Proposing to the love of one’s life should be a happy and romantic moment; one that should be remembered forever—but not for these unfortunate hopelessromantics. After much anxiety and planning, their dream proposals not only backfired but also took their souls with them. Others were greeted by downright cringe-worthy embarrassment. Just be thankful that these didn’t happen to you.
1. The Wait
So, I popped the question after seven months of dating but she turned me down, feeling it was a bit too early. I respected that and stowed the ring in a secure deposit box, reminding her it was ready and waiting if she ever changed her mind. I thought all hope was lost—until fate gave me a blessing.
I didn't know what to anticipate next, but later, she said yes! We resolved to have a lengthy engagement of two years to ensure we were making the right decision. Fast forward and today, we're celebrating 37 years of marriage.
2. Wake Up Call
We had been together for two years, and even though it wasn't all smooth sailing, I felt genuinely content.
After putting aside some money, I purchased an engagement ring and devoted an entire day to devising a proposal plan. When it was time, I got down on one knee and proposed. Her response was to laugh, yet she agreed. I was ecstatic. I brushed aside her laughter as maybe nerves or surprise, but I didn't really care—I was going to be a married man!
The subsequent morning, as I usually wake up first, I took our dog for a morning stroll. Upon getting back, I found her just about finishing a phone call. I asked her if she had shared our engagement news with anyone since we had decided to announce it jointly.
She shrugged it off, saying she needed a chat with someone and quickly dismissed it. I made a light-hearted comment that maybe she was talking to a secret lover. Suddenly, her cheerful demeanor changed, and I felt a sinking feeling in my heart.
She then admitted, in a calm and straightforward manner, that yes, she was indeed having an affair. She was leaving me, she announced, and she would start packing a bag. Three days passed, she packed all her belongings and left, like she had never been there at all.
It felt like she had ripped my soul apart and didn't have an ounce of remorse. To make things worse, she ended up marrying him. That was a hard pill to swallow.
It sent me spiraling into depression and led to excessive drinking. At that time, it felt very sudden, but looking back, I've always had a blind spot when it comes to judging women's character.
3. You Win
The first time my dad laid eyes on my mom, he asked her to marry him. That very night, they shared deep, meaningful conversations for hours on end. Even though marriage wasn't on his mind initially, something about her just felt right.
But she denied his proposal, not just once, but repeatedly, although she kept accepting his date invitations. This scenario repeated itself almost every day for half a year.
Then came the night they had their first Scrabble face-off. Scrabble's a big deal for my mom. She's the type who enjoys using her extensive vocabulary to outsmart everyone around her. She's like a living, breathing thesaurus.
However, that particular game didn't go as planned. For the first time she could recall, she lost. In defeat, my petite, 5-foot mom cleared the Scrabble board clean off the table, pieces scattering in all directions.
In her frustration, she turned to my dad and blurted out, "Alright, I'll marry you"! To which my dad, true to his nature, responded, "Hmm, I'll have to think about it".
But he didn't need much time. Within eight months of their first meeting, they exchanged vows in a quaint Vegas chapel. This year, they've been happily married for 23 years.
4. It Takes Balls
At the baseball match, he took the leap and popped the question on the jumbotron. The words of his proposal lit up the colossal screen, and moments later, the camera focused in on them. Watching this unfold, everyone felt a wave of secondhand embarrassment.
The lady chuckled, and suddenly the man's face dropped. As he drooped back into his chair, he looked like he was on the brink of tears just as the jumbotron switched off. The crowd reacted negatively, heaping boos onto the woman and even tossing trash in her direction. Stadium security had to step in to escort her out.
5. A Whole Lot Of Nothing
Once upon a time, my boyfriend and I went out for a pleasant stroll. I noticed he was a bit jittery and suddenly, he stopped. Gathering courage, he stuttered out, "I've been considering—the long-term...uh...advantages of—well, tying the knot—or something similar".
He confessed the ring was stashed in the car but improvised with his wallet as a symbolic ring box. Then, in the traditional manner, he got down on one knee and proposed. Thrilled, I said yes.
We walked back home, all the while he cautioned me to keep the news a secret. This secrecy hint should have been my first clue that not all was well, though his anxious and confused behavior wasn't out of the ordinary.
Returning to our apartment, dinner went by unusually quiet. Afterwards, slouched on our couch, he dropped his head into his hands and confessed, "I've made a terrible blunder".
Within thirty minutes, our newly minted engagement was over, so was our relationship. I took off on a long drive, showing up back home three hours later. After further conversations, we mutually decided to dial it back to simply dating.
Several months into this arrangement, he announced his desire to part ways permanently. When I inquired about his reasons, he stammered and then burst out: "We visited Target absurdly often. Plus, I wasn't in love with you".
We haven't communicated since then. We were a couple for nearly four years preceding the pseudo-proposal. Then, post-breakup, he disappeared abruptly.
So it was that in the span of one day, I had a boyfriend, became a fiance, turned into an ex-fiance and found myself with an ex-boyfriend. 
Africa Studio, Shutterstock
6. Would You Like Some Cake With That?
I've experienced a few declined marriage proposals in my time working at an upscale restaurant. The one that still sticks out to me involved a man who had the engagement ring delivered with dessert as a grand surprise.
