Dating is awkward enough by itself, but it gets so much worse when parents get involved! Think about it. What could possibly go wrong when a protective mother or father tries to interact with someone hoping to have a good time with their offspring? Turns out the answer is everything! From horrible first impressions to incredibly embarrassing behavior, there is no shortage of ways that potential mates can go wrong with their partner’s parents. Here are 50 stories to illustrate that point.
1. Breakfast Is The Most Important Meal Of The Day
I’m the awful boyfriend in this case. When I first met my girlfriend's mom for breakfast, I ate the whole family's sausage and bacon thinking it was the plate they had left out for me since I showed up late. They were too nice to say anything about it, though, and it took me a while to realize what I had done wrong. If I had been the parent, I probably would not have been too pleased!
2. A Striking Resemblance
I never in my life thought that I would ever strike a teenager until I saw a boy smack my daughter's rear end right in front of me with impunity. I know I’m supposed to be the adult in this situation, but I’ve never felt more rage or wanted to beat someone up more than I did in that moment. I still hate that little brat to this day…
3. In My Room
Not a parent, but when I brought my first girlfriend home I was too embarrassed to say anything to my parents, so we went directly up to my room and started fooling around. Here's what transpired. My mom opened the door to my bedroom and stopped in the middle of her sentence. "Hey, I was thinking we could have turkey for..."
I slowly and awkwardly removed my hand from the front of my girlfriend’s unbuttoned jeans. She said, "Oh uhm, sorry I didn't realize you had company!" I replied, "Yeah, this is Caitlin." Mom: "Hi, Caitlin. Did you want to join us for supper?" Caitlin: "Suuuuuuuuuurrree." Then we all had a super awkward dinner together. Fun times!
4. Just Let This One Go...
My son's girlfriend just will not stop singing “Let it Go” from the movie Frozen and it is really starting to wear on my son’s patience. And mine. I mean how many times can you hear the same children’s song without going at least a little crazy? Oh, by the way, I should probably mention that they are both only five years old!
5. Well This One Is Different...
I met my current best friend by dating his daughter. His daughter and I didn't last two years, but somehow he and I have been friends for over 35 years. Apparently, all her previous boyfriends had been pieces of trash. One of them was so bad that her dad actually body-slammed him into his car hood over something he said. As much as I love the guy, I know now that I dodged a bullet with his daughter.
Nice enough person, but we would have ended up divorced in less than five years.
6. A Familiar Face
When I was sixteen years old, I met this girl who went to high school across town through a buddy of mine who was dating her friend. Our parents were pretty liberal and we spent most of our weekends partying and having fun in the pool house, then swimming when we wanted to cool off. Needless to say, it only took about three days before I slept with this girl, and it was the awesomest.
Here's the thing. When you're sixteen years old and you find a girl who is down to sleep with you, you never want to let that go. I immediately became her boyfriend. Despite the fact that I didn't know that much about her, I knew everything that I needed to know: Specifically, that she had a lady part and that she let me sleep with her whenever I wanted to. It was a recipe for disaster—and that's just what I got.
During week two of this torrid romance, I started to sense that something wasn't quite right in the land down under. It was really burning when I peed. Like every single time. I went to Catholic school, so I knew all about how Satan invades extra-marital relationships and fills your body parts with diseases. I knew I probably had one, and the only question became which one.
A lot of people would ask me: "This chick just gave you a disease, you dumped her right?" Let me just refer you to the previous statement: I was sixteen and she was letting me sleep with her. We only got more serious from that point on. Like getting close to meeting each other’s parents level serious. Don’t you miss the simplicity of being a teenager?
Unfortunately, love didn't cure whatever evil was festering in my body, and so I had to schedule a doctor's appointment. In the exam room, I had to fess up my suspicions to my doctor. I had to pee in a cup, and he manually examined my private area. He then asked me why I suspected I had caught something, and, in the spirit of doctor-patient confidentiality, I told him everything.
Which came out as "I met a random girl from across town and I've been sleeping with her everywhere: pools, bushes, Suburbans, rugs, carpets, dirt piles. I don't know that much about her, but if she's willing to sleep with me, then she probably gets around a lot." It took a week, but the results finally came back negative. I just had a benign infection, most likely from rolling around with her in piles of dirt.
