Dating can be awful. It's bad enough when we have to endure bad dates, but when it's our friends or family members who are in the line of fire, sometimes all we can do is be neutral about their situations and hope that they will eventually get a clue. After all, we wouldn't want to intrude on affairs that aren't ours to deal with. The following Redditors, however, couldn't stand idly by—they called out their loved ones or their awful choice of partners, and hopefully, we can all learn a lesson from their experiences.
1. A Terrible Plan
My brother dated a girl who pretended to have cancer when she thought he was going to break up with her. Her parents went along with it. Here's the crazy part, though—my dad is an oncologist, so this girl could have chosen any other disease to lie about, but she still went with cancer. My dad was asking for the name of her doctor and offered to help her out.
She was strangely vague and dismissive. We all felt suspicious and we felt bad for doubting her. It took six weeks, but my brother managed to get her mom alone. He questioned her a little and found out her daughter wasn't sick. Well, at least not physically.
2. Not A Great Plan
My son’s girlfriend lost her mind when he broke up with her. She sent thousands of messages to him and spammed his phone with calls. He had to get a no-contact order against her and also press charges. She then threatened to report him in retaliation—that was a big mistake on her part. At one point, two detectives showed up at my door to question me and my son.
Luckily, she was dumb enough to admit her full plan in a text message, in which she also acknowledged that he never did anything to her. She also mentioned that she was hurting herself to make false evidence of bruises and scratches. We were all in lockdown, so neither of them had left the house for seven weeks, making it impossible for him to have done it.
She wasn’t very smart, but it was still the worst two weeks of our lives waiting for the results of that investigation. He is taking a break from dating now. He sure can pick them.
3. Don’t Judge A Book By Its Cover
My sister and I were very close to our uncle growing up. He was the guy who pretended to be Santa and the Easter Bunny for us. He got engaged to this woman named Christine. I remember she was incredibly beautiful, but also incredibly jealous and not mentally well. My sister and I didn’t know this at the time.
Our interactions with her were minimal but positive. In truth, she looked like a Disney princess. For various reasons, including my family’s dislike of her jealousy, my uncle broke off their engagement. A few days later, I happened to notice something moving fast outside. I peeked through the blinds, and my stomach dropped—it was Christine out on our front lawn.
When I told my mom, I saw the blood drain from her face. She told me to go to my room and whispered to my dad to call the authorities. Long story short, Christine had threatened to harm all of us if my uncle broke up with her. When she showed up at our house, she was threatening to burn it down.
4. Trust Me On This One
I saw one of my girls spending a lot of time with someone I didn't approve of, and I felt compelled to step in. I work for the happier side of my state's human services agency, but we still share a lot of our customers with Child Welfare. I have a pretty good memory for names and faces. And within the department, we talk quite a bit.
I will occasionally run into a family whom I already know an uncomfortable amount of private information about, but generally, it doesn't affect the decisions I have to make aside from who it gets assigned to next. One day, my daughter came home talking about this boy she'd met, and I recognized his first name immediately because it was uncommon. When she told me about him, my blood ran cold.
I asked her, "You're talking about David, right?" She gave me this really confused look and said yes. I told her, "Ok, kiddo, look. I can't discuss the reasons for this. I know you like this kid, but the answer is absolutely not. You are not to hang out with him or his circle of friends. I need you to trust me on this because I can't tell you anything about my reasons for it".
She started protesting, but my answer was still no. It wasn't until nearly six years later that she learned about his history as a juvenile delinquent, which included a great number of unsavory things.
5. He’s Still Got It
My sister was dating a holistic healer and massage therapist whilst my dad had metastatic cancer. He kept talking about an alkaline diet and all this "good energy" nonsense when my dad was clearly terminal. This guy bought my niece a book called "Healing With Faeries". He talked about it in my dad’s room. My dad was mostly gone at this point.
He hadn't spoken or been meaningfully responsive in days. But after hearing this, he took us all by surprise—he opened his eyes and said, clear as day, "Healing with Faeries? Is that the name of your little back rub business?" Then went back to sleep.