The woman's reaction was of shock and clear frustration; she ended up saying no. A waiter nearby happened to hear her say, "You're not even my fourth or fifth choice".
It appears they hadn't been dating for long and he proposed out of the blue, catching her off-guard. 
George Rudy, Shutterstock
7. Let Me Think About It
She mentioned she needed time to consider the proposal. After a fortnight, I received an email from her all the way from Hawaii, unfortunately turning me down. 
tommaso79, Shutterstock
8. The Longest Wait
For three days, I holed up at home, toying with the idea of phoning her but never quite getting there. Eventually, I gathered up the courage to visit her house, though I was quite apprehensive. She was under the impression I had come to politely end things in person.
I ushered her into a seat and then proposed, taking her completely by surprise. Her response caught me off-guard: she asked for time to think, and those moments felt like an eternity to me.
Two weeks later, we found ourselves on what I believed would be our final date. She requested that I propose once more. So, I did. This time, she said "yes".
Fast forward forty-one years, we're blessed with three children and six grandkids. We've been business partners for two decades and honestly, she's my jackpot in the lottery of life.
I'm so grateful she challenged me to "Ask me again." 
Studio Romantic, Shutterstock
9. You Crashed My Party
My parents had a car accident once. Then just before my mom's X-ray, they performed a pregnancy test, revealing that she was pregnant with me. My dad swiftly proposed to her, right there, while still wearing his neck brace.
She declined, stating that she didn't want to wed just because she was expecting a baby. My dad broke into tears, explaining that he had intended to pop the question on Valentine's Day, and even had a ring ready.
A week afterwards, she said yes, and they've now been happily married for 22 years.
TranStudios Photography & Video, Pexels
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10. I Kid You Not
We were enjoying a meal at Ruby Tuesday when I popped the question. Instead of an immediate "yes", her response was, "Hold on—No. This can't be happening".
I had to persuade her that this was a genuine proposal. Not the highlight of my evening, for sure, but thank goodness, everything fell into place in the end. 
Scott Webb, Pexels
11. Where’s The Romance?
The story of my parents getting engaged is probably one of the least romantic ones ever. After just shy of five weeks of dating, my dad, ringless, casually asked my mom to marry him out of the blue. Amazingly, she said, "Yes."
Contrary to popular belief, this didn't take place beside some dreamy fountain or over a sophisticated meal – it was completely the opposite. My dad popped the question right there in his truck, just as he was about to drop her off after their date.
There was no bending on one knee, no shiny ring, and it seemed like he didn’t spend a whole lot of time planning this. But, she still said yes. Main plot twist—he called the next day to retract his proposal.
A few days roll by, and he changes his mind once again and ends up proposing for round two. Astonishingly, she still said yes. It's genuinely bewildering how a duo, with such a shambolic engagement journey, have stayed together for 26 years. Yet, they're still—to everyone's surprise—branded as "the cutest couple". 
sivilla, Shutterstock
12. Awkward Silence
I watched as a man got rejected at Universal Studios City Walk. The crowd around them was buzzing with excitement, cheering them on. But the cheer turned into an echoing silence—she ended up declining his offer. He pulled himself together, dusted off his knee, and they both left in a hurry. 
Dean Drobot, Shutterstock
13. Not A Surprising Outcome
I come from a typical Indian household, but I'm far from being traditional. To avoid any unwanted hullabaloo, I agreed when my folks suggested I attend a matchmaking event.
Once I arrived, I approached the first woman I noticed and popped the question right off the bat. Unfortunately, she wasn't on board. 
Deepak Khirodwala, Pexels
14. Just A Dream
I decided to pop the question to my girlfriend on an island in Boston Harbor, with the whole city as our backdrop. When she said yes, we spent the rest of that glorious day just enjoying each other. At night, back in our cozy, well-lit apartment, I found myself daydreaming about our future together—a shared home, kids, the works.
Fast forward three months, she confessed she had fallen for her soulmate, who happened to be a married man she had met during her internship. Despite my best efforts over the next three months—getting up early to prepare her breakfast and planning weekend date night—to show her how deeply I loved her, she still ended up choosing him. 
NAK Photographer, Shutterstock
15. This Isn’t A Dress Rehearsal
I act as the host for live stage events. Numerous times, I've been approached to facilitate proposals, but strangely, very few follow through. Roughly one in ten would-be stage proposers make it to the event. Almost all who do are met with a tearful 'yes', applause, and warm hugs and kisses.
There's one proposal that went south which I won't ever forget. It happened during a cosplay contest. I remember the guy dropping to a knee and making his proposal. The girl, taken aback, didn't utter a word, simply shook her head and ran off.
Then, the guy, dressed like a medieval bandit or Robin Hood, tried to regain his feet. But his boots were too high, or maybe he stepped on his cape. He toppled over. Eventually, he got up and made an exit.
