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.

23 Backhanded “Compliments” That Are Actually Insults

 Everyone has been guilty of giving compliments that turn out to be less-than-sincere upon closer inspection. However, backhanded “compliments” are some of the worst, especially since they’re disguised as sweet remarks. It’s important for friends to be honest with each other, of course, but couching hard truths in fake compliments is rarely the way to go. (Unless you’re auditioning for a Real Housewives franchise, of course, in which case you can carry on.) If you’re ever on the receiving end of a backhanded compliment from a friend, the real meaning might not even sink in until hours, or even days, later.

While backhanded compliments typically stem from the speaker’s own insecurities, that doesn’t make them any less hurtful, says Sherese Ezelle, LMHC, LCPC, a licensed behavioral therapist. And when they come from a friend, a backhanded compliment is likely to sting even more — and may even damage your relationship.

Backhanded compliments run the gamut from clueless comments to rude remarks, and can also be a form of microaggression, Ezelle says. If it seems like your pal has crossed a boundary, she recommends disputing their comment in the moment by calmly asking for more info. “More often than not, to challenge them on the spot allows for the individual delivering the ‘compliment’ a chance to defend or further explain their intent,” Ezelle tells Bustle. “You want to be sure to give an opportunity for conversation so that growth can happen and friendships can be preserved.”

Of course, different friendships have different dynamics. Some close friends tease each other mercilessly and, as long as everyone’s on the same page, it tends to be OK. That said, it’s alright to recognize when something feels more hurtful than funny, or more like passive-aggressiveness than silly banter, Ezelle says. If backhanded compliments seem to be a habit rather than an exception, you can always tell your friend to buzz off — or look for a new friend circle.

These 23 backhanded compliment examples can help remind you of what a barely-concealed dig really sounds like. That way, the next time your friend claims to love your outfit or announces that they find your apartment “cozy”, you’ll know exactly how to handle it.

1. “Your Instagram Makes You Seem So Fun!”

Why it’s backhanded: On the one hand, it’s good to know all your careful filtering and captioning haven’t been in vain. But when your friend says your Instagram seems fun, they may be implying that the real you is much less interesting than the image you’re trying to project.

How to respond: “Because I am fun!”

What they could have said instead: “I’m so inspired by the way you curate your feed. It really shows off your creative side.”

2. “You Look So Great In That Photo. I Can’t Even See Your Acne!”

Why it’s backhanded: The nice compliment is immediately weighed down by the acne comment. They’re basically saying you typically have a flaw, but in this photo, you only look great because that flaw is removed. “It would be particularly hurtful if you also had an insecurity about your complexion,” says Sarah Dumoff, LCSW, a psychotherapist and founder of private practice here/now.

How to respond: “Thanks. I love this picture too, though I feel good in photos even when my skin isn’t ‘perfect.’”

What they could have said instead: “Omg, you look amazing!”

3. “I Didn’t Expect You To Get The Job. Congratulations!”

Why it’s backhanded: When a friend makes a point of mentioning their low expectations, it takes away from their congratulations.

How to respond: “I worked really hard for this. Go me!”

What they could have said instead: “I was rooting for you and am so relieved it went well!”

4. “You’re So Independent. It’s No Wonder You Haven’t Found Someone Yet.”

Why it’s backhanded: Among all the things ambitious people are tired of hearing, this is probably the most common. In theory, such a remark compliments your sense of autonomy; in practice, it implies that your independence is driving potential significant others away. As an added bonus, it perpetuates the idea that you have to compromise your sense of independence in order to be attractive. Yikes.

How to respond: “Yup! And I’ll know someone’s right for me when they respect that.”

What they could have said instead: “If you ever want to get back into the dating pool, I know someone’s going to fall immediately for your drive.”

5. “I Love How You Don’t Care How You Come Across.”

Why it’s backhanded: Your friend may profess to love your devil-may-care attitude, but what they’re really saying is that they think you’re too “out there.” Either that, or they’re making a salty comment because they’re envious of your laid-back attitude.

How to respond: “Yes! It’s taken a lot of work to get my confidence to this level. I try not to focus on what others think anymore.”

What they could have said instead: “You always seem so confident and relaxed. Tell me all your secrets.”

6. “I Wish I Was As Chill As You About All This Clutter.”

Why it’s backhanded: The real translation may be, “Your place isn’t cleaned to my exact standards and I need you to know that.” Regardless of their intention, it’s rude to make comments when you’ve been invited into someone’s private space.

How to respond: “Really? What would you do differently?” Sometimes asking someone to explain their comment is a way to get them to pause, reflect, and realize they’re being mean.

What they could have said instead: “Thanks for having me over!”

7. “That New Haircut Looks So Much Better Than Your Old One.”

