Everyone knows someone who's dated a loser, but when it's a close family member it can be incredibly difficult to get them to see the light at the end of the tunnel. These Reddit users have WORDS to share about their family member's loser exes.
Content has been edited for clarity.
They’ve Tried Everything
“My wife and I have very limited contact with our daughter because of the guy she was dating and now ended up marrying. Our ability to intercede was limited because she had moved to the other side of the country, ultimately ending up in Alabama. It’s painful and incredibly unfortunate, but we are just holding out hope that someday things turn around and she opens her eyes.
Our daughter was staying with a friend, and she began dating this guy she met while working. She always struggled with showing or expressing gratitude, and she had a falling out with her friend of 10 years, who felt like she was being taken advantage of. Our daughter wouldn’t pay rent and did nothing to help out around the house (friend had a new marriage and a new baby also) and so our daughter was asked to leave. She lived with her manager, until they also had a falling out, resulting in her quitting her job also.
This caused her to move in with her boyfriend, who we’ll call Tim. Tim lived in a trailer on the same plot of land his parents and grandparents lived on, and was likely a dealer. He had been in the Army for a few years before getting dishonorably discharged for substance use. Given that my wife and I are both Army veterans, his ‘I’m a proud Veteran’ attitude was additional reason to dislike him. He had no real job, which would be a trend.
They ultimately got engaged once our daughter became pregnant. We were then contacted by a woman who wanted to warn us about Tim. Turns out, she was his wife. They had been married years earlier, had a kid together, and Tim was refusing the sign the divorce papers. She informed us that he was emotionally and physically abusive, and that he had been convicted of it (we checked and this was true). He was also currently on trial for assault (was also true). She also claimed he was currently sleeping with his 15-year-old cousin who lived in one of the trailers on the family lot (no evidence other than circumstantial ‘he’s a piece of work’ evidence).
My wife immediately called our daughter to tell her this and to try to let her let us buy her a plane ticket back to our house so she could get back on her feet. Turns out, our daughter knew about all of it and refused to believe any of it was true. He wasn’t dishonorably discharged she said (we sent the picture of the DD214 his wife had), he wasn’t an abuser (we sent the court case and local news article), he was on trial, but there was no way he had violated anyone (case was ultimately dismissed last year when the witness decided they didn’t want to testify). She said she’d come for a visit, but only if she was allowed to bring Tim. We showed her texts from Tim to his wife saying he was only with our daughter for the money (she had been begging money off relatives, though we had stopped giving at that time, and all have stopped now after we talked to them). We also showed her his tinder and Facebook profiles where he was attempting to pick up other woman. Nothing made a difference.
She had the baby a few months later. We were going to go out for the birth, but we told our daughter we wouldn’t go onto their family trailer park. Tim knew what we thought of him now and apparently made threats toward us. We told her we’d come out and stay in a hotel, and we could visit her there. She refused and said Tim wouldn’t let her do that. If we wanted to see our grandchild, it would have to be at their trailer. We decided not to go out for the birth, which tore my wife apart. Our other daughter has not spoken to her sister since that day.
Everything seemingly came to a head when our daughter called us out of the blue one afternoon. Apparently Tim had gotten angry and she was scared for her safety. We immediately booked a flight for her and our daughter arranged for a neighbor to take her and the new baby to the airport. We then could not get a hold of her for several hours, so my wife called the local police to do a health and welfare inspection. The officer had our daughter call us from his phone. Apparently, he had found out what was happening and smashed her phones and would not let her leave. The neighbor now refused to be involved, so a former soldier of my wife’s offered to drive out and pick her up, as he happened to be a police officer about two hours away. The other officer waited for him to arrive. Once our friend arrived, our daughter had changed her mind and refused to leave. Nothing we could do changed her mind, and she is still there.
Tim still doesn’t have a job, though they are now married and she just gave birth to another grandchild. Tim insisted that she go back to work the week after, since he cannot get a job due to his record. Our daughter sends us pictures, but she is always sure that they include Tim. The last picture we received was him holding the new baby and making something in the kitchen… while smoking.”
She Got Out Fast
“At 15 I started dating an 18-year-old boy named Jon. He and his even worse mom lived in someone’s hallway.
That’s right. The two of them, on a twin mattress, in a hallway. Together.
