For a simple yes or no question, a proposal is one of the hardest questions someone will ever ask. It's also one of the hardest questions someone will ever have to answer. For these people, "will you marry me?" required way more than a simple "yes." From rejections and betrayals to delays and heartrending reunions, these stories kept us guessing until the end!
1. Push Through
I proposed and was engaged for like two months when out of the blue I got a horrible "gift" in the mail. It was my ring returned in a paper bag with very little explanation of what went wrong. It was horrible right after, like, I couldn't stop thinking about it every second. But it's been over a decade now and it was the best thing that's ever happened to me.
We were so, so wrong for each other and it was a toxic relationship. You can't see it until you've had some time outside of it to reflect and to meet someone you get along with so well you wonder why you didn't meet them earlier.
2. It Was Fine in Theory
We met through family and I asked her to marry me in a romantic video I made. She said she would think about it, then proceeded to ignore me for two weeks before telling me she just didn't feel ready but wanted to stay friends. But that's not even the craziest part. She brought up marriage all the time before I proposed! I’m happy we never got married!
3. Ending on a High Note
My mum actually said no to my dad’s proposal when they were younger—twice. Not because they weren’t in love, but because she wasn’t sure if it was something she actually wanted to do, rather than something that society expected of her, or whatever. They still stayed together and had kids—hence why you’re reading this now!
It wasn’t until my dad became terminally ill a few years ago that my mum decided it was now or never, plucked up the courage and asked him to marry her. However, my dad never forgot the two times she rejected him, so he returned the favor and said no—only to take her up on her offer a few days later. He passed away a happy man.
4. The Worst Reaction
My friend had been with his girlfriend for years, so he decided he wanted to propose. When he popped the question, she freaked out and said no. Over the next week, she freaked out more and more, and refused to answer his calls or messages. He then decided to use the money he had saved up for the wedding to buy a plane ticket to Europe. What was supposed to be a three month trip through Western Europe turned out to be a year long trip around the world.
But the whole time, he didn't know about one crucial detail. His girlfriend said no because she was also thinking about proposing to him. She'd already planned her proposal and bought a ring. She said no because she felt flustered and didn't want to give up her plan. That was a HUGE mistake.
One day, he says that he's coming back and she decides to go and wait for him at the airport and propose to him there. It turns out that while he was in Peru, he met a girl and they fell in love almost immediately, and got married in Peru. Cue five years later, he is still happily married to his Peruvian wife and recently had a baby, while his ex still hasn’t quite forgiven herself for ruining her relationship with him.
5. All That Work
I proposed and got rejected by my ex-boyfriend of five years. We started dating at 16 years old, and after five years I decided I was ready to take our relationship to the next step. Since we discussed marriage possibilities a lot beforehand, I knew he wanted to get married but wanted me to propose to him. So, I planned the perfect way to ask him to marry me.
I bought the rings then planned and payed for a two day kayak and camping trip so that the two of us would be alone. We rented some camping gear and went on our merry way. After setting up out tent and having dinner at the end of the first day, I decided to pop the question in front of the campfire. The first thing he asked me was if I was joking.
I said no. He asked if I was for real. I said yes. Then he said that he wasn't ready for this kind of thing and that he was "just a kid." I cried a lot. He didn't even want to see the rings I chose for us. We had an awkward end of our trip, then went back home. We were together for a year after that, but things were different.
The fact that he rejected me made me more aware that he was, in fact, still a kid, and I didn't want that at this stage of my life, so I ended the relationship. I've been single for almost a year now, and I honestly feel better. I grew so much as a person in that year and I'm happy he found someone else who is more to his pace.
6. Coping Mechanism
I knew a guy who proposed to his then girlfriend in a restaurant. He made sure to have a friend record it to get the big moment on tape. Oh boy, if only he knew what he was in for. After he asked, the girl walked out when he popped the question and pretty much ghosted him. He started drinking, found a new "passion" in gambling and gambled all his savings away.
He ended up living on money of the state but works as a garbage picker now and almost set his house on fire at least four times—that I know of—by making food and falling asleep after a few too many drinks. He is an interesting guy, friendly to some, but the state he is in is just sad.
