It's always going to be a little weird when a new step-parent is introduced to the family...but these awkward folks truly took it to the next level.
1. Mom, You’re Embarrassing Me!
My mom came out as a lesbian when she divorced my dad. She dated several different women around her same age, but she's now settled on one that isn't younger than me but definitely would be considered my peer. She is 33, I'm 30, and my mom is 50. It's very awkward around them with the age difference and the public smooches on top of it.
I don’t have any issues with gay people, but here's the thing—when your own mother is making out with someone your age in public, it's really weird. Anyway, I just try not to pay any mind because we love who we love and although I'm not super fond of my mother's partner, I'm glad mom has somebody to lean on because she has severe depression and doesn't live very close to me or my brothers.
2. The Troublemaker
Six months ago, my 71-year-old dad left my mom for another woman. Their age gap is unbelievable—she's 25 years old, whereas I’m 33 and my sister is 28.
She's currently six months pregnant, but they’re not married because my parents’ divorce hasn’t gone through yet. Once that happens, I’ll have a stepmom who is eight years younger than me, plus a newborn half-sister. This will be my dad’s third marriage. The first one ended because he slept with his brother’s wife.
3. Time Heals All
My parents divorced when I was in high school, then my dad got remarried to someone who was a few months younger than me. The worst part? They went through with it during my last year of college. My relationship with my dad is still the same as it always was, and my older sister feels the same, but my mom was livid and bitter for the first two years of his new marriage. She eventually got over it after seeing my sister and me accept our new stepmom.
Sometime later, started dating too, but she and my dad are still on bad terms as most divorced people are. As for our new stepmom, it's weird because she’s basically the same age as us. It took a while to get used to it, but we’re on good terms. The important thing is that we know she takes care of our dad and that she makes him happy.
We refer to her by her first name, and there’s an understanding that she has no authority over us. In that sense, she feels more like a cousin than a parent.
4. Stop It, Sister!
My dad is married to a woman who is 10 years younger than me. She ended up being like the annoying little sister I never had. I stayed with them for a few years while I was trying to go back to school, and she would go through my stuff and take my things without asking. When I saw her wearing my shirt, I asked her about it. Her response made me livid. She said she found it in the laundry room and she simply assumed I didn't want it anymore.
She would also take the things I just bought, simply because she liked them. Oh, and by the way—she doesn't work either!!
5. Two Feels Like Twenty
My parents got divorced when I was nine, and within a couple of years, we all came to terms that it was for the best. When I turned fifteen, my dad remarried a woman who was two years older than my older brother. She already had three kids by the time she met my dad and she had also gone through some serious events in her life, so her life experience was more on par with my dad’s.
But here's the interesting part about all this—by contrast, my older brother was a bit of a screw-up and very immature, so it always felt like there were twenty years between them, instead of two. All in all, she had been a perfect match with my dad, and they are one of the best couples I know. I’m super glad they have each other, and all of their kids have a great relationship too. My mom couldn’t care less. They aren’t in each other’s lives anymore except as an extension of us.
She does her thing; my dad does his. They are just happy in their own lives.
6. A Problematic Father
My parents married young, as was typical in the '60s. A decade into their marriage, he was caught with our babysitter. He eventually left our mom and married her, but that only lasted a few years. My dad then played the knight in shining armor to a succession of young women who were ‘down on their luck.’ It was the same pattern over and over.
They were always about the same age–late teens to early twenties. It didn’t matter how old my dad got, or how much older we, his children, were compared to them. Ultimately, his work took him to the Philippines, and he became involved with a young woman there. He said they were just friends and all of his many trips there were apparently to help her and her family.
We rolled our eyes. Eventually, our dad informed us he married her so she could come to Canada for a better life. We were taken aback when he told us her age—she is about five years younger than the youngest one of us. I don’t have any beef with her. She’s kind, decent, and hardworking, albeit too submissive and deferential to my dad. I’m sure that’s part of what he likes about her.
My problem is really with my dad alone, who has repeatedly proven himself to be a self-centered narcissist fixated on younger women. He congratulates himself for ‘saving’ all these people and helping them out of their miserable lives when he’s never used the time of day for his own kids or grandkids. He’s lied and broken promises his whole life, and for that reason, I have no respect for him.
When I got married, I would not let him walk me down the aisle. I’ve spent years in therapy trying to untangle a lot of issues surrounding my dad. Although my head knows what he is and that I shouldn’t care about him at all, the sad reality is that part of me inexplicably still wants his love and approval. Not only has he messed up our own relationship, but he’s contributed to my own legacy of being unable to commit. Healing is a long process.
7. New Best Friends
My mother's husband is two years younger than my own husband. That says a lot, considering that my husband is seven years older than me. My stepfather isn't exactly younger than me, but it is still a weird dynamic. My mom jokes that I always date older men, and she always dates younger me, so it was "bound to happen" as she likes to put it.