6. People Aren’t Games
My sister dated an absolutely awful human being. In the beginning, he seemed relatively decent to her. He was very intelligent and good-looking from a seemingly nice family. My sister is one of those people that puts her whole heart on the line in any relationship and the people around her know that she is very genuine and compassionate.
This guy basically entranced her, led her on for eight months through letters and phone calls while he was abroad, and then when he got back, he treated her badly for a few weeks. He used her for money and transportation, and he often tried to pick fights with her. She was really confused and tried to talk to him about what was going on. His response was appalling.
He told her that everything they had was a fling and he didn't care about her at all. She was absolutely devastated. He basically played her for his own amusement and my sister went through some major depression and trust issues after dating that guy. She started drinking, became very reclusive, gained a lot of weight, and gave up on her hobbies.
She finally got herself out of the rut and she's now engaged to a really great man, but my entire family was really worried about her for a long time.
7. Such An Unnecessary Excuse
My friend dated a super strange guy for nearly two years. He claimed to have a brain tumor. But here's the weird part—she never saw him take the loads of meds he claimed to have, and when she asked to see his meds, he would accuse her of not believing him. He even supposedly had brain surgery one day, and the next day, he was back to normal and fully functioning.
He wouldn't let her know which hospital he was having surgery in. We found out the truth after they broke up. No surprise, he was cheating on her the whole time when he had a "doctor" appointment or "surgery".
8. A Continued Lack Of Judgment
My daughter’s boyfriend Adam was a piece of garbage and we knew it from the moment we met him. He constantly told us how mature he was, simply for being two years older than our daughter. We’re actually adults, son. You’re all immature in our eyes. I have a list of the things Adam didn’t like about her, but I really don’t know what he did like.
The very first time we met him, my daughter had told him that I’d be dyeing my hair. Adam's next move made my blood boil—he came up behind me at the kitchen sink, ran both his hands through my hair, and asked me if I’d like his help to dye it. I locked myself in the bathroom to dye my hair without the uncomfortable help.
Adam took this time to talk to my husband in the kitchen and informed him that the back door is actually the pleasure center of a man’s body. We all thought this was a very strange topic to discuss upon the first time meeting your girlfriend’s parents. At this point, I was sending my daughter a few hundred dollars a month for groceries.
One night, Adam called me around midnight and berated me like he was my parent because I didn’t send her enough money. I told him that matter was between me and her. When they finally broke up, I learned that she bought 100% of all groceries and all restaurant meals for the entire relationship.
9. Weird Choices
My brother was in a weird situation with his previous wife. She didn’t want him to be attractive to other women, so she made him change his look in a shocking way—she forced him to shave his head. She told him if he ever left her, she would start selling her body. After my dad went and rescued him, she harassed everyone who had a remote connection to him for years. He’s remarried and happy now.
10. The Partner Isn’t Always The Problem
My boyfriend's mom thinks I'm the worst person on Earth because apparently, I've brainwashed him into believing he's mentally ill...All I did was suggest that he get mental health help because he had been showing erratic behavior lately. She would end up eating her words though—just recently, he was officially diagnosed with a specific illness and is on the proper medication now. He also sees a therapist and is much happier.
Despite all that, his mom still doesn't believe mental illness is real.
11. Young Love Can Be A Mistake
My younger brother’s first real long-term girlfriend was really manipulative, and I used to encourage him to break it off, which caused some fights between us. She was possessive, controlling, and used her own mental illness and trauma as a way to guilt him. Eventually, things reached a point of no return—she ended up cheating on him with one of his close friends and got pregnant.
As awful as she was, I’m so grateful that she was at least honest about the kid not being his right off the bat. My brother was still pretty broken up by it, but our whole family was so glad when it was over.
12. Too Early For Attitude
My daughter got into a relationship when she was barely in high school. This guy was already showing attitude problems. Anyone older than him was seen as an annoyance in his life, even at 15. He already started getting suspended in high school because of the same disrespect he would show toward his teachers and mentors.
He had unfortunately convinced our daughter to skip school a few times with him. Her grades started showing major drop and we had to start intervention. It took six months (and finding out that he had been trying to date two other girls) to finally stop the relationship. The worst part about the whole situation? He had gotten one of those girls pregnant by his ninth-grade year.
