Parents Explain The Biggest Loser Their Child Has Ever Dated

Parents don’t always like the people their children date. Sometimes, parents are too hard on their kids’ significant others, but there are plenty of times when parents are right about the losers that pass through their kids’ love lives. Then again, I suppose we all have to date some of those losers who won’t get out of the car when they pick us up in order to figure out who the good ones are. When it’s all said and done, parents don’t seem to be shy when it comes to talking about the losers their children have dated, as seen from the horror stories below. A few other family members don’t mind chiming in either.


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My daughter once brought her boyfriend over for dinner. They were both 16, things were going well; he seemed a little nervous, but it’s understandable. My wife served dinner: steak and baked potatoes. This kid grabbed the baked potato in his hand and bit it like an apple. Apparently, this little freak not only never had a baked potato, but had never even heard of potatoes. I promptly kicked him out of my house. I can’t have a boy who doesn’t appreciate steak and potatoes with my daughter.


SF Gate

34. Not The Smartest Or Sanest Girl Around

This was not my kid, but my brother. He dated this crazy possessive woman 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 license back. She gave $400 to a fake iPhone scammer website because “they are a legit company, I saw pictures of their warehouse and everything.” I Googled the word “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 my brother’s dog. She left Excedrin PM on the coffee table and he chewed up the bottle. By some miracle, no pills got out that time and the crisis was 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.

33. Impersonate To Impress

My sister dated a guy who lied about being a Navy Seal. Apparently, there is a whole community of people who do that: just go around unemployed; disappearing for weeks at a time and telling their significant others that they were “deployed”. It never made any sense to us. She broke up with him for other reasons and gets really pissed off if anyone mentions the relationship even happened.

He was a creepy guy who took advantage of her trusting nature. I regret not doing more to call him out on his obvious nonsense. He’s still in the area doing who knows what, probably trotting out the same lies to new women. I hope one day he gets beat by a real Navy Seal!



32. 14-Year-Old Meets A Guy On Internet And You’ll Never Guess What Happens Next

When my niece was 14, she met a guy on the internet who was 22 and from across the country. We were not happy. He came to visit and he was the weirdest guy I ever met. I was only 4 years older and tried to have conversations with him but he was just monosyllabic. Exactly the kind of guy who you would expect to hit on 14-year-olds in anime forums on the internet. Of course, we watched them like a hawk and they were never left alone together.

I still admire my sister. She firmly put down the rules (no being alone together, no sleeping in the same room etc.) but never said anything against the “relationship”. The whole thing ended pretty much right after his visit. If my sister had forbidden it, I am sure it would have gone on much longer.



31. Dads Will Not Have Any Of That

This little twerp who my daughter had a crush on couldn’t be bothered to come to the door when he tried to pick her up for a date. Her dad marched out to the street and told him to get his butt inside for a few minutes or he could just move on. Weirdly, they didn’t last as a couple.

30. Loser Turned Millionaire…Oops

Our daughter dated the same guy all through high school. He was a nice guy, but unmotivated. He ate most dinners with us and bummed off her all the time. She broke up with him when she went away to college. I was kind of relieved. He did nothing the year after high school and then finally got a flunky delivery job at a dental lab. After a year or so, he started helping make dentures. It seems as though he had a natural talent. By the time our daughter graduated, he had purchased the lab from the owner who retired. By the second year as owner, he had made his first million. Our daughter sells t-shirts. Guess he wasn’t the loser, more like the one that got away.



29. Controlling Is An Understatement

My son was dating a girl who kept needing a place to stay, wouldn’t help out around the house, made sure she had his social media passwords, and threatened to cut up all his clothes because he took a shower without her. My other kids overheard her screaming at him. Of course, nothing I said could make him leave her, but after a year of this nonsense, he’s finally moved on.


Psychology Today

28. No One Needs College

My daughter dated a horrible guy in high school. You know the type: wispy facial hair, jeans so skinny I’m not sure his man-parts would fit inside, wool hat in the middle of summer. He tried to convince her not to go to college because it was “ridiculous” and “no one needs college”. We had a discussion where I tossed him off the front porch like Uncle Phil. He could run really fast for a guy wearing his little sister’s jeans. I never saw him again. She went to college, graduated, and got a great job.



