Dating Gone Wrong – 10 Real-Life Worst Date Stories Of Women

Written by: Kassandra Dizon

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Time to read: 11 min


Have you ever had a bad dating experience that left you questioning the modern dating world? I know I have. The pitfalls of modern dating can be tricky to navigate, with misrepresentation, catfishing, safety concerns, ghosting, and scamming lurking around every corner. I will talk about 10 real women's worst dates in this article, which will show you the problems we face when we are dating these days.


The Digital Masquerade of Bad Date Stories


In my journey through the wild world of modern dating, I've seen my fair share of digital trickery. Misrepresentation and catfishing are everywhere, turning what should be a chance to connect into a mess of lies. 


Catfishing

A girl wearing a masquerade

I remember the thrill of matching with someone who seemed perfect, only to find out their profile was fake and their intentions were shady. This wasn’t just a letdown; it was a harsh reminder of how vulnerable we are when we open up online.


Catfishing, in particular, caught me off guard. It’s a game where people create fake personas to trick others. I’ve heard bad date stories, and, embarrassingly, I’ve been through it myself, finding out the person on the other end was completely made up.


These experiences taught many women like me that behind a nice profile picture and a clever bio, there can be a very different reality. The trust I placed in these online interactions was shattered, leaving me to pick up the pieces and question future connections.


In my twenties, after relocating from Boston to New Jersey for work, I started online dating to meet new people. I connected with a seemingly nice guy and we had good conversations, phone chats, and exchanged pictures. He repeatedly asked about my fitness and if I was fat, which made me self-conscious. When we finally met in person, I was shocked to find he looked nothing like his photos—he was bald and significantly heavier. His deception scared me, and I left immediately. It wasn't his appearance that bothered me, but his manipulation.

C.S. Friedman

Navigating Misrepresentation


The challenge isn't just spotting the catfishers and fakers, but understanding why they do it in the first place. It’s a sign of the bigger problems in our digital dating culture, where the pressure to impress can make people create more appealing but less real versions of themselves. This realization has made me understand those who feel they need to misrepresent themselves, even as I stay on guard against their lies.


Navigating modern dating with all its digital disguises has been a journey of growth, caution, and resilience. The road to finding real connections is full of challenges, but facing these issues is a step toward more genuine interactions in our increasingly virtual world.


The Ghosts of Relationships Past

"The Ghosts of Relationships Past" looks at how our old romantic experiences can still affect us today. It dives into how past betrayals, disappointments, and unresolved feelings can linger, making it hard to trust and connect with new partners. This section talks about why it's important to deal with these leftover emotions to build healthier, happier relationships in the future.


Safety Concerns


When you're meeting someone new, there's always that worry in the back of your mind. You don’t know if they’re who they say they are or if they have good intentions. 


The thought of encountering someone dangerous can be terrifying. It's not just about worrying whether the person looks like their profile picture—it's about wondering if you’ll be safe with them. That anxiety is a huge part of modern dating, and it’s something you have to take seriously.


I have, although it was years ago, and it really was not the worst thing which could have happened. I'll refer to the guy as “Mahesh”, and let's just say that he lived in an area of the world which isn’t known for having the best treatment of women. His first message to me was a request for nude photos, and he was a bit crass/vulgar about the way he worded things. I responded to Mahesh with something about how I was looking to chat with guys who had more respect for women, and that apparently enraged Mahesh, so he made a threat about having me gang-raped by dogs in a public area if I ever contacted him again. I didn’t take Mahesh’s threat seriously, but his actions were against the terms of that dating website, so I reported him to the administrators. I’m not sure what, if any, action was taken, because they never responded to me, and Mahesh’s profile stayed up.

Barbara

Ghosting


People who have experienced ghosting have learned a tough lesson in vulnerability. When someone vanishes without a word, it leaves a deep silence, unanswered questions, and self-doubt.


They've faced this kind of emotional withdrawal many times, each instance eroding their trust in future relationships. Yet, this challenge has strengthened their determination to find relationships based on communication and respect.


Got ghosted the day after we decided to get married. Agreed on how many kids we wanted and everything. Never talked to him again. Left an abyss in my heart, my confidence, and endless questions about why that I never got answered. First time I ever had thoughts about wanting to harm someone. It was an issue for years beyond the time he died (not my doing, his whole family seemed prone to cancer right down to the dog).