Seeing the relationship end, I felt a crisis was averted. A year later, as we were at home, our daughter came running into the living room saying he was outside her bedroom. Before I could check the backside of the house, a sheriff had come up to the house. The ex-boyfriend had apparently pushed his mom down a flight of stairs in an argument, took off, and thought to come here.
As I was talking to the authorities and telling my daughter to lock the doors, we heard the gate slam on the other side as he took off down the road. The authorities left in their car and we never saw him again.
13. A Real Winner
My mom was always super strict. She would follow me in her car when I wanted to walk just one block to a friend’s house in the eighth grade. Yet, for some reason, she was totally okay with 16-year-old me dating a 21-year-old bum. On the surface, he seemed trustworthy enough—but the truth about him would eventually hit me like a truck.
He never had any money—he would “borrow” some from me for gas, and he'd also complain about how his ex-girlfriend always wanted him to work. He thought she was nuts for thinking he should make his own living.
14. Big Yikes
My daughter’s boyfriend convinced her that if she stopped taking her meds, she wouldn't have epilepsy anymore. He said that it was only because she was taking mind-altering substances that she had a problem. Her condition caused a car accident, but she got out unscathed and no one else was hurt. She decided after the accident she would go back on her meds. Here's the kicker, though...
He dumped her because of it. She's now with an awesome guy who has Googled the heck out of "epilepsy," had long chats with me about what happens if or when she does have a seizure, and he is very much in love with her.
15. Divorce Is Sometimes A Great Choice
My sister-in-law is married to one of the worst people I have ever met. The guy is just completely awful. He’ll gaslight her and talk down to her so much that I just feel so sorry for her. However, whenever anyone slightly mentions his behavior to her, she’ll get really defensive. He refuses to spend time with her family as well; but when he is around, he's an absolute abomination.
He’ll pick fights and argue with her dad because he thinks it’s funny. He’ll also pick fights with strangers and when we ask why he does that, she’ll just say, “He can handle himself". I think because I’ve grown up with my sister and I have already dealt with her terrible boyfriends, this situation enraged me to my core.
16. It’s Not Too Late To Fix It
I used to be really close with my mom. When I moved, I would talk to her on the phone a few times a week. I liked being in touch with my family, even if it was mostly through email. But then I started dating someone who only saw the negatives in my family. The things he would say about them were appalling.
I didn't realize how consumed I was in the relationship, and I nearly completely stopped talking to my family for months. I was finally able to see them for Mother's Day, which was when I found out my mom really believed for some reason I didn't love her anymore. Hearing that just broke my heart.
17. All’s Well That Ends Well
Right after my daughter met her boyfriend, she started questioning all the things we drilled into her, like the importance of a college education and a good career. She thought (maybe because he was living this way) that she could be happy working retail the rest of her life making just enough to get by because wealth was "just material".
Eventually, she realized he was actually not stable because he had never had good benefits or a reliable paycheck. She also realized that he was just an immature fellow. It lit a fire under her. Before she met him, she was going through the motions, trying to find an easy path. Now she has set a goal for herself and powers through any obstacle. I probably ought to say thank you to the guy.
18. Who Knows What The Future Holds
About three years ago, my sister got married. Her husband is just a plain terrible person. He hates me (her brother) to my core, and he's even taken things from me, like my laptop which he tried to sell. Before my sister was committed to him, she was amazing. She always had a smile, she was bright, intelligent, and was working hard.
This guy works at a factory, swears constantly, screams, and yells at her, and I’m almost %100 sure that he's hit her. I wish she could just leave him, but there's one big problem—they just recently had a kid. A small baby that seems to be sucking the life out of her each and every day. Combined with him being there, I’ve never seen her smile.
I’m trying to be there for her. I still have hopes for her old self to return.
19. The Audacity
My first girlfriend took clothes from my mother and sister and wore them in their presence. She punched me whenever she got mad and one time, she even threw a skillet at me. She also cheated on me twice (I didn’t know about the first one until a few years after the breakup). But the most messed up thing she did? After a year apart, she came back to my life to tell me we should work things out.
I was about to fall for it until I found out she was married to some dude in another country. What was she thinking?