His advice was to clean up my behavior and not get myself dirty. That was a giant relief, and a huge middle finger to Sister Helen who had convinced me that God punishes all fornicators with a life-long curse of pee fire. Everything seemed to be great. The pee problem cleared up and this girl and I kept seeing each other. After a few months, she invited me to her family dinner to meet her parents.
Her mom was nice and very pretty. Then I realized that her dad was my doctor…
7. Should I Come Back At A Better Time?
The first time that my mother ever met my high school girlfriend was when she accidentally walked into my bedroom at a very awkward time. As she walked in, my girlfriend was completely bare on the bed while I was just sitting there fully clothed and on the computer. None of us were exactly sure of how to react in the moment…
8. Popping The Question
The first time I ever met my ex-girlfriend’s mother, she greeted me with, “Did you convince my daughter to go on birth control so you could sleep with her?!?” I was shocked to say the least and had no idea how to respond. We had only been dating for a few weeks and she was still a virgin. I intentionally wasn't pushing the issue or rushing things, because I really liked her.
In my confused state, my then-girlfriend explained to me that she had told her mom that she wanted to sleep with me that night and that she needed birth control. I knew nothing about it. So yea, my first encounter with an ex-girlfriend’s mom went awfully, and I never recovered from it in her eyes. She has always hated me ever since.
9. Parental Instincts
When my mother was 14 years old, she wanted to date this older boy who was seventeen. My grandparents wouldn't let her, because they said they "just didn't trust him." My mom argued again and again with her parents over this matter, but they stood firm on their decision and did not give in. As a result, my mom did not end up dating this boy.
Flash forward to about eight years later, and my mom is happily married. One morning, her parents show her the newspaper. There was an article showing that the boy, who was all grown up by now, made the news. A dangerous substance sale had gone horribly wrong, resulting in an armed robbery and eventually a double homicide and suicide. I’d say my mom dodged quite the headache…
10. The Lunch Special
Ugh, I was the girlfriend in question. I had come over to my long-distance relationship boyfriend's apartment on the way out of town. I had dressed in a plaid skirt, fishnet stockings, combat boots, and a low cut black tank top because I wanted to leave him with a good memory. So, he's got me pinned face-first against the wall with my skirt flipped up and he's going to town on me.
Just then, his dad walks in. Apparently, he had unexpectedly come by early to take his son out to lunch and drop him off at his job. I made quite the first impression on him. He awkwardly invited me to join them for lunch. I was absolutely mortified during the entire lunch with my boyfriend, his dad, and his dad's girlfriend.
11. An Eye For Fashion
One year, I was over at my boyfriend's family's house for Easter where we all got together for an Easter egg hunt, dinner, and party games. My boyfriend's middle sister had recently started seeing a guy she had met on eHarmony, who apparently lived in Toronto. She spent the afternoon telling us all about him. She had plenty of positive things to say about him.
She told us that he owned a delivery business and a flower shop, that he was originally from somewhere in Africa but eventually moved to the United Kingdom and then here, etc. My boyfriend's brother joked that he was probably an illicit substance dealer for his “delivery business,” and we all laughed as she tried to defend him.
Anyway, he finally drives up in a very expensive car, wearing a t-shirt with arrows pointing to the shoulders and the caption "Place legs here" written across the chest. Our jaws all collectively dropped. Everyone started interrogating him, but he was avoidant of everything he was being asked. I worked in a flower shop for seven years, and he couldn't name any flowers.
Granted, his English wasn't perfect and he was a very awkward speaker, but the possibility of him being an illicit substance dealer looked more and more likely as time went on. In the weeks following that dinner, he turned into a full-blown creepy stalker. She broke up with him since he couldn't explain any of his creepy behaviors, and he sent her more than forty text messages trying to get her back.
He wrote and sent her a whole bunch of poems about how much it hurt to miss her. He also said he'd drop by her place of work if she didn’t respond to him. She blocked his number, reported him on eHarmony, and everyone in the family has since sworn a pact to immediately call the authorities if we see him hanging around us anywhere. It was like standing next to a trainwreck as it happened.
