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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.