20. Delusions Of Grandeur
My nineteen-year-old sister is dating a 40-year-old man. The age difference is bad enough, but it gets even worse—he convinced her to pay for his truck and to drop out of college because he believes the only way you can get ahead is through working overtime in manual jobs. He once told me, a recent graduate in computer science, that there’s no money in the tech industry.
This guy takes care of lab rats for work and has no qualifications of any kind but describes himself as a historian of artillery, a computer scientist, and a sociologist. Before they got together, he lived with his grandmother...now my sister is paying most of the rent for their trailer. She’s extremely defensive about it so it’s hard to do anything.
21. Don’t Trust A Teenager’s Choices
I dated a guy who was 10 years older than me. He went through phases where he’d act as he adored me, and then he’d treat me like absolute garbage for months on end. The reason he gave me for his unacceptable behavior was disturbing—he said it was because he had multiple personalities. He’d break my things, punch holes in walls, and scream at me about nothing for hours on end.
My 19-year-old brain thought I loved him. But he completely isolated me from my parents, and I didn’t speak to them for about a year. Mind you, I had always been really close to my parents growing up and I had just moved out. This guy even convinced me to be homeless with him for months, then made me use my money to get us a place and he lived there rent-free.
He refused to get a job. His goal in life was to have a baby with me, and he didn’t tell me until later that he had two kids with two other women that were taken away. Luckily, I left him after two miserable years, and everything is okay between me and my parents now!
22. A Whole Mess Of Red Flags
My dad and my college advisor both hated this one guy I dated because of how he spoke for me. They’d ask me a question, and he would answer. But his mother was even worse. When I went to meet his family for the first time, I made the most glorious Martha Stewart-level pie, except he never told me his parents kept kosher.
She threw the whole thing, dish and all, into the trash without so much as a word, and spent the entire weekend speaking exclusively in Hebrew. The woman speaks perfect English. I knew some of the words, and a friend of mine had also told me about some of the bad words before; namely the ones for derogatory words for women.
She called me all of them thinking I didn’t understand. The guy didn’t care that his mom hated me for no reason; he just didn’t think it was a big deal. He and his father spent the whole weekend at each other’s throats—evidently, this was their usual dynamic. Also, he didn’t know how to change a tire. I had to do it one time when he blew his out hitting a curb—a mistake on my part that I would end up paying the price for.
He complained the whole time about how I emasculated him when I did it. When we first met, on one of our first dates, he “accidentally” threw his car keys into the sea. I kid you not. Looking back, I think he was likely being dramatic and making sure our date went on endlessly. We had to walk like three miles in the cold back to my apartment.
23. You’re Only Young Once
My daughter dated this boy throughout high school and they did everything together. He deprived her of the normal high school experience of having friends, going to parties, making mistakes; all that memorable stuff. She made the choice despite me and my wife raising our concerns. We tried to get her to experience what being young can offer, but he got in the way.
Anyway, long story short, he lost her trust when he crossed the line...BIG time. He cheated on her days before her graduation and left her alone with no date to the prom. She was too heartbroken to even enjoy one of the milestones of life! She put on a fake smile for pictures but we both clearly knew she did not want to be there. She was so excited that she even planned for months for this day. My heart was broken for her.
24. She Was Not The One
My daughter had the misfortune of dating a very angry woman with a fervent dislike of men. She was the most unpleasant person I've ever had the misfortune of meeting. She not only tried to turn my daughter against me but also against her brothers. Given that we are a close family, we were absolutely devastated by this behavior. She thought she was in full control, but my daughter would end up having the last laugh.
My daughter eventually saw the light and dumped her. The woman she's now married to is like another daughter to me and they are extremely happy together.
25. Father Knows Best
I had a boyfriend named John that my dad despised. He thought John was hindering me from a promising future. He was a delinquent with no prospects as far as my dad was concerned, but my dad's hatred of the guy made me want to be with him more to prove my dad wrong. Unfortunately, my father wasn't wrong.
John and I ran away to be together, and the reality was so much worse than what my dad thought. John was an insecure manipulator who spent all my money and did a lot of substances. We broke up, and even to this day, my father doesn't know half of it. Though any time I've messed up or something goes wrong in my life he says, "Well, at least you didn't end up with John".