12. Baby, You Can Drive My Car
When I was an angsty youth, I used to fool around with my girlfriend in the backseat of her family’s car while her parents sat in the front, driving us around. I used to think I was being discrete and that no one would notice what I was up to, but in hindsight, they definitely knew what was going on. I would beat the heck out of 15-year-old me. I can only imagine what her parents must have thought of me…
13. A Tired Out Story
The first time that I ever met my daughter’s boyfriend, he jokingly recounted the story of when he drove home so intoxicated that he lost a tire hitting something. He then apparently drove on the rim for at least the next four miles down the interstate. Thankfully he's sober now, but is that really something you want to talk about the first time you ever meet me?
14. Pizza Party Gone Wrong
I was working at a pizza place in my teenage years and started talking to this girl who I worked with. She came over to my house one night when my parents were fast asleep. My mother is hard of hearing and my father is a rock when he's asleep. She comes over and we start fooling around. Eventually, we both pass out for the night.
I was thinking that since the next day was a workday, she could leave in the morning after my parents had both left for work. We wake up in the morning and are both naked. So, being 17 and looking at a naked girl, we start to fool around again. When we’re finished, she starts crying and saying it hurts a lot. We leave my room to go to the bathroom so she can wash herself off. We didn't know it yet, but we were making a huge mistake.
Now, you have to pass the computer room to get to the bathroom, and guess who's sitting there. My mom. Apparently, she had taken the day off to pick up my cousin from the airport and was on TMZ.com wasting time. Her reaction was quite priceless and humiliating as she turned to say good morning and saw me and this girl she had never met before, both butt naked.
And that was the last time she came over to my house. Work at the pizza shop was pretty awkward between us from that day on, too…
15. Let’s Never Speak Of This Moment Again...
The first time that my dad ever met one of my girlfriends from college was when he just waltzed into my room unexpectedly and found us in the middle of sleeping together, doggy style, facing the door. Those two seconds of eye contact between us felt like a lifetime. He never mentioned it again though. I like to think he felt an ounce of pride, and he got to see some attractive breasts. You’re welcome, dad!
16. I Know What You Know
Before we started dating each other officially, this girl and I had a kind of friends with benefits thing going on. And this girl has the tendency to tell EVERYTHING to her mom. So, she told her all about how much we slept together, about my recreational substance use, about our drinking till we both passed out, all of that embarrassing type of stuff.
This was all good and well because I never met the mom. But now that we’ve officially become a couple, I frequently have to sit across from her at the dinner table knowing good and well that she knows I got intoxicated, did a bunch of substances, and slept with her daughter in a dingy bar after closing time. Fun times…
17. Call Me Old Fashioned...
As if coming out as gay to my parents wasn't already a shocking bit of news, I think I horrified them permanently when I brought my new boyfriend home a year later only for them to realize that he was around the same age as them. I then had to break the news to them that I'm only interested in men who are far older than my age.
We've been together for almost five years now and finally got married just two months ago! Amazingly, my parents are now very accepting of us both. Strangely, they were more bummed out by the shock of me being gay than they were about the age difference thing. Nevertheless, I cringed pretty hard at that first impression…
18. The Bear Necessities
When I brought my first serious boyfriend home to meet my mom for the first time, he was wearing a Misfits sweatshirt. My mom, bless her heart, completely ignored his dyed mohawk, gaged ears, and pierced nose, and said that she liked his panda sweatshirt. I laughed so hard I literally cried. I’ve got to give him credit though, he stuck around with me for four years.
19. Making an Entrance
When I was in the ninth grade, I went to my girlfriend's house one time while her parents were supposed to be at work. We were just hanging out downstairs when her dad comes bursting through the door totally unexpectedly. I still to this day have no idea how he unlocked the door so darn fast! Let’s just say he was not very happy to see me…
He sat me down and talked to me. He gave me a long lecture on morality and trust before he finally asked me whether I thought coming over to someone’s house while no adults were home was the "right" thing to do. I didn’t know how to react, so I just nervously said, "Yes!" I think that just made him hate me even more than he already did…
20. This One Is Out Of Sight...
My boyfriend in high school was a senior at a different school while I was a sophomore. At their school homecoming game, it was a tradition for all seniors to dress up in camouflage. So my mom first met him when he was dressed from head to toe in black and white camouflage. She also wasn't aware of the tradition. As he was walking towards us, she said, "Oh God, no!"