They both refused to get jobs, but he did have a throw away phone. Since I was 15 I wanted to text/call him so I paid to put minutes on his phone every week. With my LUNCH money. Yeah.
We went boating with my grandparents and he tried to do it with me on their boat. It was a fishing boat, and only about 10 feet long. So he tried to get it on within 10 feet of my grandparents and baby brother, in their line of sight.
We went to a sporting event for my baby brother and he made me go outside and tried to do it with me on a public picnic table.
He would beg me for money to feed him and his mother.
Then, when I tried to break up with him he told me no. He wasn’t allowing the break up. I told him I was serious, and then behaved as if we were broken up anyway. So when I moved on he told everyone I cheated on him, then stalked my new boyfriend. Once he realized it was actually over he and his mom called me nonstop one night saying they wanted his hoodie back. I said I would bring it to them the next day, but that wasn’t good enough. They needed it right then. So they said they were going to come to my house and get it, at 3am. I told them no. And he and his mom left a voicemail on my phone saying they were on their way and were going to beat me up over stealing this hoodie. I was a minor, he was 18, and she was over 40.
So I called the cops.”
A Messy Prom For Sure
“My son dated a girl who said she had a friend who needed a ride to the prom. I agreed. Day of the prom, she says ‘oh, he’s in this town… in the next state.’ I left work at 10AM, drove three hours, picked up this kid, brought him home. The reason I was willing to pick the other kid up was that he was a different girl’s prom date. He has no prom clothes. Not even a suit. Luckily, we’re close enough size-wise that I can lend him one.
I lend him suit, shirt, tie. Buy him dress shoes. Pay for haircut. We’re late, so the pre-prom dinner my kid had planned is out the window. Pictures not possible because we don’t have time. We get one decent snap. Guess who’s in the center? Yep. Out-of-state-dude.
Girlfriend ended up spending the entire prom with this dude. Apparently he was an ex. They go to an after-party. My son is left behind. He gets his own ride home, but doesn’t stop by to drop off my suit & tie.
Later, we find out: girlfriend and out-of-state-dude had baby-making session at some point during that night. Baby was formed.
Who is the father? According to girlfriend, my son is. Complication: they never have been intimate, according to him. She would have gotten away with it to some degree but had the bad judgement to tell friends that it was actually out-of-state-dude. Fortunately, my son found out and broke it off with her.
To be honest, I could have written all that off as youthful idiocy. But a few months into the pregnancy, she has the balls to come to our house and tell me that her parents were kicking her out- and would it be OK if she moved into my finished basement apartment so her baby wouldn’t be homeless? Like WHAT?
The end of the story is that out-of-state-dude heard that he was the baby-daddy and came back to bring her home with him. And as far as I know, they are still living in his parents’ trailer.”
Bad Judgement Runs In The Family
“This is about my sister’s boyfriend and my own.
So my sister decided to date this malnourished street rat within her emo circle. Everything was pretty fine from the looks of it until she started hurting herself. Eventually my family and I found out that he was cheating with girls left and right. (I find out from one of my more active friends. She didn’t know about my sister and basically said he manipulated her into hooking up with him under the bleachers.) What’s worse is that my sister knew everything, but was too insecure to leave him. I and even everyone in the school did our best to convince her to let him go. It took her a good 3 years, but I was just happy she finally did it.
My own personal one would be when I was in HS and asked out a guy that interested me in P.E. He seemed pretty goofy and nerdy which was definitely my type so I thought why not? It was honestly pretty badly planned, but yes… I asked him out in PE in our stupid PE uniforms. Anyways he said yes. After PE we walked out of the locker rooms and he was waiting for me. He checked me out and said, ‘wow they’re a lot bigger than I expected.’ And walked with me nonchalantly. I was so baffled I didn’t even know what to say. What was worse is we only really hung out IN PUBLIC and he’d tickle me then slowly creep up to grab my chest. I would tighten my arms to my sides so he couldn’t but kept nudging anyways. It made me extremely uncomfortable. And don’t get me started on the hugs. Literally on the third day I broke up with him. It felt great to not worry about someone groping me in my school.”