26. Hopefully, Things Change
Before she met this guy, my sister was the nicest person ever. She would help anyone out and not expect anything in return. However, this guy was a massive control freak—he would do stuff like check her phone without her permission, make sure she was at work and not off with friends, stuff like that. For some reason, my sister didn’t think any of this was bad. But then she moved in with him, and she started to spiral.
She became really mean, demanding money from my mom and getting angry at my brother when he would say bad things about her boyfriend. She was even telling her longtime friends to leave her alone. All we could do was stay out of it and hope she would eventually leave him. At the moment, she's still with him and the situation just really sucks.
27. They Were Just Kids
My son is a deeply compassionate and empathetic person. His first girlfriend took advantage of this. They were 16 and she would just sit around all day, every day. She had no drive or ambition. She was mentally unstable and controlling. He could not be around any other girls ever, even his female best friends, or she would scream and yell and cry.
He was an honor student, a popular kid at school, a student government member, and a class officer. She dragged him down with her emotional neediness and influence. He chose to do some bad things—not saying it was all her, but it took him four years to get away from her. When she left him, he lost it—he descended further into depression and substance use after they broke up.
He has finally come out of it, but the whole experience has scarred his soul and left him with lasting memory loss as well. He now sees her for what she is and I am always thankful he never got her pregnant.
28. He Was Busy
One particular student transferred back to the school I teach at because of certain trouble he was getting into. Within the span of a year or two, he dated at least three different girls and messed them all up emotionally. I know this because as an English teacher, students tend to write about some of the worst moments of their life.
Little did those girls know that they all wrote about the same guy! Two of them actually said his name in their papers, which I might still have around somewhere. Anyway, the first girl talked about how they became such good friends. He told her he loved her so they tried dating, and then he broke up with her to chase the second girl.
The same thing happened to the second girl when the third girl came along. From the moment he saw him, her dad knew this kid was trouble. He forbade her from seeing him, so naturally, she’d have him sneak in through her window (all mentioned in her paper by the way). One day, he persuaded her to ditch her parents' house and they spent a night out in some low-key hiking park.
The authorities were called and they were eventually located. He broke up with her two weeks after that for supposedly another girl. I had this guy as a student and as a player on the soccer team. He’s definitely a gifted charmer—he uses a sense of false humility to lure people onto his side.
29. Don’t Date Musicians
My sister has an amazing sense of humor, but one guy she dated would get angry whenever she made jokes because “he was the funny one". She was finishing up her degree and he was trying to make it as a psychedelic rock musician. She had to support him financially, so she was at all his gigs...and she even carried his gear for him.
He never took any interest in her life. I remember he got angry at her for asking him to come to her graduation. Then, another time, he was browsing Instagram and she asked him whether or not he was listening to her. He put his phone down and gave a chilling response: “Do you see how important you are to me, I'm putting my phone down for you. That's a big deal".
He acted like he deserved a medal for paying attention to her. He was an annoying narcissist who thought he was a hotshot because he played a gig here and there. Finally, he threatened to hurt himself if she left him, but she did it anyway. Now, he's a bartender who never made it as a musician and she's with a thoughtful guy who supports and loves her.
30. This Is Too Much
One of my sister’s boyfriends in high school was 21 and his entire life revolved around his mom. He didn't even have any of his paperwork (his birth certificate, SSN card, etc.) because his mom refused to give it to him. He stayed home all the time and took care of his mom and younger siblings. Despite this, my sister spent four years of her life on him...until one day, she had enough.
My sister always had firm boundaries regarding her boyfriends, but when it came to her boyfriend's mom, she didn't know what to do. The guy was okay but he was too attached to his mom and he wasn't going anywhere in life. I'm just glad my sister saw that and left him.
31. Never Get Involved With A Fixer Upper
My younger sister has always been a very impressionable person. She's the type to give in to peer pressure because "everyone else is doing it". This was not just when it came to boyfriends, but regular friends as well. All of the guys she dated in high school were all losers and basically going nowhere in life.