We actually made a pact when I was twenty that I wouldn't date anyone older than her and she promised she wouldn't date anyone younger than me. We both had some close calls but held true to the pact for the most part. There is, however, one rather weird part about all this—our husbands are seriously best friends. Like, they are super close. Whenever there is a family get-together, if we can't find one of them, we look for the other.
There isn't a cookout or birthday party where they don’t decide to give each other piggyback rides or have a cake eating contest or do something silly and fun. My favorite thing is when my husband yells: "You aren't my real dad, you can't tell me what to do!" They are such goofballs!
8. The Worst Wedding
When I was 19, my dad married someone six months younger than me after meeting her in the psych ward of a hospital. At the time, my father was 39, and he was recovering from an addiction. My father has always dated women much younger than himself, but I was conditioned to it. At the very least, he had never dated younger than me.
I tried to give her the benefit of the doubt, but when he brought her to my cousin’s wedding, chaos ensued. No one had met her until that point, and it was just really messy. My dad and I were really close, but I was edging away from him because his addiction was too much for me to handle. When he married this girl while I was on vacation, it just kind of sealed the deal.
We had always talked about me being his "best man" if he ever got married and it just showed me that I would never matter more than his pleasure and his women. They are now separated, but I still don’t talk to my dad.
9. My Megalomanic
My dad loves controlling people. He used to always go on about wanting an Asian wife because he thought she’d be really grateful and meek towards him. He fancied the idea of not getting into any arguments. Not long after admitting those desires to me, he—in his 50s—met and married a 21-year-old Chinese woman.
I was 23 at the time. The age difference doesn't bother me—however, what is disturbing is my dad's behavior. The way he treats her in public is revolting. He is so condescending and talks really slow like someone would to a toddler. He tells her off and calls her names. It was so sad to see. I don't know for sure, but she may have left him because when I was last in contact with him, he never brought her with him or spoke about her.
10. A Familiar Face…
I don’t have contact often with my biological father, but I knew he’d remarried again. Somebody on my biological father’s side of the family found out about my baby sister’s wedding and they all crashed it. During the reception, a woman I thought looked familiar walked over to me and asked if I was who she thought I was.
I confirmed my identity to her and explained that she looked familiar to me as well, but that I didn’t remember her name. She told me her name and reminded me of a shocking fact— I used to babysit her when I was in high school and she was in middle school. I asked her how she’d been and whose guest she was at the wedding. To my shock, she informed me that she was my biological father’s wife and she wanted to let me know he was hers now.
I was so stunned and not willing to cause a scene I excused myself and left her standing there.
11. So Many Children!
My brother-in-law is 30, and his wife is 55. She has seven children from four previous marriages and relationships. That's bad enough, but it gets worse—three of her seven are over 30 years old. Her youngest is 10 and lives with his father, but the other six are older than 18 and live on their own. At least two are also married. The look on their faces when they came and saw my brother-in-law at the wedding was definitely something to behold!
12. The American Dream
I'm 23 and my dad is 64. Last year, he married a woman who was 22. My parents weren't really together—they never got married, and they split soon after I was born. My mom's black and my dad's an Iranian immigrant who came to the U.S. in the '70s as a student and never left. My dad was pretty transient; he moved up and down the East coast and eventually settled in New Jersey.
I didn't keep much contact with my dad, but I started talking to him again a few years ago. He didn't have much companionship, so eventually he went back to Iran and met a woman who already had a kid and was divorced, looking to make a better life for herself. So, my dad married her, and she and her son came over just before the Trump ban.
My dad talks pretty freely about his relationship with his wife. When he revealed his true feelings, I was caught off-guard. He said things like, "Obviously she doesn't love me. She just used me to come to the U.S." Both my dad's wife and her son have had a hard time learning English. The wife had a mental breakdown last year and checked herself into a psych ward.
My dad's pretty poor and lives in a not-so-good neighborhood with not much to do. It sure seems like my stepmother is isolated, and until she gets used to everything, she's pretty much at my dad's house all day long.
13. The Talk Of The Town
After my mom and her sisters had graduated from high school, my grandparents got divorced. A few years later, my grandpa married one of my aunt’s friends from high school. According to my mom, it was a real big deal that had a lot of people talking. My aunts all hated her instantly, and one of them even did the old “put sugar in the gas tank” thing. But they shouldn't have judged a book by its cover.
Because, oddly enough as it may seem, My grandpa is still married to her, and my step-grandma is a pretty cool person. Everyone seems to get along now. Unfortunately, my grandpa has dementia pretty bad now, and my step-grandma is pretty diligent about caring for him, so I have a lot of respect for her. Tragically, my grandpa doesn’t even know who she is anymore.