7. Good Advice
My dad proposed to his then girlfriend at the time and she said no, as he had a drinking problem and she said she didn’t want to marry him unless he got clean. It took him a little while, and during that time the relationship ended, but he ultimately got sober. He wound up meeting my mom later through a match maker and they’ve been married for 25 years.
If the previous girlfriend had never said no to him, he never would have gotten clean. It was the lowest point in his life, but it all brought him to my mom, who makes him happier than ever. My dad remains in contact with the ex-girlfriend and talks to her from time to time. She also got married and had a son.
8. Lasting Effects
I was the one who said no to the proposal. We were high school sweethearts who had actually known each other since first grade, and despite me moving to a different city during elementary school, we reconnected in high school. I followed him out to college and realized there was a whole other world out there besides the small towns I grew up in.
He already had our entire life planned out and it wasn’t until we had dated for three and a half years and he “surprised” me with a ring and a proposal that I realized he wasn’t what I wanted at all. He was lazy, never went to class, didn’t stand up for himself, and was codependent. So, I said no. It was awkward, but then it got so much worse. He proceeded to literally stalk me.
We lived in the same apartment complex, but different units. He would knock on my door at all hours of the day. I never answered. He would call and text constantly—this was before you could block numbers on an iPhone. He broke into my roommate’s unlocked window. I wasn’t at the apartment, thank God, and he told her, “I was just trying to get some stuff." Yeah, right. On the very rare occasion that I would open the door, he'd force his way in. I called the authorities numerous times but they never did anything.
At one point, he somehow knew information that he COULDN’T have known unless he had somehow installed a program onto my computer. Eventually, he backed off a little, however, TO THIS DAY, I still hear from him. I’m married now, for almost four years, and I’ve heard that he is also married and has a kid on the way. Even that didn't stop him.
A few months ago, he found my extremely obscure Facebook. I have maybe 11 “friends” on there and he has no connection to any of them. Anyway, he asked me to meet up with him for lunch for closure.
I blocked him, but I know I’ll hear from him again somehow in a few months. It’s ridiculous, honestly. I regret ever dating the guy.
9. Missed the Cut Off
We talked about getting married and agreed that so long as the proposal was a surprise it would be fine. So, I got help from some of her friends to make it special. Dinner at her favorite restaurant with our families in attendance and the ring on a piece of chocolate cake delivered by the waiter. The act was, "we just all happened to show up at the same place on the same day at the same time."
Sure, a child could see that it was a setup, but that wasn't the point. The evening goes great, the cake comes out, the ring is discovered, I get down on one knee…and she says no in front of everyone. My family is shocked and her family is shocked. Her friends are, for some reason, not so shocked. She breaks up with me right there and tells me that the reason she said no was because, "You took too long." I didn’t realize I was on a time limit. A month later, she's engaged to one of her co-workers.
10. Gone Forever
I proposed to my then girlfriend and she said no. She then told me she needed to leave and think about what just transpired. I never heard from her again.
11. Don’t Look at That!
In 2017, Google came up with this program that allowed you to make photobooks out of your Google photos account. My girlfriend and I had been dating for almost two years and I knew she was the one I wanted to marry, so I created this wonderful photobook of all of our selfies together and ended it with a photo captioned, “Will you marry me?”
I then proceeded to put all these things into an album and build the photobook. Though I didn't realize it, I was making a huge mistake. I put the pictures in a shared album, where the other person gets a notification when you add new photos to it. Sure enough, the other person the album was shared with was...my girlfriend.
That evening, we had dinner and it all came out. She saw the photo and told me she wasn't ready. There were a few reasons why but they were good reasons and smart reasons, as they mostly had to do with timing, family, and finances. We weren't breaking up—we just weren't getting engaged. A year later, we talked about it again and went out to buy a ring.
We celebrated our first wedding anniversary in April. And for those wondering, the photo book is on a shelf to my left as we speak.
12. Driving Force
My mom and dad were not yet married but wanted a kid and eventually had me. However, my dad is Catholic and Hispanic, so he wanted to be married to my mom if they were going to have a family together and proposed. She said no because she hadn’t been divorced from her first husband for very long and wasn’t ready to get remarried.