And she didn't realize I had heard her. To be fair, he did turn out to be pure scum…
21. Say It With Music
The first time that I ever met my daughter’s boyfriend, the handsome little idiot unabashedly sang an explicit song he had written about what screwing my hot daughter was like. Right in front of me. Who does that? Let’s just say it made a terrible first impression on me. I was not impressed, and I still think that this guy is a total idiot to this day.
22. Second Time’s The Charm
I had met my girlfriend’s mom briefly once before, but my most awkward meeting with her happened nine years ago when I was 18 years old. I was sitting on the mom's couch chatting with my girlfriend while we secretly texted each other dirty things. We would pretend to talk about being seniors, looking forward to graduating, etc. But the real conversation was happening on our phones.
We were really discussing the dirty and crazy kind of teenage antics that abstinence-only education warned you about. As we texted more, I started to get a little excited. It was nothing I couldn't control but darn, it felt dangerous and naughty which got the adrenaline flowing. Her mom was right there in the kitchen the entire time cooking up a meal for us while we secretly had our naughty conversation in plain sight.
I then told my girlfriend to put her phone between her legs while it was on vibrate. She did and I started to call her repeatedly. Watching her get excited over this got me even more excited. The blood must flow! There was no fighting it anymore. My private area was getting bigger knowing that she was ready for some prime time fun.
Let's pause for a second and examine this situation. I'm sitting on the couch as excited as one can be, and she's sitting next to me with a phone between her legs while I call it repeatedly. What 18-year-old guy wouldn't be aroused? However, I wasn't prepared for one thing: How quickly her mom could prepare an entire meal. Panic time.
Her mom walked into the living room all of a sudden to tell us that dinner was done, but that it had to cool down a bit before we could go in and eat. She wanted to take this time to get to know me. I had met her once before but only briefly, so all I had said to her was hi up to this point. She made herself comfortable in the room with us and began to try and chat me up.
She was perched on the arm of the love seat which was at a 90-degree angle to the couch we were sitting on. She sat there like a judging vulture disguised as Bettie Homemaker. Her voice and smile were gentle, but her eyes were fiery and alive like she had plucked them from Hannibal Lecter's head. "Are you excited to graduate?" she asked me.
I replied, "Yes ma'am." When I'm nervous, I get really polite. She said: "Are you two hungry? I made enough to feed everyone and still send you home with plenty of leftovers." I replied: "Thank you, ma'am." My you-know-what was about to burst through my pants, and that whole area was starting to hurt from all the trapped blood.
"Call me Kathy, or Mom if you want to." I'd rather not, I thought to myself. In fact, I'd rather be sewing my wild oats in your daughter and praying for crop failure. Nevertheless, I said: "Okay Kathy, I'll remember that." She then said the sentence that irreversibly changed the course of the evening. "Where are my manners? I almost forgot to mention that we hug in this family!"
Oh Lord, no. Please no. Not now, at this exact moment. I haven't had the chance to covertly tuck my private part into the waistband of my jeans! She insisted: "Stand up and give me a hug, mister." No. no, no, no, no, nononono! There was no way I could have escaped this situation without taking the lives of two people and hiding the bodies. I had no choice.
So I did it. I stood up and hugged this woman. As soon as it happened, I could feel my you-know-what pressing into her. She knew. I knew she knew because she immediately backed away from it. As soon as she did that, I had an involuntary twitch for a split second, causing it to again push it back into her thigh. Uh oh.
We parted from our hug, and we both tried to be polite about it. Neither one of us said anything out loud. But the shame had set in. Dinner was extremely awkward. I wolfed down my food without ever making eye contact with Kathy. I made an excuse to leave right after dinner. I then went home, did some relaxing, and wallowed for the rest of the night in my shame and embarrassment.
23. Dinner Is Served...Or Not
I'm not a parent, but an older brother. My sister once brought a boy home who didn't know how to use a knife and fork. He literally sat there at the table and awkwardly looked around, not knowing what to do with the cutlery. It was not exactly a good first impression. What teenager doesn’t know how to use a fork and knife??