14. A Transactional Relationship
My step-grandmother is a fifty-year-old biker chick, covered in tattoos, and she is seven years younger than my mother. My grandmother passed in 2009, leaving my socially inept and cantankerous grandfather behind. He moved to a retirement community, where he’s gotten in some trouble for causing disturbances and being abrasive while on his front porch.
A few years after my grandmother’s death, he started proposing marriage to his housekeeper. He didn’t want her to live with him—he had a very different motive. He just wanted to pass on his pension from work. Only a spouse could inherit it, not children. It took her many years, but eventually, she accepted. No wedding. They’re not really “together.” But now my step-grandmother is younger than my mother.
15. A Partner From "Paradise"
I’m 27 and my stepmom is 26. My dad brought her over from the Philippines and they’ve been married for almost two years now. It was definitely different at first, though I didn’t have much room to talk considering I’ve known a couple of older gentlemen in a very biblical sense. I was most worried about my dad getting hurt or taken advantage of.
They just didn’t seem to have much in common at first other than the fact that they both like to watch 90-Day Fiancé. Once the newness wore off, I saw a startling change in my dad—he was very lonely and needed companionship. My auntie-mama is a lovely young woman who grew up on a poor island with about 15 families on it. She laughs when people call it paradise because she says it’s very hot and there is nothing to do.
I see their marriage as more of an arrangement to better both their situations. They may not be madly in love, but I can tell they care for each other. Now that it’s been about two years, I can say with confidence I get along better with her than with my old man.
16. The Same Sense Of Humor
My dad is married to a 25-year-old waitress. I am 26. When I was 18 or 19, my family used to go to the place she waited at and every time, I would silently pray we were going to be seated in her section because I had a huge crush. My dad would always be a dad and drop some dad jokes, and I always thought she was laughing at those jokes to be polite...but it turns out she thought they were genuinely funny.
Then, my whole world turned upside-down—they got together five years ago, and my crush was quite literally crushed. He still goes to the same place to eat, and she’s still his waitress...but the jokes are worse now.
17. Turning Over Life
I have a friend who is barely 20, yet she is dating a 46-year-old man. He has two sons, aged 20 and 23. They didn’t take the news of him dating a girl younger than them well. How they reacted to it was rather extreme—apparently, they cut off complete contact with him now that things have gotten serious. His ex-wife thinks it’s hilarious, they all think he’s having a midlife crisis, and think my friend is a gold digger. I kind of have to agree with them!
18. The Littlest Sibling
I’m 35 and my dad’s wife is 25. I now have a little sister that is six years younger than my son, who is 10. I always considered my dad an “old” dad when I was younger; much older than my peers’ fathers, anyway, Now he is in his 70s and he's constantly tired of toddler antics. But here's the thing—in all honesty, I love his new wife.
She was not the one who broke up my parents’ marriage and she is the sweetest person ever. She actively plays and interacts with my son and helps with anything I ask. She is genuine and kind. My mom feels the same way and often has both my father and his wife join us for the holidays. My mom has never begrudged my father’s current wife, but it probably took years for her to have an amicable relationship with my dad.
Honestly, I think she feels sorry for his current wife. My mom wants us to have a relationship with our new sister and she does everything she can to foster that.
19. But He’s My Friend!
I'm 34 and my 53-year-old mom married a guy she met in my younger sister's friend group who is around four years younger than me. The age gap between them is staggering—almost 20 whole years. My sister was really mad about it for a while, but I never really cared. It's my mom's fourth marriage, and she has had a very long struggle with mental health issues. I just want her to be happy.
The guy is really nerdy and they had a video game-themed wedding at the local Elks' Lodge. Now they live in an RV with two cats on just his income, because she has been unable to get a job since 2009. I worry about my mom a lot, but for now, it seems to be working okay.
20. A Little More Than Friends
I used to work with a guy named Chris whose best friend David was also his stepdad. Basically, when they were in school, David used to go to Chris' house a lot, and somewhere along the line, David started going over just to see Chris' mom. They started actually seeing each other at some point and eventually got married.
I think David is a year or two younger than Chris. That may seem crazy enough, but it gets even crazier—Chris never moved out, so he's just living there with his mom and his best friend. I never noticed any signs that they found it weird at all, they still came to work together and hung out like friends. It was a weird setup.
21. The Surprise Brother
First of all, my father is no saint. He has cheated on his current wife many times. The step-mom in this story–we’ll call her Linda–was actually his latest mistress. Linda is older than me by two years and younger than my older brother by one year. We first met her on one of our a few weekends away with my dad. The only reason she was there was that my dad knocked her up and she had just given birth to my baby brother.