Tanya

Scamming


Scamming, on the other hand, presents a different kind of danger. It can be difficult to accept the fact that someone is only interested in you for selfish reasons rather than out of genuine affection. You've encountered scammers whose skill in manipulation is chilling, their intentions veiled behind sweet words and promises. 


These experiences will help sharpen your instincts and teach you the importance of vigilance. Learn to recognize red flags early on and to trust your gut when something feels off.

I am a social worker working with people with mental illness, substance abuse, and homelessness. Recently, I encountered a challenging case involving a senior citizen who receives just over $1000 a month from SSI. She believes she is the fiancée of the lead singer of a famous metal band and has sent him $1000 each month for jet fuel, as he claims his bank accounts are frozen and needs to pay fees. I offered to buy her a ticket to visit him in Vegas but required confirmation from someone who could pick her up, which she refused due to privacy concerns. She insists she has video chatted with him and his attorney, but declined my suggestion to video chat together, claiming her phone only supports two-person video calls. She is in poor health and relies solely on her SSI, which she continues to send to him. I checked AARP scam videos, but they may not be effective. I'm considering a representative payee for her, but she is strongly against it. I'm seeking other methods to help her.

KC

The Labyrinth of Expectations: Pressure, Infidelity, and Cultural Divides


In today's relationships, people often face a maze of expectations, dealing with pressures that can lead to cheating and cultural misunderstandings.


Let's explore how different social norms, personal wants, and cultural differences mix together, challenging couples to balance their values and navigate the complex issues of trust and fidelity.


Pressure


The pressure to impress feels like a heavy burden. I recall dates where I changed so much that I hardly recognized myself, just to meet what I thought were their expectations. It was tiring and made me doubt my value when I couldn't keep pretending. 


This pressure wasn't just about how I looked; it also involved dealing with my own doubts and feeling the societal pressure to find 'the one'. It made every date seem like an audition instead of a chance to truly connect.

Infidelity


Infidelity, on the other hand, is a breach of trust that I've seen unravel relationships around me, sowing seeds of doubt and mistrust. Witnessing friends navigate the aftermath of betrayal, I've learned to tread carefully, aware of the fragile nature of trust. 


It's made me more guarded, yes, but also more attuned to the importance of honesty and loyalty in building a relationship that can withstand temptations and challenges.


I dated a married man once. He was separated from his wife, who was also dating other people. He was passionate and caring, a love I never experienced before. After a year he found out he was expecting his first grandchild who he was told he would not be able to see because of the split. He decided to go back to his wife, however didn’t stay long. It was three miserable years of him flip flopping between me and his wife until I finally had enough. The highs of what I thought was love when he chose me no longer outweighed the lows of loneliness when he chose her. I deserved better and found better. It was incredibly hard to make that decision and stick with it. But the only regret I have is taking so long to make it. It’s rare they ever leave their spouse. Don’t get sucked into the highs, the lows always follow.

Anonymous

Cultural Divides


Cultural divides in dating refer to differences in dating norms, expectations, and practices across cultures. These divides can affect people by creating misunderstandings, conflicts, or feelings of alienation when partners from different backgrounds have differing values or beliefs about relationships. Adaptation and communication are essential to bridge these gaps.


Yes. They used their culture as a bully pulpit to verbally abuse me, instead of accepting me as an equal partner. At first, I didn’t identify what they were doing. Then, I realized they were racist and trying to hurt me by demeaning me, saying “White girls this, white girls that,” even though I’m white and Hispanic. They seemed to have a number of criticisms of part of who I am and I got fed up with it and dumped them. When you enter an intercultural or interracial relationship, one’s culture or race shouldn’t be a consistent topic of discussion or criticism. You should have fallen in love with the person, not the culture or race. And if a person is continually raising your race or culture as a way of putting you down, let them go. They aren’t focused on YOU. They don’t see YOU. They see your race or culture.

Mrs. Perez

Navigating the Social Maze


In today's digital age, the quest for love often leads many to the convenience of dating apps. However, the addictive nature of these platforms, combined with the weight of social and familial expectations, creates a complex social maze. 