24. History Repeats Itself
A family friend of mine once brought home this guy she was dating to meet us all for the first time. The guy proceeded to tell us, in full seriousness, that he had jumped out of a mission plane during WWI and that he also used to star in some hit television show in Canada. The guy was 33 years old in 2012. Need I say more?
25. He’s Entitled To His Opinion
I’m not a parent, but the night my sister's ex-boyfriend met our parents, he made a terrible first impression. He went off on a tangent about how proud he was not to work, and how good it is that the state gives him food stamps and welfare. My dad, who's been a consistently hard worker his entire life, just about blew a fuse that night.
The ex continued his idiocy for some time. But shortly after, he recommended to my sister that they move into a Section 8 government housing complex. That's when she finally had the sense to call it quits with him. Nothing against people on welfare, but this guy’s whole attitude towards life and other people was just utterly horrendous.
26. Space Invaders
My son's girlfriend was having some intimate conversations with my son in the living room, even though I was sitting right there. I coughed, and left to give them some space. I thought that was a reasonable thing to do. But when I came back, I found them sleeping together on the sofa. I had to tell them to stop because my wife was on the way home and she would be very unimpressed.
27. A Weekend They’ll Never Forget
I had never met my boyfriend’s parents before. The first weekend I went to stay with his family, my boyfriend and I played Drinkopoly with some of his friends. Drinkopoly is basically like Monopoly, but you drink instead of using money. All was grand. I went to bed a little earlier than everyone else, and my boyfriend's friends left saying, "She drinks pretty well for a girl!"
He comes up to bed, and I immediately start to feel like something is not quite right. I then proceed to throw up everywhere. On him, on his sheets, on myself. He put me in the shower and I apparently screamed random numbers at him and got angry when he didn't understand what I was trying to say. I’m told that his parents showed up while this was going on.
I probably made a terrible first impression on them. But they were ridiculously cool about the whole thing. The next day, as my boyfriend slept off the trauma, I washed the puke off his sheets and then went with his mum to play with the cats that they were soon to adopt. Oh, and then the next day his younger sister walked in on us sleeping together.
I still don't understand how anyone in his family likes me...
28. The Shoe Must Go On
My father hated one of my old boyfriends because he came to the front door with his shoelaces untied the first time they met each other. He said it made him look lazy and poorly groomed. He never got over that first impression. I guess he was onto something in the end, because I didn’t end up staying with the guy for very long.
29. Time Is On Your Side
This was my daughter’s first and current boyfriend. She's 16 and "in love." I'm trying to be supportive of her, but this boy is a complete idiot. He frequently blows her off to play video games, is never on time when they're supposed to meet up, comes everywhere hours late, and just doesn't seem to at all appreciate her or her time.
I've told her my thoughts on this multiple times, and have subtly suggested maybe they should take "a break." Unfortunately, they're still together for the time being.
30. Yes, We Have No Mangos
One time, I had been saving a mango for days waiting for it to reach that perfect ripeness. I almost ate it early one evening, but decided that one more night would be worth the wait for that perfect taste. The following day, my daughter's jerk of a then-boyfriend decided to eat that perfectly ripe mango before I came home from work.
He never even asked permission. Just helped himself to something in someone else’s house. I never forgave him! Also, he was an entitled jerk in many other ways!
31. A Moment Of Truth
Big sister here. My dad, and the entire rest of our family, absolutely despised my baby sister's boyfriend. He was a condescending jerk that gave her an eating disorder, among many other mental health issues. One morning, she walks into the living room with a black eye. That's when we finally snapped. Every one of us was ready to end that piece of trash’s life.
It turned out that she had just dropped her phone onto her face. But the fact that we all believed he was capable of that really shook her to her core. I had warring feelings when they broke up. I felt bad for her because of how absolutely devastated she was, but I was happier than a pig in poop that the destructive relationship didn't last. I also happened to get dumped the same day, so, joy.
Fast forward a few months and one of her best friends finally works up the courage to ask her out. It only took him four years. It's longer distance because they are in colleges in different states, but she saw the immediate difference when the first weekend he drove out to her dorm because he wanted to see her and spend time with her.
Flash forward another three and a half years to this very day. They are getting married in a few months, and he's already a part of the family as far as we are all concerned.