Because my dad wanted us to have a relationship with him, we got to spend one weekend a month with them at his vacation house. This was a lot of time spent with my dad compared to the last 20 years of my life, so I went along with it despite the whole cheating element. But then the drinking started, and things just really hit the fan.
When they drink, Linda turns into a raging, jealous, paranoid banshee and my dad loses his temper really easily. During one of their many fights, she accused my dad of cheating on her. In a fit of rage, he charged at her, and she reacted in the most shocking way—she actually used my baby brother as a shield. We had to pry my baby brother from her because they were both hurling stuff at each other.
My dad decided to stop drinking but she didn't, despite having a health condition that gets worse when she drinks. Eventually, my dad and Linda broke up (not on good terms), but my dad kept up support for my new brother. When my brother was three or four, Linda took him away and told my dad he couldn't see him anymore. My dad stayed in contact with Linda's mom to get updates about my brother, but he didn’t know where he was.
He sent child support to Linda's mom every month. Linda's mom eventually told my dad the cold, dark truth—the kid wasn't actually his son. Linda had cheated on my dad with her ex-boyfriend and pretended it was my dad's because my dad had more money. As far as I know, my dad has stopped child support, but he checks on him from time to time. The good news is...my dad has sworn off mistresses to live a quieter life.
I mostly feel bad for my non-baby-brother because he's caught up in the middle of this.
22. Wicked Stepmother
My parents were married for 25 years before they divorced. A visiting nanny took great interest in my dad as he was a seemingly easy shortcut to citizenship and comfortable life. She actively pursued my dad, who obviously failed to put up much resistance. My mom found evidence of money transfers and love letters, and that was that. She filed for divorce.
The nanny eventually married my dad, and my sister and I got a stepmom who was younger than us. This woman was a monster. She would monitor all phone calls between my dad and me. She banned him from visiting us at Christmas or during the holidays, and she bought my sister and me a pair of socks each for gifts. In comparison, she treated herself to overseas vacations and ridiculous amounts of plastic surgery.
It wasn’t the gift itself that was the problem, it was the sneer on her face while she handed them to us. Eventually, we just stopped talking to my dad. During this time, mom would receive harassing phone calls that she should give up her house, and in exchange, the nanny would care for my sister and me. We were still in school, and my dad agreed to support us until we finished our post-secondary education.
I believe the demands had to do with both being upset she hadn’t taken our family home as she fantasized she would, and the fact that she thought supporting us directly would cut down their costs significantly. My mom just laughed at the audacity of her calls–they were completely ludicrous. But it gets worse—we later found out that she committed a shocking offense—she had hurt him not once, but twice, after losing her temper.
He had to visit the ER and claimed it was an accident each time. They also managed to have officers ask that they stay out of an entire city after a very public fight at a restaurant. She had also broken countless items around their home while they argued, and basically was totally crazy. The day her citizenship papers arrived, she told my dad she was filing for divorce.
I try not to keep tabs on her but I have recently heard that she married an even older gentleman in his late 80s who is quite wealthy and she is just waiting to collect her inheritance.
23. Solid Parenting
When I was 22, I moved in with my first husband and his three sons from his first marriage. I am four, six, and eight years older than his sons. I threw them their graduation parties, gave them lunch money, busted them when they tried to get away with things, helped them with girl problems and homework, taught them how to drive.. all kinds of normal parental stuff.
I even saw one graduate from boot camp and do two tours overseas. We made some great memories and started new traditions together. I am not just their “Once upon a time” step-mom, but also the mother of their little sister. Unfortunately, like all good things, it came to an end—my ex-husband and I couldn't make our marriage work but we're still pretty decent at co-parenting together.
We talk not just about our daughter, but we also work together and talk frequently about my stepsons. Mostly the youngest, as he still needs the most guidance even though he's 28 now and has little girls of his own. All of us–myself, my ex-husband, our daughter, his long-term girlfriend, his mom, his sister, and the boys all attended my middle son's wedding this past spring, and we sat at the same dinner table together.
24. My Father’s Girlfriend
My father and his girlfriend are only 10 years apart, and she is still older than me, but she is still way younger than most parents of teens around me. My mom is in her early fifties and she thinks it’s weird my dad went from being with someone quite a bit older to someone quite a bit younger. There are also unproven conspiracies about my father cheating on my mom, so neither of them is okay with the other.
I really like having someone younger around, as she is more interested in my music and clothes and classes than my mom, who is basically the opposite of me. She is also more with the times and open-minded to other people’s opinions, which contrasts with both my stubborn parents' thinking. There is one annoying issue, though—since she has been with my dad for 10 years now, she feels like she has the right to parent us, and she sometimes takes it too far.
She and my dad are also disagreeing a lot lately. They argue almost every day and I’ve even seen them go at it multiple times. When I still stayed over with them more often, I could hear up to fifteen fights a day. Regardless, they will be spending two weeks in Europe together soon...Hopefully, that heals them a bit.