27. Surprise, Surprise

So I was a drug counselor at a high school and worked with a kid named Bobby. He was pretty sweet, but he was also a terrible drug addict and dumb as a doornail. He transferred and I stopped hearing from him.

I go to pick up my daughter from school one day, roll down the window and hear “Hey Moz!” (which was the nickname my students gave me at my work). There was Bobby, with his arm around my daughter.

A few weeks later, he was arrested for robbing a pizza guy with a flare gun. That was a pizza guy who he called to his own house. Needless to say, he was out of our lives after that.


Carolina Parent

26. Not Your Average Crazy Ex

I was probably around six at the time. My brother had a girlfriend who went psycho after their breakup, and she tried running over me whenever my brother and I were outside playing football.



25. Tantrums Aren’t Just For Toddlers

My cousin dated a woman who came to our Thanksgiving. She was probably in her early 30s. She spilled some red wine on the carpet, sat there while I cleaned it up, then threw a temper tantrum and cried to my cousin because she wanted to leave. She ended up sitting in the car— without heat in 35° weather — through the rest of dinner and dessert.

24. Age Ain’t Nothin’ But A Number

Our daughter, as a teen, dated a guy who seemed ok. He was a few years older than her, but I didn’t like guys my age either. Meeting his parents made me uneasy because the dad was overbearing.

The guy would say, “If you don’t do a certain chore, I’ll break up with you.” Our daughter figured out it was an empty threat. At the same time, he wanted a puppy who turned out to be destructive and had to be crated while they worked. This guy threatened to break up with my daughter. Again.

This time, she said if he continued to treat her in that way, SHE would break up with HIM. He, of course, thought she wouldn’t follow through. But she did. She broke his heart.

She felt bad for him, but was mature enough to understand it wasn’t her fault. In short, she outgrew a man several years older than she was.



23. The Boy That Broke Their Family

Our daughter was 14 when she met him in 9th grade. He came from a good family, but had a bad reputation and had been expelled from school for drugs. She quit all sports, and became completely nasty and defiant. There was a lot of drama that lasted a year. She was never the same and will not ever talk about that time in her life, even now. She is in her 20s and is still in some ways is stuck in that nasty place. Permanent damage through drugs, mental abuse. She got into a really tough crowd for the rest of high school, then moved far away. We’re estranged, and I’ll never know why. It has broken our family.


Ask About Alcohol

22. “But I’m Her Cousin!”

My cousin dated a guy who tried to pick a fight with me because he didn’t want other guys talking to her. I gave him a piece of my mind since I’m her cousin and we’ve been thick as thieves since childhood.


Bloody Elbow

21. Gaslighting And Abuse Go Hand-In-Hand

My daughter dated a guy who was a lying, lazy, abusive, gaslighting type. Besides that, he dropped out of high school at 14, never attempted to get a GED/diploma equivalency, and had more than one conviction for public intoxication/underage drinking/drunk driving. This left him “unable” to get a job for approximately 18 months of the about 2 years they were together. He got fired from Walmart for missing work after only working two weeks working there. He claimed it was because his kid was a victim of an abduction attempt (turns out the kid made it up). He smoked marijuana in my daughter’s apartment bathroom, knowing that if she failed a drug screen her career would be ruined.

He had his two kids every other weekend but spent the entire time with headphones on, gaming, meaning my daughter had to watch his kids or they’d destroy her apartment. He would only eat corn or potatoes, hamburgers or chicken fingers, or pizza, but fast food was A-ok. He never picked up after himself, so every horizontal surface was covered in half-drunk pop cans, fast food wrappers, cups and bags, dirty plates, and moldy food He punched a hole in my daughter’s apartment wall, held a gun to his own head, and then laughed at her for taking him seriously. He constantly accused her of cheating, so she had to unfriend all males on her Facebook, including her father. He threatened to leave when her anxiety and depression had her sleeping anytime she wasn’t at work; and when she finally took him up on his bluff, it was during a terrifying food-throwing, soda-hurling, furniture-smashing temper tantrum that had her grab her cats from under the bed and come to my house 50 miles away.