He responded with a chilling gesture. He threatened to leave her, then got on his motorcycle and started to drive away. It worked, as my mom chased him down and accepted his proposal. They wasted no time in getting married, as they immediately flipped through a phone book and looked for someone who would marry them for free that same day.
They eventually came across a small mom and pop shop/restaurant in a bad part of town that agreed to do it in their backroom using their staff as witnesses. It was a quick five minute ceremony that ended with the officiant making them eat a meal with them. To their dismay, they were charged for all of it and had to run home to break open the quarter jar.
13. Slow Swimmers
My mom told my dad no when he proposed to her, even though they were already living together. Her reason for the rejection was that she thought he was infertile—but then she got pregnant, so her no turned to a yes. In retrospect, I wish my parents had decided early in their relationship not to get married, as they can barely stand each other these days.
14. The Harder the Struggle
I proposed and she said yes, but one month before the wedding she took it back. This is what happened immediately with my life. I personally lost about $3,000 worth of deposits. My parents and her parents lost about $4,000 each on deposits. My parents and I are working class, so it took us years to recover financially from this.
I also spent $2,200 on a ring, but that's not even the worst part. The store where I got the ring wouldn't take it back. I took it to pawn shops and they'd only offer a few hundred dollars. I locked myself in my room and didn’t take any calls. I just stayed in bed, until my roommate grabbed me and took me to the ER, where the doctor treated me for severe dehydration and an infection.
10 years later, I know that this experience made me stronger. I met another woman and we've been married for 13 years now. She's my best friend. Whether I have good news or bad news, she the first person I want to tell it too. I learned my lesson about the engagement ring, too. I only paid $300 for it and she LOVES it and treasures it to this day.
15. Time to Think
I had two friends who both had terrible upbringings but found each other and started dating at 14. Then sometime in their early 20s he proposed to her but she said she wasn't ready to commit yet. After that, he began proposing to her every year, partially because he hoped she was ready but at the same time it had become kind of a ritual, as he would show her that he was still serious.
She said no every time, until late in their 20s when he finished his studies and she could see the finish line. She told him she was ready—meaning marriage and eventually children—but then everything changed. He got second thoughts about marrying the only woman he ever had a relationship with, as he was no longer sure it was the right move.
They took a break, during which she went to the US—from Europe—to do her PhD at MIT. They drifted apart more as she moved on and found a new long term relationship with a partner that's a lot better for her, while he quickly regretted ending the relationship, and has yet to find someone half as good as she was.
16. It Happens
She said yes on the second proposal and now we're divorced.
17. Caught Off Guard
I spoke to her about marriage beforehand, and she seemed really keen on the idea. So, I decided to propose about a week after in front of all our friends and she was so shocked she picked me up off my knee and shooed me away. Most of our friends were confused because everyone knew it was going to happen, and she said she was excited for it.
I didn't know what to do or say as it was all really embarrassing. Thankfully, she explained to me that she didn't mean no, she just didn't know what to say and got scared. After we cleared that up, she apologized profusely before finally saying yes! I’m proud to announce that this year we celebrated our nine year anniversary.
18. Paw-posal
My mom rejected my father the first two times. There were no hard feelings between them. I guess my mother just wasn't ready for marriage yet. When she finally was ready, she decided to propose to him. My grandmother and mother sewed a suit for their dog to wear and attached a sign around his neck with a ring that read, "Will you marry me?"
Then, she sent the dog out into the kitchen to beg for scraps while my father was preparing dinner. The next thing she heard was a very concerned voice shouting, "HONEY! The dog is asking me to marry him!" Cue absolute hysterics. My dad said yes to the proposal, and my HUMAN dad and my HUMAN mom are still married two decades later.
19. Helping Hand
We'd been dating for a year and a half when I was due to move out on orders, as I was in the Army. She suggested we get married and I said no way, as I was going off to school for six months, then a year on deployment to the Middle East. It just wouldn't work. She was calm, and then said, "You think I'll be a burden to all of that, but I'll actually be a help".