This had a very negative impact on her entire life. She would often sneak out on school nights to hang out with them and lie to our parents about where she was. I feel like part of the reason she attracted these types of guys was because she was insecure with herself; as if her self-worth depended on being in a relationship.
She seemed to think that she could fix them somehow. She didn't and they basically dragged her down. Fortunately, she eventually smartened up and realized she deserved better. She got her act together and is currently dating a very nice guy who treats her well and is the kind of influence that she needs.
32. It Was Nice While It Lasted
My brother dated this girl who was clingy and would insist on him staying over at her house multiple nights in a row. Her mom took a liking to him, to the point where she would drive him to school and buy gifts for him regularly. Whenever he had second thoughts, her mom would convince him to stick around a little longer.
It was a weird relationship that put a strain on him and my mother, and eventually, he moved in with her. That's when things got really, really weird. The mother started to obsess over my brother, and it became clear to us that she was living vicariously through her daughter's relationship with him. My mom finally put her foot down and told him to either come home or deal with having the locks changed on him.
He decided he had it made over at his girlfriend's place, so my mom locked his room up while his girlfriend's mom was having a field day buying him clothes and gifts. It drove me crazy watching her luring him in like some kind of spider, while my mom was a virtual wreck about losing her son to some stranger who thought she knew him.
This lasted for about six months until finally, my brother got tired of being smothered by both his girlfriend and her mother. He broke it off abruptly, and my mom joyously took him back. Through all this though, my brother has lost a lot of respect for my mom because he thinks she overreacted about the whole situation. He still acts entitled from time to time, and I don't feel nearly as close to him as I used to.
33. A Delayed Ending
When I was younger, I dated a bloke named John for a while. Even at the tender age of 18 years old, I was his sugar momma and I financially supported him. By the time I got older, the shine was off the relationship and I was emotionally checked out, but I also had a fancy new job in my near future after a few months of minimally-paid training. So, I reevaluated my life and had a big decision to make.
I was procrastinating the official breakup until I was through this training phase. I wanted to still be able to store my stuff at our shared apartment until I got a real paycheck coming in.
34. Not A Good Enough Reason
My sister is dating a pretty bad guy right now. Their romance began with scandal. At that time, this guy was dating another girl, so my sister voluntarily took the role of mistress. This went on for about a month, after which he said, "Girls, maybe we'll meet the three of us?" Fortunately, my sister was not satisfied with this arrangement, but she did not consider it a red flag. She would soon live to regret that mistake.
When I asked, "What binds you? Why do you keep dating him?" She replied, "He has the same terrible mother as ours. This is the only man who is able to understand the extent of my pain".
35. Crystal Healing
I dated someone who was deeply involved in spiritualism. I didn't know it at the time, but I'd eventually learn the hard way that this was a huge red flag. Her mom paid her numerologist to tell her that if she legally changed her name to one that suited her better, her soul would improve. They spent years paying a "therapist" to tell them about fractal reality until word got out about how many patients he was grooming.
My girlfriend kept trying to get me involved in seminars and magical oil businesses. I got out of there pretty quickly and never went back.
36. A Rebellious Few Years
My niece’s first boyfriend got her strung out and she dropped out of school. Her mom was a complete pushover and my niece would just have her friends over while her mom worked. Not long after the start of the relationship, my niece moved down to Florida and her boyfriend ended up being locked up for one thing or another.
When he got out, they get back together, and then no one in the family heard from her in almost two years. When we finally got a call, we assumed the worst—but she was actually calling to ask someone to come get her.
37. The Effects Of Time
My daughter’s boyfriend just broke up with her two weeks ago. He was perfect for her at first. He had less money growing up and claimed to never get presents on his birthday or for Christmas. We would always give him something special so he felt loved. Well, as the years went by, he started trying to control who my daughter talked to and hung out with.
That was bad enough, but he took his tyrannical behavior to another level. He got it in his head that she was going to leave him for a woman because she cut her hair short. He also wouldn’t talk to her or acknowledge her if she did something that he deemed wrong (like not letting him cuddle her when she was eating). So fast forward to a few weeks ago—he had begged to come over after school even though my daughter wasn’t feeling well.
