16 People Describe The Biggest Psychos And Losers Their Family Members Have Dated

We’ve all likely dated some unsavory characters. But dating a person who is kind of a loser and dating one who is a total batsh*t insane psycho of a loser are two very different things.

When Reddit user u/eternalsoul116 posed the question, “Who’s the biggest loser your son/daughter has dated?”, the AskReddit community responded in full, though the majority of responses weren’t from parents, but from siblings, friends, and other family members. Read on if you dare…

16. Threatening suicide if their partner leaves:

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.

15. Doing this:

My husband’s cousin was married to a man who cheated on her for months, and then moved his mistress into THEIR home and tried to convince his wife that they could all be lovers together.

He also got into the illegal pot dealing game after Colorado legalized weed.

14. Having not one, but two swastika tattoos:

My sister is married to a guy who has two swastikas tattooed on his back… nuff said. Edit: He got them while in prison when he joined the aryan brotherhood. He definitely isn’t Buddhist.

13. Every single one!?

Obligatory “not a son or daughter” scenario, but my older brother dated a girl who pretended that she broke all of her bones in a car wreck.

She put both of her arms in slings, put braces on her legs, and a travel pillow around her neck. I remember asking her about her back (if all of her bones were broken anyway) and she started to cry.

LOL they didn’t last long.

12. Being really, really irresponsible with money:

My sister dated a guy, lets call him Tom, who worked under my dad at the business he owns and runs. Now I’m not saying Tom was a loser because worked for our family, my sister and I both work in similar positions and thats how they met. But there were a number of instances that just shouted ” Hey whats up I’m Tom and I’m a loser.”

For example, Tom seemed to never have any money, usually blaming things like his rent being to high or his car needing to be worked on. Due to this my sister ended up having to pay for the majority of the dates and dinners that they went on.

In reality, he had spent most of his money on unnecessary toys like Dirt bikes, guns, and modifications for his 1999 Honda civic. His spending habits got so bad that his landlord threatened him with eviction, this tore my sister up, not because he was getting evicted but because she knew that he was making enough money to never be in that type of situation.

Anyway, Tom got the bright idea to ask her and my father for the rent money ($650) while they were out to dinner. My dad ended up helping him out so he wouldn’t go homeless, but what he didn’t know was that Tom had asked him for more money than what his rent was so he could go out and spend it on other things other than my sister.

So yeah he was a loser and I didn’t like him much.

11. Or just straight up stealing it:

My sister dated them all! My favorite was a guy who convinced her to have joint bank accounts and stole 6 months worth of pay from her.

We didn’t know until after the relationship. The dude was a major conman salesman type that had like 4 different get rich quick schemes while they dated.

10. Being a dangerous enabler:

My sister is dating a guy who is a asshole to everyone he meets, but cries when you give it right back to him. He is also an enabler to her depression and anxiety. Instead of trying to encourage her to fix herself, he tells her that she doesn’t need to and he will do it for her.

9. Err, not knowing basic facts about the universe:

My really quite intelligent daughter once dated a lad who didn’t know the difference between the sun and the moon. Not joking.

Edit.. To clarify slightly. Ages – My daughter was 18 and the lad was 20 He thought the moon glowed because it was the same as the sun, ie a ball of nuclear fire.

Although I imagine he knew it wasn’t as hot. He had no idea at all that the moon was reflecting light.

He came from a family of people who saw very little point in education. His mother had never worked, none of his family worked, he didn’t work.

He was actually a nice lad, but difficult to converse with due to his very low level of education.

8. Being like this:

My sister dated this dickhead that would make her cry about once every 2 months. He posted something to Facebook that had a picture of a notebook and something like “If you come home and expect your husband to work around the house, your going to have a bad marriage.” Inside the book. She broke up with him just a month ago

EDIT: thank you u/skaggldrynk for helping me find the original image the guy reposted.

7. Stealing valor as a lifestyle:

My sister dated a guy who lied about being a Navy Seal. Apparently there is like a whole community of people who do that, just go around unemployed living on ??? telling their SOs when they disappear for weeks at a time that they were “deployed.”