While just seconds earlier all I could think of was what a pain it would be to get married and leave, now it—for whatever reason—seemed perfectly reasonable that she was right. We got married a week later at the courthouse, and last month we had a nice socially distant dinner party for our 29 year anniversary with our two amazing kids and a few friends.
20. Language Barrier
We received a letter from the immigration office saying that she was lacking some documents. At the time, we were both stressed with work and study, and none of us were sufficiently fluent in German to decipher this kind of language. We went to the university office for help. Unfortunately, the lady in charge did a poor job translating the letter as she told us it stated that even with the proper documents they would proceed with the deportation process anyway.
We immediately began to panic, and ended up at City Hall looking for some help. With adrenaline rushing through me, I asked the poor guy at the information office, “If we get married, could we stop the deportation?” I can't remember if he gave us an answer, but regardless I yelled, “I want to marry her!” The turned to my girlfriend and yelled, “Will you marry me?”
She started laughing. I started laughing. The guy in the office gave us the telephone number to the pertinent department and told us to call. The second we stepped out of City Hall we couldn't stop laughing. She said, “well, thank you, but let's wait a bit.” After the weekend, we went to the immigration office and the people there explained which documents were missing and how to get them. She wasn't denied the visa and we kept living in the way we planned.
We still live together and thankfully, she got a job that provided her with a visa. Soon she will write her citizenship exam. Fingers crossed that she passes!
21. Let’s Not and Say We Did
She had mentioned that she wasn't really a fan of marriage, but I wanted us to be together for the rest of our lives so I thought proposing non-marriage might be well received. I asked her NOT to marry me, and she said no. We have been married for 10 years. I guess there really is some truth to reverse psychology.
22. Hindsight
I had planned a special occasion for my proposal. Before we went to a family event, I took her on one of those observation wheels and I proposed at the very top with a ring I had designed myself. I was overjoyed when she said yes—at first. A few days later she exchanged that yes for a no, and my whole life fell apart.
I was distraught, but we pushed past it and continued dating for a while, albeit long distance. When I would visit her, it would get super awkward, and eventually her dad no longer let me see her. It took me years to recover from the whole ordeal. Now, I am happily married and looking back I am glad the previous relationship never worked out. I was not in a good place when I met her, and her family were super controlling, so it would never have worked. The woman I married is super cool and is my best friend, so everything turned out better than expected.
23. Food for Thought
My dad kept proposing to my mom and was eventually successful when he stopped using onion rings.
24. Pays to Listen
We had only known each other for three months when he proposed. He was smitten but I was more cautious. I told him no, I like you but it's way too soon. He asked how long he should wait before asking again and I said maybe a year. He proposed again at midnight, exactly one year after we first met. I said yes, and we have been together for eight years now.
25. Worth the Wait
I had a friend who was getting over an awful past relationship. As we hung out and spent time together, I realized that I had fallen in love with her. She was the only one who, despite suffering from depression, helped me out of my social anxiety. I just couldn't see her suffer anymore. So I proposed to her...and got rejected, as she wasn't ready to be in another relationship.
On top of that, since I confessed my love, she got more anxious and our friendship was temporarily over. We didn't talk or stay in contact for months. Later on, I decided to contact her to see how she was doing and learned that she was shutting herself in her room and minimizing contact with people.
I still had romantic feelings for her, but I wanted to be there for her to help her move on, so I insisted on being friends again. We spent our time like that, and honestly, she's the only friend I had. Time passed, and when I saw she was getting back to her normal life, I proposed to her again, and she accepted. I have never been happier in my life.
26. Earn It
My mom and dad had been dating for a few months when my mom proposed to my dad. He said no, not because he was a traditionalist but because he didn’t want to marry her until he could get a proper job so he could provide for her. A month later, he secured a job, and they got engaged. They celebrated 32 years of marriage last month!
27. General Analysis
After my proposal was rejected, life got bad for a while. Then it was REALLY bad. Then it became really bad. Then it became bad. Then it was just blah. Then it was neutral. Then things started to get better. They continued to get better by me learning to be happy and me doing things for me. I eventually found someone else, and things have been getting better for 20 years now.
28. Learning From Mistakes
I proposed to my very first girlfriend ever and was rejected. We started dating at 17 and after six years of dating I proposed. She said, "No, I'm sorry." I asked why, and she said, "I've been thinking about this for a while but didn't talk to you about it. I found someone else." Then she broke up with me right then and there.