25. Building Bridges
I am exactly that stepmom. My partner's oldest kid is two months older than I am, and I'm a year older than his other kid. They both really didn't seem to care about who their dad was dating. Their focus was on something else entirely—they were more interested in the divorce between their parents. I am trying to build a great relationship with them and even with my boyfriend's granddaughter.
I certainly don't try to act like a parental figure to them and wouldn't ever even want them to call me "mom" or anything like that. It's like just being friends with them, which is certainly healthier than them hating my guts or something.
26. The Better Partner
My partner doesn’t have any children, but he is 20 years older than me, and his sister is ten years older than him. Her two daughters are the same age as me, so I have nieces that are almost exactly my age. It was kind of weird when they found out my age, but now it’s all cool. I have a good relationship with the girls and his family loves me in general.
He had been single for a long time before he met me, and before that, he was an absolute menace—he had a terrible partner who stole a lot of money from him and disrespected his family. So, I think they’re all just really happy for him that he has found love with a nice kind person who treats him as he deserves and makes him happy. They’re a great bunch of people and I’m proud to be a part of their family.
27. True Love!
I am 21 and my husband will be 52 this year. He has nine children ranging in age from 11 to 27, so a few of them are older than me. It was weird at first, but I never tried to “parent” them or boss them around at all. We all get along now, and the two youngest girls are my best friends. I am seen more like friends or cousins than anything.
It’s nice because I don’t feel any extra pressure to get along with them. We are all one big crazy family and we joke that we are the “modern family.” My parents had a really tough time with it at the beginning but now they love our relationship. The biggest challenge, however, is something I initially gave no thought to—it's hard to deal with people looking at us in public and assuming that I’m just the “sugar baby” or something along those lines.
But when it’s true love, who cares what other people think? We are so happy now and that’s all I care about.
28. A-Team Of Parents
My husband now is 22 years older than me. He has four kids that are older than me and four that are younger, but they’re all still pretty close in age. Not all of us are close because of life, and there are reasons that don't have anything to do with me. I am closest to two of his sons that are close to me in age. We're basically raising our kids together.
In fact, my daughter goes to school with some of their kids. We help each other out with watching the kids, picking them up from school, and things like that. Nothing has ever been awkward or weird between any of us. The reason for this is simple—I obviously don't treat them as my kids or stepkids since we're all adults. I do love all of the grandkids like they’re my own, but I am well aware of my role.
I don't think they really care about the age difference between their dad and me or that were close in age. I think they only care about his happiness and that I treat him well.
29. About The Wedding Papers…
My parents divorced when I was an infant. When I was 28, my dad married an 18-year-old girl. He needed two witnesses for the wedding and asked me to come, so I did—but I had a surprise move up my sleeve. I'm gay, and I passively-aggressively brought my girlfriend with me. While my dad was never terrible about it, he did kind of just pretend that it wasn't a fact because it bothered him.
For years, I found amusement in that we were the signatures on his wedding certificate. They ended up together so long that I just ended up feeling happy that he was happy and had someone, but I never did form a relationship with her. My mom also ended up later in life with a boyfriend younger than me, but not by as much as my dad’s wife.
I never really liked him much, but she was happy. When she fell ill, he and I made a kind of peace on her behalf. We still talk every now and then. He's still not my favorite person, but when I saw how much he really did care for her, it made me soften a lot towards him. People ask me a bunch if I will follow in their footsteps. So far, not so much. I will say I have more energy and interest in activities my peers are already slowing down around, so who knows.
30. Definitely Not Taking That!
My parents divorced around their mid-to-late-30s. They had me when they were young. When I was 21, I visited my dad's house for the night and a girl he had been dating was over. So, he walked downstairs and asked me what I was up to. He then said the most horrendous thing he's ever told me: “You know, she's about the same age as you, do you want to get intimate with her a little bit? I'm sure she won't mind.”
I declined, then went straight out the door to stay with friends instead.
31. Happy For You, But…
My dad married someone who is not much older than me but is still younger than my older brother. When they got married, she was 30 and my brother was 32. My parents were married for 30 years, but no one was happier than my brother and I when they got divorced. The thing is, I didn’t care about the age difference because my dad seemed to be happy.
But the problem was her. She’s selfish, demanding, and generally just a whiner. One time, she was visiting my husband, son, and me, and she locked herself in the guest room because she thought I hated her for trying to replace my mom. My mom’s still around, I just don’t like you! I tried harder to be nice to her after that, even if I didn’t want to.