He spent time with us, even though she was mostly in the bathroom. As soon as he got home that night, he texted her to break up. He claimed that she was too immature for him, and he even went as far as to say that he hopes she can find someone who can put up with her nonsense.
38. Over Before It Started
My daughter dated an awful guy. He’s my age and married. He has seven kids with five different moms. Yes, one of them is my grandson. He convinced her to give him every dime she had and played wicked mind games with her until she really couldn’t tell what was real and what wasn’t. Then he took off and moved three states away. And the cherry on top of it all—he’s never paid a dime of child support.
39. What’s Yours Is Mine
My best friend has had a few awful relationships, but the worst one was when he dated a kleptomaniac. Now, my friend and I run a tech repair service as a sideline, so there are some fixed gadgets lying around in our workroom, mostly the ones the owner sent to repair but couldn't be paid for at the current moment.
Enter his ex-girlfriend—she seemed harmless until she crossed the line and showed us her true colors. It all came to a head when she "borrowed" one of the iPads. A week later, we found out that she ran away from home, and sold the gadget she "borrowed" to pay for a motel. Anyway, after that, they broke up.
40. That Poor Girl
My daughter got pregnant by a high school dropout with a sealed juvenile record. The guy had a disdain for any authority figure, as well as a slew of anger management issues. She eventually gave birth to my granddaughter, who is the sweetest little girl—but her deadbeat boyfriend doesn't help out at all. The one thing that gets my blood boiling about him is the fact that he has never had a job, yet she’s still with him. He and I don’t get along whatsoever.
I help from a distance since my daughter has problems of her own that she refuses to take care of. If I was 10 years younger, I’d probably sue for custody of my granddaughter to get her out of that situation.
41. She Can Do Better
I dated a guy for about 18 months and he remains to be one of the worst people I've ever met. He was very manipulative with attitude problems, and he was constantly in trouble at school for harassing a lot of guys. When we broke up, he bullied me mercilessly. Upon discovering that one of his friends had a crush on me, he reacted in the pettiest way—he would walk past him and whisper stuff like "traitor".
He always acts like he's the victim of everything, and he gets mad when he doesn't get his way. He also pretends to know everything about everyone. While we were dating, my relationship with my family, especially my dad, broke down, my grades slipped, and I completely changed as a person.
42. He’s Hooked
My brother started chatting with a girl some years ago. Nothing too out of the norm at first, but he started spending more and more time with her in calls, usually eight to 10 hours a day on average. And he was supposed to be completing high school at the time. This guy had been spending every waking moment out of school in a call with her.
As a result, he started sleeping constantly in school, almost failing three years in a row. Needless to say he was borderline obsessed with her, but thankfully she ghosted him and things returned to normal. Two years later, my brother and I were about to enter college as freshmen and we were caught completely off-guard—out of nowhere, she decided to start messaging him again.
He suddenly went back to spending all his time with her, dropping his college responsibilities to give her the time she wants. Apparently, the reason she initially ghosted him was that another dude she was seeing at the time had her block everyone she knew on online messaging services, and she did so willingly.
But now that everything was fine in her life, she decided that she would like to keep spending all of her time with my brother. Over the course of this relationship, she had convinced my brother to make different plans for their relationship in the long term that involved him spending his very limited amount of savings on a plane trip. But that's not even the worst part.
She also convinced him to enter a polyamorous relationship with her then-boyfriend so she could have both of them as sugar daddies, as she has previously stated that she wishes to be taken care of and does not wish to work for herself. This man has suddenly changed his college plans to move to her state as soon as he could afford another plane ticket.
The amount of time and opportunities he spent on her makes me mad, and I am genuinely worried he may never rid himself of her. This man has been my brother for 18 years, but whenever she's around, he becomes a totally different person.
43. A Confession
I was an awful person. I cheated on my girlfriend less than two weeks into the relationship, I didn’t tell her about it, and I lied to her consistently throughout the relationship, including about the cheating. There’d be stretches where I just wouldn’t communicate with her at all. I was on Tinder at points throughout our relationship until one day, her best friend saw me. That's when things turned upside-down for me.
I took a girl who deserved nothing but love and respect and I treated her like she was nothing. The one-year anniversary of our breakup is coming up—I just hope she’s healed from all the damage I did and is able to move on to a guy who will do what I should have.