I asked if she cheated and she said no. "We're just friends right now. But he makes me happy when I'm with him and you just…don't. You used to. But not anymore." I tried sabotaging their relationship when I found him begging her for inappropriate pictures, tattled to her ultra-Christian parents that he was twice her age—which he is—and did everything I could to be the insane one.
I finally realized what I was doing, apologized, and promised to never talk to her or her family ever again. I sold the ring and used the money to buy a guitar and a boatload of weed and spiraled out of control for three years. I flunked all my classes, got a dead-end job at a construction gig, and slowly descended into borderline alcoholism.
I couldn't leave the house or go to work or do my job without being high. I gained a ton of weight and let myself go. Finally, I contemplated suicide and planned it out with a 20-page instruction manual on how to make it painless, not screw it up, and not hurt anyone in the process. I never went through with it because I kept getting scared.
I eventually broke down, told my parents all of this and asked for help. I spent another year in a rehab program with a therapist, got out and have been clean for three years this September. I still wake up at 3 AM feeling sick every couple of months for the way I treated my ex, after having spent six years telling her that I loved her.
But, that's all over now, and all I can do is learn from it, promise to be better, and keep going. I'm turning 29 in a week, still living at home with my parents, and constantly battling self-loathing and anxiety while working a job for $9.25 an hour. But I pay my parents $300 a month to stay with them and I'm going back to school.
29. One Last Shot
I dated my current wife in high school, but I was all wrong for her at the time. It was going way too fast so we broke up, but on good terms. One of the last times we talked, I asked her if she would marry me one day. She laughed it off and said no way, as I was definitely not the marrying type. Fast forward to college. I was working full time and she was a law student.
She walked into the store I was managing and we immediately reconnected. We talked for an hour, and it spilled into the parking lot as we were just talking and catching up. At the end of the conversation as she was leaving, I jokingly asked her to marry me again. She laughed, I laughed, and she said, "we'll see." We’ve been married for 16 years come October.
30. On to the Next One
I asked my girlfriend after almost six years together if she would marry me. She said no and added that maybe it was time for us to go our separate ways. Wow. I was shocked, but life must go on. About a year later, I met a different girl and we were engaged within a year. We were both ready for marriage. That was 16 years ago.
We’ve got three terrific kids, two boys that are exceptional athletes and a girl who’s a brainy little nerd. The lady who refused me eventually got married, had a couple kids, and got divorced. But she got married again and had another kid—and then got divorced again. We completely lost touch several years ago.
31. Great Minds Think Alike
We were living together at the time and I asked her to marry me. She said, "No, I love you, but I need to think about it. I don't think I'm ready yet. Can you give me some time and ask later?" A few months go by before I ask again and unfortunately get the same response. A few more months, same question and same answer.
Then, a couple weeks later she says to me, "Hey, what do you think of us getting married?" I replied, “That's an excellent idea, why didn't I think of that? Our 39 year anniversary is next month.
32. Healthy Distraction
My first major girlfriend was stunning. She modeled and I was completely besotted with her. Well, she started slipping away and I thought it’d be a great idea to propose to her so that way she’d be with me forever. Thankfully she was too smart for my desperation and turned me down flat, telling me upfront that she was too young to settle down.
Losing her was more traumatic than being turned down and I struggled with despair for a while until I channeled myself into my career, which took off. A few years later, I found my true love and it was her that proposed to me. 26 years later and we are still happy. As for my ex, I bore her no ill will and can only thank her for being smart enough to know that we were never destined to be together.
33. Risky Joke
I asked my wife to marry me but she knew it was coming so she had some fun with it. I got down on one knee and she said no. I went pale, but then she said, "just kidding, I swear!" We’ve been married 22 years last April, and every once in a while, just for fun, I bring up how she initially rejected me, and she always apologizes.
34. Finish That Thought
I proposed to my wife in Central Park back in 2013. We were with her sister and her sister’s fiancé, and they were in on my plans to surprise her. They juggled around the ring box, he took random photos of squirrels, or whatever, to justify him carrying his nice camera that day, and just otherwise being very supportive and helpful.