Why it’s backhanded: They’re right — your new ‘do does look fabulous. But no need to be rude about what you looked like literally an hour ago. It may also make you wonder how long they’ve secretly disliked your hair.

How to respond: “I’m all about changing up my look. I’ve loved all my hairstyles and this one’s great, too.”

What they could have said instead: “Wait, this so, so good.”

8. “I Love How You’ll Just Wear Anything.”

Why it’s backhanded: If you’re getting ready together, chances are this comment is constructive and your friend is trying to prevent you from leaving the house in a not-so-great look. If they make this comment once you’re already out, however, that’s when it’s officially rude — and it might even plant a seed of self-doubt that ruins your whole night.

How to respond: “Is that a hint? What’s wrong with my outfit?” You can be honest with each other, laugh it off, and ask if they’d like to offer some advice.

What they could have said instead: “Hold up, hold up. Do you still have those wide-leg pants? Those would be perfect for tonight.”

9. “I Would Never Be Able To Pull Off That Outfit!”

Why it’s backhanded: While it sounds like they’re admiring your style, your friend is likely saying they wouldn’t be caught dead in anything similar.

How to respond: “Thanks, yea. I’ve been feelin’ myself lately. I’m all about the cargo pants trend. Can you believe they’re back?” This is a way to brush off their comment and show your friend that your “weird” look is deliberate — and fashionable.

What they could have said: “Ugh, I can’t keep up with trends. Can you share your Pinterest with me?”

10. “You’re So Charming When You Make An Effort.”

Why it’s backhanded: Great! You’re being charming and suave right now. Mission accomplished. But what about when you’re lounging in your soft pants? Your friend is kind of saying that you’re not usually this charismatic.

How to respond: “I don’t always feel the need to be ‘on’ around my close friends, but sure, I can pull out the charm when need be.” You can also mention that their comment was hurtful. Remember, when in doubt, call it out.

What they could have said: “Bestie, you’re a shining star of wit and charm.”

11. “You Look So Professional With Your Hair Straight.”

Why it’s backhanded: Talk about microaggressive “complimenting” styles. On one end of the spectrum, they’re announcing that they believe you usually look bad or unkempt. On the other, they’re saying curly or natural hair is somehow unprofessional. And that’s not OK.

How to respond: “Well, I’m glad to know that you think my natural hair makes me look so unprofessional.”

What they could have said instead: Nothing. Or, “Did you do something different with your hair?”

12. “I Wish I Didn’t Have Any Responsibilities Like You.”

Why it’s backhanded: People might be inclined to say this to their friends who live with their parents or to those who don’t have kids. Living rent-free or child-free can be less stressful than many alternatives, but that doesn’t mean anyone’s life is totally carefree or without responsibility. Saying otherwise is passive-aggressive at worst and presumptuous at best.

How to respond: “Oh wow, do I make it look that way? I have a million plates spinning at once. How are things going on your end?” This will get to the real root of the issue, which is that they’re overwhelmed.

What they could have said instead: “Do you have any spare time to listen to me vent? I’ve been so stressed lately.”

13. “Your Place Is So Cozy.”

Why it’s backhanded: Calling someone’s apartment “cozy” is often code for “super tiny” or even “so tiny I don’t understand how you live here.” It’s also condescending since not everyone can afford a sprawling abode — or wants to live in one. It just isn’t what you want to hear when you’ve invited folks over for a housewarming.

How to respond: “Thank you! I put a lot of work into the decor. Wait, did you see my record player over here?”

What they could have said instead: “Thanks so much for having me over! I always love how you decorate. Oh! I brought a quiche.”

14. “You’re Coping With This So Much Better Than I Thought You Would.”

Why it’s backhanded: You’re literally on your couch in a onesie surrounded by tissues and rubbing at your puffy eyes — and this is better than what your friend thought? How did they expect you to deal with a breakup? You might not want to know.

How to respond: If you can muster some cheekiness, say, “Thanks for the vote of confidence, pal.” If you’re too upset say, “I just need someone to listen to me, if that’s OK.” Also, side note: If a certain friend isn’t supporting you the right way during a tough time, try reaching out to someone else. Another friend, family member, or therapist may be a better bet.

What they could have said instead: “What you’re going through is one of the toughest things ever. You’re handling it so well, but it’s also OK if you need to take more time for yourself.”

15. “You Look So Much More Awake With Makeup.”

Why it’s backhanded: Your friend may be trying to give you a compliment, but this one sends the message that you usually look bad or tired whenever you deign to go outside without blush or mascara. It might be their way of judging — or they simply might not realize why it’s a rude thing to say.

How to respond: “Wait, what do I normally look like?”

What they could have said instead: “I need that blush. Where’d you get it?”

16. “You Look Refreshed Today. I Almost Didn’t Recognize You!”