She’s One Crazy Lady
“My brothers now soon to be ex-wife. Started dating when he was 15 and she was 14. There were so many red flags we should have seen initially but just didn’t. She hated any girl that was remotely nice to him. She was jealous and would start fights over the fact he had previously dated other girls. Would not allow him to attend his debutante as she wasn’t in his year level and would have to dance with another girl (she did hers with a guy my brother hated with a passion). Was always just nasty to him, never really nice, play fighting was just a little too aggressive. She was always generally nice to me and our family and we were nice back. Mum purchased her university books, let her live with us for nothing when she decided she didn’t like her family. She then decided one day to just move out, cut all contact with us for about 6 months for no good reason. Couldn’t even give my brother a reason.
Then in the spirit of Christmas, my dad extends the olive branch and says that he wants to work things out for the sake of my brother. So everything is forgiven and she moves back in. She and my brother purchase land and everything is going smoothly except for me standing up for myself as I don’t want to be bullied by her or allow her to treat my brother/family like crud.
So one day out of the blue she blocked me on all social media, Facebook, Snapchat even blocked my number I figured out when I tried to message and confront her about it. She went two weeks in my house avoiding me and would not respond to me if I tried to approach her about it. So then one day my dad asks her to move her car as she’s blocked him in and he needs to leave. She grabbed her things, stormed down the hall, slammed the door shut, got in her car and sped off. I never saw her again. My brother moved out with her to ‘preserve the relationship’ between all parties involved. Then over Facebook we find out through a relative (been blocked by both SIL & brother) that wedding invites have gone out. So none of my brothers family attended his wedding.
We still had an okayish relationship with my brother and were cut but respected the decision that clearly wasn’t his. They build a house and live together for a while. At this point he’s been planning to leave her for 6 months. He snuck away to celebrate my mum’s 50th with the family and admitted he’d been sleeping in his car to avoid her and had to fabricate emails as an excuse to leave the house to celebrate with his family. Then we come to the night he finally decided to leave her. He was out doing volunteer work he loves, they have plans to do something in the evening but he’s about 1 hour late, still able to go do what they planned. NOPE, she absolutely loses it. She begins to smash his MacBook on the kitchen counter. He told her that he’s done and he’s leaving her. Go’s to get his bags which he had packed and hidden and to pack the rest of his crud. When he goes to leave, she grabs his hand, bends his fingers back with intent to break them.
He’s now back home with us, safe and happy. I hope she rots.”
This Guy Might Be The Worst
“Best friend has always had self-worth issues. She is really smart and gorgeous. When she came back from studying abroad in Germany, they met. He was your typical substance using prick. He lived with his ex-gf. Convinced her to let him move into her mom’s place with her and her siblings. Constantly threatened that he’d break up whenever she went out without him. Like she came over and we mostly just talked, but he was convinced that she was cheating. So he came over, and complained every time that he was bored. But if he left, he blew up her phone and called her a fat cheating loose woman more times than I care to count. He convinced her that I, the only friend who tried to stay with her (knew the guy was a manipulative tool but she wouldn’t leave), was toxic and I was phased out. I keep inviting her to things. No response. Her mom invites me over to celebrate her birthday. I go, and when I arrive the house is destroyed. Like chair through the front window, holes in the wall, brother (8) and sister (7) are hiding, and mom is nowhere to be found. Turns out boyfriend lost it when my friend came out of their room wearing the outfit I bought her for her birthday. (She had lost a lot of weight intentionally, but boyfriend said she couldn’t waste her money on clothes because it promoted her loose lifestyle.)
She wouldn’t break up with him. They got kicked out of her mom’s house, and moved into her dad’s one-bedroom apartment. They took the bedroom. I am not allowed to have contact with her. I came over to bring Christmas cookies to her dad (I kept him company when she was abroad and spent Christmases with him). She and boyfriend are at work. I find out that boyfriend broke her phone. Literally smashed it. Friend wouldn’t listen to her dad, but he didn’t want to kick them out bc dad stopped the physical violence on more than one occasion. He was scared she’d be murdered. Boyfriend came home and had a nuclear meltdown when he saw me. Dumped my friend, and left this super long message about how she was a dumb fat loose woman and would never amount to anything.
They get back together. I see her on social media. She is getting thinner and thinner. Things finally changed after her dad had surgery and was too weak to fight boyfriend off. She left him when boyfriend sent dad to the ICU.
