.

Okeechobee County: A voluntary evacuation has been issued for all low-lying areas and mobile homes starting October 8, 2024.

Pasco County: This county has mandated evacuations for Zone C as the hurricane approaches. Evacuations are required for those in Zones A, B, or C, as well as residents in manufactured homes, RVs, low-lying areas, or structures prone to flooding.

Volusia County: A mandatory evacuation order took effect on October 9, 2024, for all areas east of the Intracoastal Waterway, including residents in manufactured and mobile homes, low-lying and flood-prone areas, as well as campsites and RV parks.

Sumter County: Residents in mobile homes, low-lying areas, or with special needs are strongly urged to consider evacuation or relocating to a shelter when they open.

Sarasota County: Residents in Sarasota County living in Level A or near Level A, as well as those in manufactured home communities or mobile/boat homes, are advised to implement their evacuation plans immediately, whether that involves staying with friends or leaving the area.

Pinellas County: Pinellas County has enacted a mandatory evacuation order for all residents in Zones A, B, and C, as well as all mobile homes. Special needs residents and residential healthcare facilities in these zones are also included in the evacuation order.

Putnam County: A recommended evacuation has been issued for Zones F and A due to concerns regarding high river levels.

Obeying the directives issued by local authorities and noting the evacuation zones ensures that families can evacuate safely and efficiently. This also allows emergency services to respond effectively to those in need.

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