Why it’s backhanded: According to psychologist Dr. Roberta T. Ballard, Ph.D., this is a common backhanded compliment. It’s something you might hear from an office friend who means well, but doesn’t realize they’re implying you usually look messy or tired. Not to mention, it’s never smart to comment on someone’s appearance, especially if you don’t know what’s going on with their health or personal life.

How to respond: “Thanks. Guess it was that extra cup of coffee I had today.” And leave it at that.

What they could have said instead: “That color blue looks amazing on you.”

17. “You’re So Chill In Your Relationship.”

Why it’s backhanded: “It may be innocent admiration of your patience in your relationship, or it may feel like something else is being implied,” says Lauren Spinella, LPC, a licensed mental health therapist and owner of Peaceful Path Counseling. Are they really impressed by your patience during a tough time in your relationship, or are they implying you’re a doormat?

How to respond: “Do you feel like I’m too chill?” According to Spinella, it’s totally fair to ask for some genuine clarification in a non-accusatory way. That’ll open the door to a deeper convo.

What they could have said instead: “I really admire how patient you are. I’m also a little concerned that you’re dealing with so much and want to make sure you’re OK.”

18. “You Look Great For Your Age!”

Why it’s backhanded: While this one’s often said with the best of intentions, it’s steeped in ageism and the idea that you can only look good if you look young. “Sometimes the person giving the backhanded compliment might not have the intention of saying something hurtful, however, the impact is still there,” says therapist Emily Sharp, MA, LCAT, ATR-BC, RYT-200.

How to respond: “I’m sure you didn’t intend to, but when you make comments about my appearance it makes me uncomfortable.” Sharp says this will get the message across in a diplomatic way.

What they could have said instead: “You look great!”

19. “You’re So Articulate.”

Why it’s backhanded: Calling you articulate is a way to express shock that you said something intelligent. It has the same vibe as, “Wow, I didn’t expect you to be good at this.” The “you’re so articulate” comment also comes with a long history of racism, especially when aimed at Black people, Ballard says.

How to respond: “What did I say that surprised you?” Again, asking someone to explain their comment is a subtle way of calling them out.

What they could have said instead: Nothing. Or something like, “It’s always such a pleasure to talk to you. I’m glad we ran into each other.”

20. “You’re So Pretty. I Don’t Get Why You’re Still Single.”

Why it’s backhanded: This backhanded compliment can send your brain swirling through a list of possible meanings. Are they saying something else is wrong with you? Or that you’re incomplete until you meet a partner? Whatever it is, it won’t feel good.

How to respond: “How are the two related?”Depending on the type of relationship you have with your friend, you can straight up call them out or ignore them, Sharp says. “You can also respond to a portion of the backhanded compliment that feels genuine, in order to maintain positivity,” she tells Bustle. “Everyone handles these situations differently, but the important part is validating your feelings for yourself.”

What they could have said instead: “We haven’t chatted about our dating lives in forever! Are you talking to anyone or nah?”

21. “I Love Your Nails. It Must Be Nice To Have So Much Extra Time In Your Day To Pamper Yourself.”

Why it’s backhanded: “This may be an innocent comment,” Spinella tells Bustle. “But it’s also understandable for someone to be put off by hearing it. You might think, are they implying that I don’t have a lot going on or that I am prioritizing the wrong things?”

How to respond: “What do you mean?” While it’s often possible to glean the intent of a backhanded compliment, Spinella says it’s best to ask for clarification, especially if the words hurt.

What they could have said instead: “I love how you did your nails! It can be so hard to prioritize self-care with a busy schedule. Maybe you can help me do the same?”

22. “You Look So Comfortable!”

Why it’s backhanded: This isn’t a real compliment, says wellness coach Dr. Cali Estes. Instead of saying what they really think, it’s a roundabout way for your friend to indicate that they don’t like your outfit or that they think it’s inappropriate for a situation.

How to respond: “Thanks! I’m so grateful to be comfortable so I can fully enjoy myself at this wedding.”

What they could have said instead: “I love your outfit. I really wish I would have chosen something more comfortable, too.”

23. “You’re Incredible For Working That Hard! I Could Never Leave My Cat Alone All Day.”

Why it’s backhanded: While it feels like they’re complimenting your work ethic, what they’re actually doing is commenting on your choices as a caretaker. This one’s also commonly aimed at new moms, according to Dr. Anisha Patel-Dunn, DO, a psychiatrist and chief medical officer of LifeStance Health.

How to respond: “What do you mean by that?” Patel-Dunn recommends asking for more info. For instance, “Ouch, I feel a bit hurt by that comment. Can you clarify what you mean because this is what I heard…”

What they could have said instead: “You’re the queen of getting stuff done. How do you do it?”

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