I could go on, but remembering all that is turning my stomach. In cleaning her apartment afterward, we had to wash the walls from where he had done a Hollywood-style sweep of the coffee table top, spraying Dr. Pepper all over the carpet, TV and stand, wall, canvas art, and the ceiling. Then, for good measure, he smashed the coffee table.

With the help of a therapist, she is finally getting back to the funny, intelligent, confident girl she was before he messed her head up.

20. A Literal Clown

My daughter dated a person who had a job as a clown, and took advantage of her to get fame. I am a very known guy in my profession, and he thought that if he dated my daughter he would get special treatment or something.


Mental Floss

19. Dating A Felon

Daughter dated (almost married) a guy who had outstanding felony warrants (lots of failures to appear, some driving while suspended, some theft/check fraud) in three counties. He told her that he was going to take care of those, and they were nothing to worry about. We ended up calling in a tip to the sheriff’s office, and he was arrested before they could get married.

In the aftermath, we found out that he’d talked her into buying a new truck and trailer and convinced her to lease a skid-steer loader for him. (He couldn’t buy the truck himself, because he had a lifetime suspension.) He had her include his income (which was largely imaginary) on the loan applications. She was actually grateful to us when she found out how much legal trouble he was actually in, and that he’d talked her into committing fraud to buy the truck and trailer.

18. Where Does She Find These Guys?

There was a kid who tried to explain to me how he was going to have sex my daughter and there was nothing I could do about it. That one kinda ties with the one that was a legit drug dealer who sold drugs to my daughter’s friends and tried to get her to drive him to Nevada to go pick up more. The first one I threw over a fence. The second one broke both his ankles while leaping off a parking structure trying to escape the cops. My daughter was angry about the first, but totally okay with ditching the second.


So He Did

17. If Only He Hadn’t Been So Homophobic

One guy drew a bikini onto his tattoo of a naked girl riding a torpedo before coming to dinner in a sleeveless shirt and a tie.

Honestly, I didn’t hate his style. He just was a super homophobic cold-brew of toxic masculinity.



16. Enough About The Strippers

I took them both out to dinner and her boyfriend starts going on and on about some reality show he saw where they had a stripper pole. He kept going on and on about how cool it was. On. And. On. He was 14, but still.



15. She Was Hiding Him For A Reason

My daughter, during her senior year of high school, started dating a new guy she met through a “friend,” but was REALLY sketchy about us meeting him. She had her own car and would always drive, so he didn’t have to come by the house.

Finally sorted out that he was like 25, missing teeth, tattooed up, and generally looked like a druggie. He apparently worked part-time painting and otherwise just slacked around. To this day, I have zero ideas what she saw in him.

Anyhow, she almost blew off college to stay with him but ended up going. Even though the school was 4 hours away, she’d try to come home every weekend to see him.

Shortly after, he apparently relapsed into drug use and OD’d. She’s since turned her life mostly around and is making smarter choices.


Love Bondings

14. Far From The Ideal Baby Daddy

My mom would say the worst guy I dated was one that refused to meet her while wearing clothing. He thought it was ridiculous that she wouldn’t meet him naked because she wanted him to “conform”.

This winner also lived with his ex-girlfriend’s mom.

I don’t think there is even a word to describe this kind of person.

13. A Son Gone Estranged

My son is dating (or could be married to by now) a woman who is bipolar, depressed, and suffers from multiple personality disorder. We asked to speak to him without her, and then they both cut off all communication with our entire family: siblings, aunts, uncles, cousins, grandparents, everyone. He deleted Facebook access and recently changed his number. That was 16 months ago. I think they’ve since had a baby.

12. Not The Smartest Cookie Around

My sister dated a guy who got her a “Christmas card,” and by Christmas card, I mean a card he received from his boss at work and he crossed the name out and wrote “love ex”. She doesn’t like to admit she dated him for 2 years.



11. Just A Little Racist

When I met him the first time, he told me and my wife about a fight he got into. He apparently beat up a Native American kid and screamed “White Power!” over him.

He then told me he wasn’t a racist.



10. The Story Of The Two Pet Ducks

My sister dated a guy who proudly introduced us to his two pet ducks. One was named Chuck. The other was named the N word.