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32. Nagging Questions
I'm 33 and I have three younger brothers. My dad is 61 and he's been seeing a 23-year-old girl for eight or nine months now. She lives with him and everything. We live in a smallish town, with close to 9,000 people. For a while, it was the talk of the town. I hated it. Still do, but it's gotten better. I lost a lot of respect for my dad because of it, and it's messed up our family just because it's so freaking awkward.
That's not even the worst part. My brothers and I catch a lot of flack for it. "Hey, how does it feel having a stepmom younger than you?" Stuff like that. It sucks because I've always liked doing stuff with my dad, like hiking, hunting, and fishing, but now it's so weird to be around them.
33. A Young Widow
My best friend was actually married to a man in his late 40s. She's in her early 30s, and his two sons are also in their early 30s, as he had them pretty young. Her husband was in trouble from a mistake a few years ago, and he ended up being diagnosed with cancer, but the place he was held in was pretty negligent when it came to actually getting him proper treatment.
As a result, the worst-case scenario happened—he ended up passing about two months before he was due to be released, so now my best friend is now a widow at 31. Her stepkids are both locked up as well, and they keep asking her for stuff. I'm trying to get it through to her that she doesn't owe them anything, since they're older than she is and they can deal with their own issues.
34. No Kids! (Mostly)
My husband is 15 years older than me and has had a previous marriage. In that marriage, he adopted the ex-wife's two children who are now adults. One is 23 and the other is 26. I'm 33. I entered this marriage with the condition that I'd be childfree for life, and when I told my husband that, I was scared of his response. Luckily, my hubby is also part of that club and wants no additional children.
My relationship with the stepkids is rooted more in friendship than anything else. They have a wonderful relationship with their dad, but I'm not as close as they are, understandably. However, I think they do come to us for help on various issues and we deal with it like any other parent/child relationship. I am the person you go to when you have financial problems and need food or household stuff like toilet paper.
I have all of that in my stock room. I help whenever they ask. My requirement is to simply ask, and I will help however I can.
35. Polar Opposites
My dad is gay, but he was in the closet for most of his life. My mother divorced him when I was two, so I have no memory of them being together. I figured out his secret in a rather disturbing way—it wasn’t hard since my dad doesn’t know how to clear his search history. I’m gay too, but we went for years without addressing his sexuality.
He finally came out to me when I was in my mid-20s and he told me he was seeing someone. His boyfriend was about five years older than me, and about 20 years younger than my dad. It was really heartbreaking because the guy clearly had issues, but I think my dad felt like he couldn’t do any better. My dad has a very stable life, and this guy was a trainwreck.
When I looked into the guy's history, I was shocked. He'd been arrested for distributing illicit substances. For a long time, I was the only one that knew my dad was gay, let alone that he had a partner. When my father had a heart attack, his partner took it upon himself to call my sister and tell her. My sister got a call like: “Hi, I’m Matt, I’m your dad’s boyfriend. Your dad’s gay, by the way. Oh, and he also had a heart attack.”
They were together for three years until Matt passed. My dad swore Matt was done with substances until he started cleaning out his stuff after. I know this is a terrible thing to say, but I’m glad that he’s dead. I hope that my father can find someone who truly deserves him.
36. At Least You Smell Good?
My dad is dating a girl younger than me. I'm 25, she's 23, and he's 50. I hate the looks of other people, and it makes me uncomfortable to be around them. It's so weird for me to watch him teach her how to do laundry or the dishes. It's like he's raising another child. He gets angry that she doesn't know how to cook or clean, but she seems to be trying her best.
She just left her mom's house and now she's supposed to be responsible for taking care of my dad. They also fight all the time because he has zero respect for her. She usually goes and sulks in the car or in their room. There is absolutely zero communication between them. And the cherry on top? My dad usually buys her something after they argue, so nothing really gets resolved.
She has like every scent from Bath and Body Works because that's where he goes after they argue. He used to buy his ex-wife Clinique after they argued so I guess he's lucky the new one likes stuff that is much cheaper.
37. He’s Not Coming Back
At 49, my dad divorced my mom to marry a 25-year-old woman. He had six kids with my mom. The new wife was two years older than his oldest child and is five years older than me. I tried giving her a chance—until I found out what she made my dad do. She made him reverse his vasectomy and have a child, who is 25 years my junior. He stopped paying for college for former kids and stopped paying alimony to my mom after 10 years.
He moved to Texas with his new wife, then retired and eventually passed. His entire estate went to the new wife and her kid. My mom never recovered. She had never finished college, and because she got married and quickly had kids in her early 20s, she had no real means of support. She was always the dominant one in the relationship and she was hurt quite badly by the affair and subsequent divorce.
She always assumed he would come to his senses and come back to her, right up until she got the divorce papers. That knocked her over. Dad then took her youngest kid to live with him, basically saying, "You aren't doing a good job raising him," which messed her up again. No inheritance for the first six kids. His new wife never read the will and basically kept everything.