44. A Happy Ending
When I was 14, I dated a kid from another state over who was 16. I never met him but he was obsessed with me...so obsessed that he would tell me to block my guy friends and tell me which colors I could and couldn’t dye my hair (I had pink highlights in at the time). I always had to be on the phone with him, even if he was sleeping. These were bad enough, but the real red flag was yet to come.
He would force me to say things I didn’t mean. If I was on the phone with someone else he would make me get off the phone just so he can play video games with me. We had our fun times once in a while but I ended up breaking up with him.
45. A Tough Time
My sister dated a guy who drastically changed her. A lot of this can be attributed to the substances that he turned her on to, but the changes were still incredibly dramatic. She went from being a normal young girl to an absolute wreck. She would throw things and rage at my parents. It was one of the hardest times for both me and my family.
It wasn't until years later that she was able to shake him, and then shake the substances. She has been sober for almost a year and a half now, and I am so thankful to have my sister back. Still, there are some lasting effects that you can see in her psyche, such as her inability to trust and her quick temper. I'm just upset that she had to go through all that.
46. Mistakes Were Made
My mother has never had anything against gay people, but when my sister came out, she got super upset and kept urging my sister to change her mind. My sister had been talking a girl online who was six years older than her, and one morning, she decided to tell my mom that she had a girlfriend.
She once lied to my parents and said she was going to hang out with her friends, but instead, she drove an hour away to see her girlfriend. The next time she drove out to see her, she had already told my parents about her, but my mom was begging her not to go. Well, she did anyway. I usually take my sister's side when she gets into an argument with my mom, but this time I actually felt bad for my mom.
I wouldn't want my daughter driving to see some older person she met online. Anyway, it all went downhill from there—the girl was the extremely jealous type, so she forbade my sister from doing things with her own family. For example, she wasn't allowed to get dinner or to even go out for a family member's birthday.
She has been living with this girl and her mom for about a month now. She's changed a lot and only cares for her girlfriend now. She used to be a great sister, but now I feel like I'm an only child.
47. That Was Short-Lived
My daughter met her first boyfriend during her last year of high school. She’s a tomboy and loves to play sports. He was a soft-hearted poetry writer and always discussed the meaning of life. I knew it wouldn't last, but it also wasn’t harmful, so I didn't say anything. She went away to school and they vowed they would be together forever...until she discovered his big secret that he'd been hiding from her all along.
Six weeks later she came home for Thanksgiving and found out he had cheated so she dumped him.
48. What A Mess
I met my very first boyfriend at a church retreat when I was 16 and he was 17. He convinced me to lie to my parents multiple times. About four months in, I went down to visit him (he lived in a different state) and we went out to a mall with his friends. At one point, he wanted to kiss me, but I said no. His next move made my blood boil. He put me in a chokehold, in public. His friends did nothing.
While down there, I met one of his friends, a girl, and we got close. My boyfriend decided to tell her I was bi and that I had a crush on her girlfriend. I didn’t. She then blocked me and I was never allowed to talk to either of them ever again. Fast forward a month later—I had enough of his scheming ways and I told him we needed to take a break.
He agreed. I later came back to him and found out that he had lost his virginity to the girl who cut me off.
49. Bad Choices Were Made
My sister once dated one of the higher-ups of the brotherhood years ago. She originally showed up with some new boyfriend who was this massively tatted guy and she acted like it was all fine. She wouldn't believe me until I showed her a website that revealed his dark truth—it cataloged the common meaning of some of his more unfortunate tattoos.
He didn't have anything super blatant, but he had lots of the other ones that indicated he was a part of a dangerous gang. Eventually, he told her all about his extensive time behind bars, why he went away, and what he did while he was there. My sister is smart, but she has absolutely zero common sense and potentially negative street smarts.
50. Good Timing
My daughter was preparing to move in with her boyfriend. The boyfriend left his laptop out, and my daughter used it for a quick Google search. What she found on it shook her to her core—his search history included things like "How do I make my girlfriend submissive?" and "How do I make my girlfriend do whatever I want?" They broke up that day.