9. Bad Boys Tell Lies

Thankfully only one of my kids is old enough to date, and she’s only had one boyfriend. He still qualifies as a huge loser. He skipped lots of school days, smoked pot (not legal here), and regularly drank until she told him to stop. They’re both sixteen. He eventually made up a beaten-and-murdered brother to excuse a drinking binge. There was lots more lying. There was probably more pressure to get her to have sex than she’s willing to tell me. To make things worse, they’re both in JROTC and the first sergeants were encouraging her to whip him into shape like that is somehow what girls are for.

She finally dumped him after a few months, but she’s now insecure about her ability to judge someone’s character.


Pic Jumbo

8. A Fake Pregnancy, Need I Say More?

My cousin’s ex faked a pregnancy (even got fat) so she could have a baby shower and get all sorts of gifts and attention.

When the time came for the baby to come, she went to the hospital and said she had a miscarriage. The lie got revealed when my very religious family wanted to see the baby / have a funeral for them, but there was no body. I can’t remember what excuses she tried to make (cremation, maybe?) but eventually she had to admit it was all a lie.



Elite Daily

7. Deadbeat Rich Boy

My daughter dated the son of an NFL coach. This guy (the son) was a complete loser. He didn’t work, stayed home all day playing video games, lived his life stoned, never helped out, and relied on my daughter to support him. He did this despite the fact his family is quite wealthy.

Then he started stealing money from me. Not from my daughter, but from me personally. He somehow linked a Foursquare account to my credit card and began making purchases. By the time I caught him, I’d lost $4,000.

I think my daughter knew about it but didn’t know the extent of it. I say this because after they broke up, I overheard her screaming at this guy on the phone about how his theft ruined her relationship with me. He didn’t ruin it. I was mad of course, but we eventually got past it.

My first instinct was to go after this guy, but the Foursquare account belonged to my daughter and I was afraid she’d get caught up in the criminal investigation, so I just let it go.


Instinct Magazine

6. Lazy Bum Indeed

My daughter dated the laziest human being I could ever imagine for two years in high school. She insisted that he keep a part-time job and get decent grades in school. He said he wanted to be a bum when he grew up and we used to laugh, but he was serious. He dumped her (by text, of course) right before graduation over a year ago, and never did another thing. I’ve heard he’s on heroin and desperately trying to convince the Social Security Administration that he has an untreatable mental illness so he can get disability payments. One of his complaints about her is that she made him graduate high school and he didn’t want to. What a loser.


Today I Found Out

5. First Impressions Can’t Always Be Trusted

My daughter dated a guy who started out very nice.

Then we learned he was a white supremacist with mommy issues and a severely creepy foot fetish. Creepy because he insisted she wear the exact same color nail polish on her feet as his mom… whom they lived with when he convinced her to move to his home state with him. She lasted about three weeks before she came home.


Business Insider

4. The Apple Doesn’t Fall Far From The Mother

Unfortunately, my middle son married the biggest loser he ever dated. Our oldest son was 17 when he dated a girl whose mom was an alcoholic and would call my house all hours of the night threatening my son and myself. He figured out within a couple months that the apple does not fall far from the tree.



3. Dodged That Bullet

Her junior year of high school, my daughter dated this guy. The summer after their junior year, he came back from church camp and broke up with her because his youth leader said she would lead him away from God, since she is atheist.

He tried to get together with her again a year later but she declined. They have remained friends.

On August 10th of this year, he was arrested for 1st-degree sexual assault and child porn.

We both thank a god we don’t believe in for that youth leader.


Sweety High

2. The Precise Reason For Parental Controls

Our 13-year-old tried to date a 17-year-old. When we found out, we made it end. He sent her pictures of handguns threatening to kill her. We sent her to stay with relatives in our home country because she kept trying to sneak around with him. He was trying to get her to run away and live in the desert with him. One year later and he’s in jail for the vehicular manslaughter of 2 people.

1. Laziness Is Not A Virtue

The worst one was a chronically homeless guy in his early 20’s who went from one housing assistance program to another, staying until he aged out or wore out his welcome. He received lots of counseling and job training, but never actually applied for jobs. He just hung out wherever he could, playing computer games and going on Facebook. He was the poster boy for anti-welfare campaigns, blamed the world for his problems, and really didn’t want to improve himself.