32. Bottled Up Emotions
My dad really hated my high school boyfriend because the first time they ever met one another, my boyfriend had unsolicitedly given him an entire lecture about how to make substance paraphernalia out of a pomegranate juice bottle. This did not impress my father, and he was never able to see past it for as long as I was with that guy.
33. Taking Measurements
In high school, when I met my girlfriend’s father for the first time, he asked me how long my arms were. I said I didn’t know, and I guessed they were maybe 32 inches or so. His reply was “In that case, I want Amy at least 36 inches away from you at all times.” Yikes. Message received. I don’t know why, but I’m guessing he didn’t like me very much...
34. Nothing But A Little Horseplay
I personally have never hated any of my children's love interests, but I do remember having a girlfriend of my own back in the day who's father hated me so much he thought it'd be funny to put me on a horse that wasn't tame and let me ride it. It was my first time around horses and it almost ended with me being thrown to the ground.
The joke’s on him, though, because I married that girl. We get along now. He's not so bad once you get past the trying to injure me bit.
35. Fancy Meeting You Here
I know a girl who visited a doctor after she did a pregnancy test. She has a boyfriend, but his parents didn't know about her yet. Two days later, the doctor's son brings his girlfriend home for dinner. Yep, you guessed it. It was awkward to say the least. Also not the kind of first impression that would lead to a positive relationship between them…
36. Holding His Tongue
My father HATED my first serious boyfriend, but was almost always warm and welcoming to him. I am now 45 years old, and I asked him recently why he didn’t ban me from seeing him or stop him from staying over. His answer was that if he had done that then I’d have just run off with him and gotten married. He said it would have been a total disaster.
He was absolutely right, and I’m so grateful that he let me work things out for myself. Thankfully, I did ultimately realize that I didn’t want to live with a cheating freak for the rest of my life.
37. Great Expectations
It’s funny because my two daughters thought they had a read on me when it came to liking the people they dated, yet both of them didn’t. They thought I wanted the typical male college graduate type from a prosperous family. I don’t know how they came to that conclusion. As far as I’m concerned, it could not be farther from the truth.
In the end, one of my daughters is gay and the other one has fallen for an army guy. I like both of their choices because they both work hard, respect my daughters, and will stand up even to me to defend them. Not viciously or anything like that. The boyfriend I hated was the one where my daughter was trying to please me.
He had been going to engineering school, came from a prosperous family, had a nice car, and always got good grades. But he was a complete jerk as a person. He would pressure her to do things that got her into trouble. He would also make her think he wanted to marry her in high school if she would wait. He was manipulative and wasn’t respectful of my daughter, me, or my wife.
I’m very glad that he has since moved and is out of the picture. The new guy has nothing but respect and a hard work ethic.
38. That Doggone Jerk!
My stepdad absolutely hated my ex-boyfriend. At the time, I couldn’t understand it and thought he was just being judgemental. But looking back, I can see why he did. The guy would always ask for lifts home if he came around. Didn’t wait for anyone to offer, he’d just straight up ask. He also thought it was okay to smoke out of my house’s window.
I was always trying to impress him by acting as if that was fine. He also repeatedly insisted on bringing his dog over despite the fact that my stepdad was allergic to it. This guy really thought he could get away with manipulating and taking advantage of people because he was charming. I’m so glad that my stepdad saw right through him.
39. Working From Home
Not the dad but the boyfriend here. I went to pick her up one evening and she informed me that if he ever saw me on their property again he'd put a round in me. Turns out I worked for him as a taxi driver, and he did not like me as an employee, so he did not approve of me dating his daughter. The punchline? It's been twenty years now that his baby and I have been married.
40. Like Father Like Son-In-Law?
My best friend was a huge womanizing loser in his twenties. He slept around a ton. He frequently made a habit of using women and taking advantage of them. He was extremely manipulative. Honestly, he was a jerk in general. He's really grown up a lot since then, though. He now has a successful career and has settled down.
He's married now and has a daughter. They're expecting another daughter. I laughed so hard when he found out he was having a girl. He was everything a father would warn their daughters about. I can't wait for the dating time in their life to come around. I already know he will hate any boyfriend who reminds him of himself...