It never made any sense to us, and she broke up with him for other reasons and gets really pissed off if anyone mentions the relationship happened. He was a creepy dude who took advantage of her trusting nature and that she was at a low point in her life, and I regret not doing more to call him out on his obvious bullshit.

He’s still in the area doing god knows what, probably trotting out the same crap to new women. I hope one day he gets his ass beat by a real Navy Seal!

6. Killing their dog:

Not my kid, but my brother. He dated this crazy possessive chick who once buried one of his shirts because another girl complemented him on it in front of her.

She also totaled his car after lying and saying she had gotten her licence back. She gave $400 to a fake iPhone scammer website Western Union because, “they are a legit company, I saw pictures of their warehouse and everything.”

Igoogled warehouse, the picture on their site was the first one that came up. She even paid $100 more to “expedite through customs” when the delivery didn’t arrive when expected.

And the pièce de résistance she killed his dog, she left Excedrin PM on the coffee table and he chewed up the bottle. By some miracle no pills got out and crisis averted, it was explained to her that the pills would be fatal to the dog.

She bought another bottle and left it on the coffee table again this time dog ate half the bottle and his kidneys failed, sucks because he was the sweetest/ smartest dog I’ve ever known.

TLDR: Bro dated a girl that killed his car and dog

5. Or any kind of violence against dogs, really:

Brothers girlfriend hit my English bulldog with a shovel because “he was barking and it scared [her]” as she showed up unexpectedly at my parents house around 1 am.

He is still with her because “shes lonely and has no friends or family”. Maybe because shes a psychotic bitch?!

4. Ruining the lives of everyone around them:

My brother is currently dating and engaged to one of the worst people I’ve ever met. She is manipulative and controlling.

She likes to do shitty, mean things, and when confronted will act completely innocent and play the victim, and she has on several occasions made up stories and lied for the sole purpose of causing chaos.

She almost destroyed my other brother’s marriage (his wife is her best friend) and has all but ruined my brother’s relationship with our mom and other sister.

I really think she is entertained by the misery she causes. The best part of all of it? They are getting married in 11 days.

3. Being a Tim Burton character:

My grandma regularly thanked my wife for not being my ex girlfriend. When people asked why, she referred to this incident in particular.

I invited my girlfriend over for dinner to meet my family. To envision this imagine a tall, deathly pale girl with long, black hair that regularly falls over her face. If you’re imagining the girl from The Ring except older you are exactly right.

My grandma immediately tries to make polite small talk once everyone is seated. “So, (girlfriend at the time), what do you do for fun?”

Girlfriend looks up through her creepy hair curtain. “I like scissors.”

There is an awkward silence.

My grandma doesn’t ask her any more questions.

To be entirely fair to my ex she did collect different varieties of antique scissors but that doesn’t make her sound any less weird when I type it out.

2. Being a lazy person who is into crystals and sells drugs:

My sister is currently dating a dude that’s a huge ‘hippie’, just like her.

Really into the stars, soul mates, drugs…. and other sh*t.

Of all the issues I have with him, he had told us that he was on an acid trip once and that his carpet spoke to him and told him he’s not allowed to hold down a job for more than a week because it unaligns your Chakra points and throws off your energy.

It also feeds your energy into the big ‘alman matter’ aka the government and with every hour worked you’re making them stronger.

To make money he does what you would expect him to do (sells drugs, sells his food stamps, asks my sister for money… Etc).

1. Ok, this one is long…but worth it.

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 BF, 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 drug dealer. He had been in the Army for a few years before getting dishonorably discharged for drug 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 rape (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 PoS” evidence).

My wife immediately called our daughter to tell her this and to try and 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 raped 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 ahold 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.

Edit: thanks for all the kind words of support everyone. My wife is of the same mind as most of you it seems, she avoids any hint of “I told you so” and we ensure she knows she is always welcome back and we’ll cover the trip.