Karma would come back to her big time, though—his new wife ended up gaining 350 pounds. She now has MS and is unable to get out of bed.
38. The Tuition Fees…
My sister, who was 18 at the time, had a relationship with a man older than my dad for seven years. He already had several children older than my sister, and he was not in contact with him when the relationship started. He was so mean too, and my sister stayed with him until her friend pointed out to her that she was being too accommodating to him. Now she’s doing much better, and she got a pretty good deal out of the whole experience—I mean, the old dude did put her through pharmacy school...
39. Difficult Translations
My dad dated a woman six months older than me. My parents divorced about 20 years ago, but I found out through my brother that my dad, in his late 60s, was dating a 23-year-old. The thing is, she doesn't speak English, only Spanish. And he doesn't speak Spanish. They communicated through Google Translate. But whatever, I didn’t really care. He's happy, so I’m cool.
He died just over a year ago. My siblings and I hosted the wakes, and she came to the second one, dressed in terrible jeans and a big puffy jacket. She didn't come up to any of us and instead just sat there. Again, whatever; I'd never met her, so I didn't care too much...until the next day, just before we left to drive to the cemetery. That's when I lost it.
The priest was about to give the eulogy and asked that we all sit down. Before any of his kids could even move, she took the very front row with her relatives. Sorry, but you definitely should have waited to see if any of his kids, grandkids, or siblings wanted to sit there before you. It's not like they dated for many years or were engaged.
40. The Cool Grandma
My dad has a stepmom who is younger than he is. I don't know a lot about it, but his biological mom–my grandmother–did the whole “I'm an empowered feminist and freeing myself from my husband” thing, basically ditching him to go off and live on her own. This happened all while my dad was a teenager. It was a few years before my granddad met his new wife.
The age gap is pretty crazy—I think she was about 19 when she met my granddad, and my dad was about 20 or 21, but he's come out alright. My granddad’s new wife ended up having three children with him, and the youngest is just a year older than me. We all get along really well now. I guess we noticed when we were young that our stepgrandmother was more or less my mom’s age, but it didn't faze us.
41. The Gaming Buddy
I was around 21 at the time and a junior in college. My parents had separated for the fourth time. I headed to my mom’s house one weekend to surprise her, and I found a young guy, about nineteen, there with her. Apparently, they met playing World of Warcraft and my mom flew him to our home city in West Michigan. He was from Canada somewhere.
They dated for a year before my parents eventually got back together. It was horrible. So awkward, and he kept wanting to be my friend. I was pretty mean to him, but he wasn't all that bad.
42. Older Guys
My folks have been together for 31 years now. However, I’m dating someone their age. I have no siblings, and the guy I date has no kids. There’s a bit of an age difference between us, but my folks were probably ready for that. You see, I told them a long time ago that I was gay and that I’m specifically into older guys. Then, one day, I just came home with an older guy and they weren't surprised one bit.
Before that, I lived with an old guy and his son, a friend from college. I wanted to move out of the house, so I moved in with him. It was probably good practice for my folks’ state of mind! I’m in a significantly healthier relationship than that friendship ever was. We’re good together, and my parents like him. We live together now and we go out all over the place on the weekends. It’s just been awesome. There’s not much to say about it unless anyone ever asks.
43. Changing For The Better
My fiancé’s father is 65, his wife is 31, and their son is two. My fiancé is 36 and I'm 32. So, she's younger than both of us. Their son Nick is about as cute as cute can be and they seem happy. What was really a shock about his new wife is that she's Jamaican and has dreads, but my father-in-law is as white as snow. For context, when I first met him 10 years ago, he struck me as lightly racist and sexist.
Interestingly, his racism is now totally gone—the last time they were over, they were talking about him wearing a dashiki to watch Black Panther together. When they first started dating, they got each other black and white beaded bracelets. They said they were like tigers, half black and half white. They call Nick ‘Tiger’ now, but they say it's because that's her grandfather's name.
I don't believe it. My fiancé’s nieces and nephews, who are all now in their teens, call Nick their ‘buncle,’ which is short for baby uncle. When we go out, we get lots of confused looks. But honestly, it's all a fun dynamic. My man, on the other hand, had a hard time at first. Now, he just loves getting to be a dad, brother, and friend all at the same time.
44. Happier Times
I was just about 31 or 32 when my mom introduced me to her new boyfriend. She was 50 then, and he was maybe 25. At first, I was pretty weirded out. The thought of some young dude being with your mom can be...offputting. But as the years went by, I had a change of heart—it became clear that they cared for each other very deeply. My mom, who had always struggled with relationships since my dad left when I was two, was happier than I had ever seen her.