Social and Familial Pressures


Social and familial pressures in dating refer to the expectations and influences from society and family members that impact an individual's dating life. 


Starting to date nowadays, people find out it's not just about whether they get along with someone. Social and family pressures make things more complicated. There's this pressure to find a partner, settle down, and do it all within a certain timeframe.


Sometimes, what their family wants or what society thinks a perfect relationship should be like affects them. It feels like they're in a rush and they're being judged, which can overshadow what they really want in a relationship.

Addictive Use of Dating Apps

A hand swiping on a smartphone showing multiple conversations to different people

On dating apps, the fun of matching and chatting can quickly become overwhelming. It's easy to feel disappointed when conversations don't go anywhere. 


These apps can make people feel more alone than connected because they're always getting notifications and seeing lots of potential matches. To deal with this, it's important to limit how much time you spend on the apps and focus on having deeper conversations with fewer people.


This helps you feel more in control and makes dating feel more meaningful. It also helps you balance what you want in a relationship with taking care of yourself.


I quickly lost sight of the purpose of dating apps which was to increase the possibilities of finding someone who I could forge a serious connection with and give me a reason to never look at Tinder again. This particular date was full of awkward silences, even though our text banter was fantastic. She was attractive, but it was obvious she was using photos taken of her years earlier. And who knows? Maybe I wasn't who she was expecting to meet either. The date lasted one drink, and we went our separate ways. My experience finally proved to me everything that’s wrong with dating apps. And that's why I quit cold turkey. There's the catch: You'll never find anything meaningful from a dating app if you aren't looking for anything more meaningful than a date.

Sam Rega

Final Thoughts


When you think about modern dating, it's clear that the road is filled with challenges and learning opportunities. From dealing with deception and ghosting to navigating cultural divides and societal expectations, each experience has been a stepping stone toward personal growth and understanding. You'll learn to be authentic, set boundaries, and prioritize mutual respect. 


Despite the pitfalls, you'll find resilience and a renewed belief in the possibility of meaningful connections. As you continue on this path, you are armed with lessons learned and ready to face whatever lies ahead with an open heart and an empowered spirit.


Related Blog Posts

FAQs

How do dating apps contribute to the challenges of modern dating?

While dating apps offer convenience, their addictive nature and abundance of choices can lead to feelings of loneliness and disappointment, highlighting the importance of setting boundaries and prioritizing meaningful connections.

What are the social and familial pressures in dating?

Expectations from society and family members can create pressure to conform to certain relationship norms and timelines.

How do cultural differences affect dating relationships?

Cultural divides can lead to misunderstandings, conflicts, or feelings of alienation when partners have differing values or beliefs.

What dangers are associated with scamming in online dating?

Scammers manipulate individuals for personal gain, often concealing their true intentions behind sweet words and promises.

What is ghosting, and how does it affect individuals?

Ghosting refers to sudden and unexplained withdrawal in communication, leaving individuals feeling rejected and questioning their self-worth.

How do past relationships affect present ones?

Past betrayals and unresolved emotions from previous relationships can leave emotional scars that affect individuals' ability to trust and form connections with new partners.


These lingering emotions can manifest in various ways, such as being overly guarded, constantly seeking reassurance, or being quick to interpret innocent actions as signs of betrayal. Without addressing and processing these past experiences, individuals may find it difficult to cultivate healthy and fulfilling relationships in the present.

Sources

  • https://www.quora.com/Have-you-ever-been-catfished-online-and-how-did-you-feel-when-you-found-out
  • https://www.businessinsider.com/i-am-addicted-to-dating-apps-2015-2
  • https://www.quora.com/Have-you-ever-dated-a-married-man-or-woman-Did-you-know-that-they-were-married-How-did-it-end

Author

Portrait of Kassandra Dizon

Kassandra Dizon

Kassandra, an intimate wellness advocate, writes upon her rich well of experience to create informative articles and blogs. Her writing is infused with lived wisdom and personal insights, making it relatable and transformative for women and couples alike.Through her work, Kassandra empowers individuals on their intimate wellness journeys. She sheds light on topics that are often shrouded in silence, fostering open conversations about self-care, relationships, and personal growth.

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