When we got to the little bridge that we usually took pictures on, we did our pose and I did the classic, “oh shoot, I gotta tie my shoes real fast” move to get down on one knee. I busted out the ring box and popped the question. She had no clue how to react and uttered a soft but very clear, “…no…” You got to be kidding me!
Thankfully, she was just speechless and stunned that I was able to pull the wool over her eyes all day and the “no” was more of a “no way you were able to do this” reaction. Honestly, even I was surprised I was able to pull it off without a hitch. We’ve been married for almost five years now and have twin daughters!
35. Tattletale
My first marriage proposal happened when I was in the second grade. The girl’s name was Christina and she was in my class. I asked her if she would marry me and she said no. I didn’t handle the rejection well and I did the only reasonable thing a child in the second grade would do—I told the teacher on her.
36. School Comes First
She was an Art Major and I had just joined the Army. We had been together since high school so I asked her to marry me, and she said no. Her reasoning was that she wanted to get her Masters first. We were friends for a while, but ultimately broke up and haven’t talked since. I believe she works as a bartender now. I ended up getting married to my best friend instead. We’ve been married for more than a decade and have a five-year-old son.
37. Keep It Local
We met in her home country of Germany while I was traveling. It was love at first site and we dated long distance for a while, with either me flying to Europe or her flying to the US. After a while, I suggested marriage multiple times so we could justify living together in one place. Her answer was always the same—no. I stayed patient and tried not to be pushy, as I knew she was worth the wait.
Then finally one day it hit her—marriage is how we could be together. If we got married, we could live in a country together. A few years later and I'm still married to my best friend and living with her in Germany.
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38. Heads Up
After I proposed the first time, she said no, but we continued living together for another six years until she changed her mind and told me that I should ask again. I did, and she said yes. We were engaged for over a year and got married in 1991. We are still married, have three children, and are still very much in love to this day.
39. Spread the Word
My mother told my father no three times. On the third time, he got wasted at a local bar and basically started pouring his heart out to anyone who’d listen. Mind you, it’s a very small village in the Italian alps and my father barely spoke Italian, while no one in the village spoke English, including my mother. Well, word eventually got back to my mom about this sad American at the bar, so she went to find him. My parents celebrated their 44 year anniversary last month.
40. Fortune Teller
We had only been dating for about six weeks, but I knew, I just knew she was the one. She said, "You're a great guy and I love you, but I'm not ready to get married." We continued dating, then I asked again a week or so later and got a similar response. Lather, rinse, repeat. I asked four more times over the next few weeks.
Then one day, we were at a Chinese restaurant when the fortune cookies come. When we opened them, our jaws dropped. Mine says, "Your wish is within reach. Ask once more." Hers says, "Get your hope chest ready." No lie. No setup. They were totally random cookies from the restaurant. I reached across the table, took her hand and asked for the seventh time.
She didn't really say, "Yes", but gave more of like a sigh and a resigned, "Okay." Our first date was on December 12, 1981 and we got married on April 3, 1982. We’re still together today and have one son, two granddaughters and two great granddaughters. I’m still giddily in love. Never give up! Never surrender!
41. Taking a Break
I told my now wife the second day we were talking that I was going to marry her. Her response was, “I’ll NEVER get married again.” We dated for around six months before she dumped me, seemingly out of nowhere. We were broken up for nearly six months before I unblocked her number and unblocked her on social media.
When we met up again in person, I gave her the biggest hug and kiss and just couldn’t believe she was back. After tons of long talks and building our relationship back together and WAY stronger, we got engaged. I married her, and we’re happier and stronger than ever. I’m so glad it worked out this way. I love her more than I thought possible.
42. I Quit!
My mom turned down my dad multiple times but said she’d reconsider if he quit smoking. They’ve now been married 47 years and my dad hasn’t smoked since!
43. Taking the Initiative
My dad asked my mom to marry him several times and she kept saying no. She had been engaged before and it was a disaster of a relationship, so she had decided she was never going to get married. My dad seemingly accepted her reasoning, they moved past it and decided to stay together. That is, until one day...