I got to know the guy, and he turned out to be pretty great! He was an Afghan vet; kind of a goof and not real smart, but absolutely a heart of gold. I wouldn't say we ever really got along, but we were friendly. They recently split up after six years, which has been a drag to watch. My mom's parents both passed away, which threw her for a loop, and she started pushing him away really hard.
I think that as she started feeling older, she didn't want to deprive the guy of the possibility of having a family of his own.
45. A Surprising New Friend!
My father moved overseas for work when I was in college, and during my first time visiting him, he waited until I was out there to drop the most shocking news of my life—he told me he was seeing someone “kind of young.” At the time, he said she was in her mid-twenties, so close to my age, but still older. That was already really weird for me. My initial assumption, given her age, was that she was after him for money or US citizenship.
That’s the stereotype, after all, and I wasn’t sure what else a girl that young would want with my fully American father. Their language barrier was significant, as were their cultural differences. I was quick to discover two things: first, she was actually only 19, nearly a year younger than me. Second, and possibly more surprising...we got along really well.
We’re peers now. While my dad was at work all day, we’d hang out with her friends, go grocery shopping, and cook dinner while watching Chinese soap operas. It was great! I still don’t understand the relationship AT ALL. But at least I can appreciate the friendship we have since our closeness in age gives us a lot more in common than most people have with a parent’s significant other.
46. Out And Having Fun
I never married anybody older than me, but I find older men attractive and I have been with quite a few of them in my 20s. For context, at the time I had a good job and I was successful myself, so I wasn’t looking for a handout. I’m also gay and I assumed older gay men are a lot more eligible than older straight men, so I didn’t really meet any creeps.
I'll never forget the nicest old man I've been with—he's now in his 60s and he has children 10 years older than me. I would have seen him more, but he had some health issues which made getting around kind of hard.
47. A Beautiful Connection
My mom passed suddenly when I was 16. My parents had four kids, my mom was the love of my dad's life, so he was completely devastated. The only thing that kept him going afterward was us. He lived in a depression for a very long time, and for 15 or so years, he was always putting us above himself. Finally, my dad and a girl he worked with found a connection.
She is younger than my youngest sister. My dad was 65 and she was 28 when they met. We did not trust her, but she proved us all wrong—they have been married now for five years. The truth is, my dad was poor and retired living on social security, so this was not a case of a gold digger. They truly loved each other. Last week, my dad passed while fighting heart failure.
He was 70 and she 33. She was by his side the whole time taking care of him as best she could. My dad told me he hoped I could find someone to love me half as much as she loved him. Our friends describe him as the dad everyone wishes they had.
48. In Sickness And In Health
My dad is 65 and he's in a relationship with someone who's eight years younger than I am. I'm 34, for reference. They've been together for three years and I'm happy for them. At first, it was a bit awkward for me, to the point that it took me a half year before I decided to meet them together. I was mainly worried about my dad, and for good reason—he came out of a long relationship that went really bad, and he had a really rough time with it.
I was scared he would end up in the same depression if this one went bad as well. I've spoken openly about my worries with my dad a few times, and it will take time for them to actually go away. There's a 38-year age gap, and my dad, at some point, will get health issues because of his age. I'm cautious of what will happen.
Both of them assure me they love each other and that they'll take care of each other, no matter what. I fully believe they love each other; that's very apparent from the way they interact. And I'm very happy they feel that way with each other and found that happiness. But I'll always be worried that when the health issues start—someone will have to do the day-to-day care, and that brings a lot of strain on a relationship.
It happens even to couples who've been together for 30+ years and are roughly the same age. In this case, they'd potentially be together for less than 10 years when it starts. I’m happy they’re happy, but I am cautiously optimistic for the future.
49. Younger And Younger
My father is an irresponsible creep. It was just the two of us when I was growing up, but he made it clear that he resented having to take care of me on his own. He's now in his 60s, whereas I'm 34 years old. His current wife is around 30 years old, but that's not even the most shocking part—she's actually the oldest wife he's ever had!
His last wife was 19 when they met, but even that was better than his girlfriend before that, who was a few months younger than me when I was 17. I always make sure that his wives know that I'll always be there for them and their kids when he leaves, because he's GOING to leave. It's interesting watching how surprised they are when he does.
50. Aunts And Uncles
When I was 19, my mom found out that my dad, who was 46 at the time, had been cheating on her again. The way she found out was horrible—she had found lewd pictures of him with his new girlfriend. My parents separated and my dad moved back to Vietnam. After a few years, I accidentally found out that the woman he was cheating with was a year younger than me, a fact that completely grossed me out especially considering that they met when she was 17.
I refused to meet her at first when I came to visit him the first time, but I later realized that was pointless and petty. They now have a 10-year-old and an 8-year-old. The worst part is that Vietnamese custom dictates that I refer to her as my elder and myself as a child. My kids also have to call their kids their aunts and uncles.
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