41. The Warning Signs Were There
My least favorite boyfriend of my daughter’s was the one who became her first husband. The reason I didn’t like him was because I knew his parents, and I also knew that spousal abuse is a learned behavior. Unfortunately, my intuition turned out to be correct. Thankfully, though, they are no longer married and she has moved on to better people.
42. I Urge You To Use Better Judgement
My dad absolutely hated the boyfriend who traumatized me, so I guess that’s no surprise. This ex was the worst piece of garbage I have ever been with. He wasn’t only lousy towards me, but towards me but my family too. Especially towards my dad. Then again, this jerk was probably a psychopath. I should have known that something was wrong when he was discharged from army boot camp over “homicidal urges.”
43. He Had An Ace Up His Sleeve
I’ll never forget the day I first met one of my daughter’s boyfriends. The guy comes rolling down the driveway on a ratted out, semi-bobbed Honda motorcycle with no baffles in the exhaust. He stood about 5'7", 120 lbs, wearing a leather vest, no shirt, biker chaps, and zero helmets on the bike. I thought it had to be some kind of practical joke.
He introduced himself to us as "Ace." He told me this from behind aviators that were much too large. He was clearly an arrogant little fellow. He attempts to fist bump me at the door, calls me "dude," and calls my 18-year-old daughter "Sweet Cheeks" when she walks out of the house. Guess who stayed home and watched movies with her daddy that night?
44. Gaming The System
My sister-in-law’s last boyfriend was a pile of trash. It wasn't just my parents who hated him—all of us did. He frequently made inappropriate jokes about their bedroom life in front of the family. Also, he was always talking smack about others behind their back. He literally just played video games all day and relied on her to pay for his food and rent. He did carry me to some Call of Duty: Warzone victories though, so there was at least one positive out of the relationship.
45. Hitting The Jackpot
My parents weren’t keen on my boyfriend because he was the type who could frequently make money appear out of nowhere. They found this suspicious, and they thought of him as being a hustler. Turns out he is just a very good businessman. I ended up marrying him and he is a great father and husband. My parents love him now.
46. Family First
Brother with a sister here. The boyfriend that my family hated the most was the one that came back into her life many years later and talked her into leaving her husband of 25 years and their two kids. I don’t know how or why he decided to do this, but he somehow convinced her to listen and she moved in with him. No one in my family likes him now.
47. Shooting His Shot
I had terrible taste in boyfriends growing up, and my dad hated all of them as a result. So when I brought my now-husband home to meet him for the first time, my dad was literally cleaning his guns in the living room to try and intimidate him. It was quite the first impression, and their relationship was pretty awkward at first. But then my dad was impressed when he recognized the guns and started chatting about them confidently.
48. Could You Give Me A Hand?
When I first met my ex's dad, I thought in my young, naive, 17-year-old brain that it would be a great idea to go in for a big, manly handshake. What I didn’t realize was that the poor guy had just broken his wrist in a cycling accident the week before. It was horrifying. I can still hear the loud crack it made in my nightmares. I also may or may not have let him drive himself to the hospital while I had disappointing teenage relations with his daughter…
49. Handing Him A Solid Defeat
My grandma once told me about a neighboring family that had a "bit of a spat" as she called it, out on their front lawn. The daughter was all in tears and trying to get away from the boyfriend. I guess they were probably in their late teens or early twenties. This was back in the 1950s. Apparently, the girl’s father had come outside to see what all the fuss was about.
The father was known as the meekest, kindest, most mild-mannered guy on the street. Yet when he came out the door, the young man got really mad and said something to the effect of, “This is what you get for dragging your parents into our problem!” He then flat out punched the girl right in front of the dad. Grandma said he hit her really hard.
The dad went absolutely postal when he saw that. He was a veteran, as many men of his age were back then. Grandma said it showed as he unleashed upon the guy. She had never witnessed such savagery in her life. He beat the boyfriend up for fifteen solid minutes. As sirens were heard approaching in the distance, he went inside and reemerged with a large knife.
He proceeded to cut both of the boyfriend’s hands off about mid-way between his wrists and his elbows. He then sat sobbing for an hour on the sidewalk with his daughter, waiting to see what would happen when the authorities heard the story. Grandma said he was never busted and that the boyfriend turned out to be a wanted criminal.
I think it’s safe to say this dad was not very fond of his daughter’s boyfriend…