But, he has showed up multiple times. Threatened to kill her and her dog. I just hate him.”
Some Guys Are Truly Monsters
“My daughter’s ex-husband, the cop. Who broke into her house after the divorce and violated her in front of the children. Thankfully the maggot did time in prison for that.
The full story – my father had a massive brain aneurysm. They had taken him to a hospital 5 hours away. I had just arrived there when my ex-husband called me and said my daughter was on the way to the hospital and told me what had happened. It was definitely non consensual, from someone who asked was it really or did she just say that when the children saw them. There was no question due to the trauma. He stands 6’4″, my daughter is 4’11” and weighs 100 pounds.
The kicker was that we found out he had a bit of a history of being a predator, as he was one of those cops that would solicit favors when he stopped women, i.e. they could get out of a ticket… if…. The department he worked for got wind of this and they reached some agreement whereas he would quietly retire and nothing would be on his record. I can’t remember exactly how my daughter found this out, but I know it was shortly before the trial and someone came to her about it.
So yes, he did time. He is now out. There is a restraining order in effect for 7 years, and most likely that will easily be renewed. He has taken her to court I don’t know how many times in the last couple of years, trying to get the restraining order lifted because he states it is keeping him from gaining employment, since it’s attached to an assault. He represents himself every time he comes to court, it’s almost comical. He’s narcissistic and psychotic. I call him stupid maggot.
The kids were all in therapy. They’re great kids, very well-adjusted. She’s an amazing gal. She’s 3 months from her masters, works full time, and has never missed one of the kids’ activities. They dealt with it and moved on. To quote Shakespeare – ‘Though she be but little, she is fierce’.”
He Had Too Much Power
“My little sister did ballet from about 5-20 years old, from about 12-14 years old one of her instructors was Jared (The Dirtbag). Let me start by off by say The Dirtbag was not a Pedo, he and my sister started dating when she was 20 and was now teaching ballet at the same school as The Dirtbag, who was 34 at the time. The fact he was older and had a position of power bothered me, but it wasn’t until we started hanging out more that it became clear just what a controlling, manipulative dirtbag he really was.
My sister is a personal trainer and going to college to become dietitian, she volunteers at The ‘Y’ to teach 4 and 5 years old ballet and also a senior citizen exercise class, she’s in great shape, but one of the reasons she stopped doing ballet was because she did not have a ballerinas body and never would. The Dirtbag was constantly making comments about what she ate and her weight, the amount of exercise she was doing, drinking too much, and staying out late even if it was only hanging out with family. He was clingy and naggy. Thankfully my sister is pretty independent and eventually (after like 2 years) got tired of him always being around and dumped his butt. He’s the only boyfriend of my 2 sister’s I’ve ever really wanted to pound into the ground, it hurt even more because I stopped hanging with her because I was such a prick to him.
She’s had others that were bad, but he was the worst.”
They Gotta Break Up, Right?
“My sister has been in a relationship with her boyfriend for 5 years. They started dating when they were 17/16 and it was a normal teenage relationship, they partied together, went on dates, etc. This boyfriend is my best friend’s brother, so I have known him since I was 5. I love his family, but his parents were never involved with him (i.e didn’t care if he went to school, never asked where he was). I guess I understand where he went wrong, but I have no sympathy for how stupid he is.
It was all fine until 2 years ago, he moved with my sister when she left for a new college. Of course, he followed her. All he had to do was work and pay their rent while she was in college so she could focus on her studies, and he agreed. 10 months later, my sister breaks down and we find out he has not paid one dollar for rent, let alone food. He constantly blows money on dumb cars just to have a new one every few months. He could not hold a job and relied on my sister for all the finances. Not only did he use her, they ran through 85% of her savings money she had worked hard 3 years earning. Around $7,000. She kicked him out.
They are still dating, which is the biggest mystery to me, my sister keeps giving him chances. My family won’t allow him around anymore. She just moved back to college after the summer without him. I am hoping she slowly loses feelings.”
She Almost Lived In A Garage
“My little sister dated a guy who kept trying to convince her to drop out of a UC school and move into his mom’s garage with him, up to and including threatening suicide if she didn’t.
It took way too much effort on my dad and my part to get her to put the kibosh on that relationship, mostly because the guy’s mom thought my sister was good for him and tried to fight us on it.”