My dad says, “sit down, we need to find a day that works where both our families can be in town for our wedding.” My mom was like, “okay”, and they got married. She loves that story but he just rolls his eyes and goes, “your mother is SO difficult.” They’ve been together for 32 years!
44. Calling His Bluff
My grandfather proposed to my grandmother on the fourth sentence he ever said to her. She laughed, thought he was crazy, and said no. Then she told him if he was legitimately serious, to meet her the next day. He did, and she said yes. They shared 67 incredible years, incredible stories and an incredible life together.
45. Funeral Crashers
Back in the 60s my father proposed to his high school sweetheart shortly before he graduated. She was a year behind him—only 16 at the time—and made the much more mature decision of answering “not now, I’m only 16!” But all he heard was “no”, and after a few months of fighting, he broke things off with her.
He met my mother a little while after he graduated, and they got married. They were together for 43 years and had three children before she passed in 2009. In 2017, my father reconnected with his old high school girlfriend at a funeral—as 70-year-old’s apparently do—and they have started dating again.
We—his kids—all really like her and are happy that he’s not alone and has companionship. I asked if he thought he’d ever remarry, but he said that he had a wife, and would be buried with her. I am so lucky to have had their relationship as the anchor of my childhood and look up to them as role models in my own relationships.
46. She Said What?
My dad asked my mom to marry him several times, and she said no several times, until one day when he asked and she finally said YES! Exciting, right? Not really, as this caught him off guard, causing him to freak out, dump her, and leave her apartment. Three weeks later, he realized he hated his life without her, so he begged her to take him back and marry him.
They ended up getting married nine months later and stayed together for 16 years until my mom passed from cancer. They loved each other so much and had such a deep appreciation for each other. That was 25 years ago, and my dad has yet to remarry. No one will ever come close to my mama.
47. Puppy Love
My ex's parents have a cute story. They both grew up poor in nowhere, Texas. They start dating and he makes it big in the banking sector, like really big. He buys a ring and takes her out on a date and pops the question. She says no. He buys her a car and surprises her with it and pops the question again, and she says no again.
A week later, he shows up with a puppy in his coat pocket and she can't resist the puppy dog eyes—literally. They've been married some 35 years now, I think.
48. Committing to a Bit
My dad proposed to my mom after they'd been seeing each other for just under two weeks. It wasn’t really a serious thing where he got down on one knee, though. My mom and dad were planning their next date and trying to figure out if they could go do anything after he got off work. He said, "Hey! I know! We could go get married!"
He was serious but he framed it as a joke because he knew it was insane. She laughed and basically told him he was crazy, that it was way too soon. My dad said jokingly, and he is very proud of this fact, "Fine. I asked you once. I'm not gonna ask again." My mom thought he was bluffing.
After a year of dating she started giving him a hard time about not asking her to get married again, and he stuck to his guns and said she missed her chance and he wasn't going to ask again. My mom finally broke down and asked him to marry her. She made sure she properly mocked him when she did it, too.
She made a big show about asking his father for permission, got down on one knee in public, and got him the gaudiest engagement ring she could find. He said yes and they just celebrated their 30 year anniversary.
49. Misread the Situation
We were only dating for a little over a year but I was certain she was the one. I drove two hours to see her at her college and we went on a beautiful winter night walk where I proposed. She looks me right in the eyes and says the most heartbreaking thing I've ever heard: “Oh, you thought this was serious? Well I don’t know how to say this other than I have been seeing other people. Well actually I have been seeing other women.”
I was stunned. I got up, put the ring in my pocket, walked to my car, got in and drove away, never looking back and crying the whole time. I haven’t seen or spoken to her in seven years, even though she has tried countless times to reach out. Now it’s a story I tell friends who are nervous about asking their significant others to marry them. Even if they say no, it couldn't be worse than what happened to me...
50. Better Now Than Later
I dated a woman for over two years before I finally decided to pop the question. The first time she said, “I don’t know.” A couple months later, I asked her again, and she said “maybe.” I was pretty bent out of shape, but then I found out the horrible reason why she turned me down. She was sleeping with several of my friends, so I guess I dodged a bullet there.
Sources: Reddit, ,