The crowd fell silent. I was at a loss for words, so I just continued with the next contestant and acted as if nothing happened. Later, at the after-party, all the judges and staff couldn't stop talking about how cringeworthy the incident was. One judge confessed, "I almost keeled over from secondhand embarrassment." 
evrymmnt, Shutterstock
16. Not My Fairytale Ending
We'd been a couple for over eight years, and things seemed great. We often discussed careers, living arrangements, starting a family, and planning our future together. Rings had been shown, weddings discussed, and it felt like the right moment for a proposal.
So, I purchased a ring and began organizing special trips to create the perfect proposal scenario. In the end, I chose New Year's for the big event. But, just prior to this, she pulled away. It was too perfectly timed to be a coincidence, but she must have had an inkling. Her words pierced my heart: "I love you, but I'm not in love with you".
We attempted to keep a friendship alive post-breakup, but it proved challenging for me as I was still very much in love with her. Eventually, I had to distance myself completely for about a year, since we shared the same friends, and being around her was just too tough. This isn't where I thought I would be at this stage of my life. 
Prostock-studio, Shutterstock
17. What An Entrance
I'm employed in the international arrivals section of an airport, and each day I witness heartfelt reunions so packed with emotion, they're almost overwhelming. Can you tell I've been here a while?
One ordinary day at my spot, an unexpected sound of a trombone interrupted my peace. I've seen people strumming guitars, playing ukuleles and saxophones, and once even banging a drum set—but a trombone in international arrivals? That's a first!
The song kicked off and I soon identified it as the Imperial March from Star Wars. This left me utterly bewildered, looking around for the source of the music. I noticed a girl blushing furiously among the crowd, and figuring she must be involved in the peculiar event, I kept an eye on her.
Sure enough, she approached the trombone player. He finished his song, handed off his trombone to presumably a friend standing nearby, and then dropped to one knee.
Although the distance between us—about 25 feet—prevented me from hearing their conversation, I clearly saw the guy's smile transform into disappointment before he rose and trudged away, leaving the girl standing alone, her face as red as ever.
Well, that was an awkward situation to witness! 
Aquarius Studio, Shutterstock
18. You Stubborn Brute
Just shy of two weeks into dating, my dad popped the question to my mom. He was met with laughter and was called a little bit crazy—it was far too soon, according to her. My dad had a retort at the ready, and he's quite proud of it till date, "Alright, I asked once. I'm not going to do it again." My mom didn't take him seriously and assumed he was joking.
After a year of steady dating, she began to tease him about not proposing again. However, my dad was firm. He hadn't forgotten his initial vow. He told her she missed the boat and he was sticking to his word.
In the end, my mom was the one who ended up proposing. When she did, she made sure she had a little fun with it. She put on a grand display of asking his father for his blessing, she knelt down in a public place, and even bought a super flashy engagement ring. He said yes, and they recently marked three decades of wedded bliss. 
Ground Picture, Shutterstock
19. Kick In The Teeth
Just a day after I got the ring, and a day before I planned to propose, she rejected me preemptively. She confessed that she had doubts and was contemplating a move across the country. Sure enough, she left three months later and married someone else within a year and a half.
The real gut punch was that I had already custom-sized the ring. Trust me, we had talked endlessly about it before I decided to buy it. Because of the sizing, I couldn't return it. After a year and a half, I still have it. I often fantasize about taking a break with nine friends and tossing it into a volcano. 
Leah Kelley, Pexels
20. That’s A Lot Of Hot Air
My mom had her birthday and her wish was to experience a hot air balloon journey. Typically, these outings are shared with a group of folks you've never met before.
During the flight, one guy decided to propose to his girlfriend. Dropping to one knee, he revealed the engagement ring and asked her to marry him. What was her reaction? Well, her response broke me. "This is the third time you've proposed. Did you believe riding this balloon would change my answer?"
My mom mentioned the atmosphere was quite uncomfortable for the remaining part of the trip, so I can only imagine it must have made the whole experience less enjoyable. 
fizkes, Shutterstock
21. Get Me Outta Here
When we strolled down the beach, just like we usually do, it was crowded. An airplane flew overhead, trailing a banner that read, "Tiffany, will you marry me?" My girlfriend immediately exclaimed, "Yes" and hugged me tightly. To say I was taken aback would be an understatement—I stared at the sky, trying to figure out what was happening.
It took a moment, but she finally realized her mistake. The silence on our walk home felt painfully long, and I found myself wishing for some dramatic distraction—like a fiery boat explosion—tto break the dismal mood.
Talk about a crazy mix-up! It was tough, but surprisingly, she handled it quite well.Yeti studio, Shutterstock
22. So Unexpected
In the past, I held a job at a quick-service eatery. A familiar face, who came by often in the five years I served him, one day, requested to have a chat with me in the dining area. Given our acquaintance, I saw no harm in honoring his request.
Then, he complimented me on my looks and non-judgmental character in the cozy confines of one of the booths. A sinking feeling began to set in...something felt off. And right then, he popped the question: he asked me to marry him.
Next, he related a lengthy tale about how he perceived me as a reliable person. He's been in our country for quite a while, and he envisaged a long road to obtaining citizenship. While I was flattered, I politely informed him about my serious relationship with my boyfriend.
Undeterred, he suggested a deal, I could continue my relationship and in return for marrying him, he'd financially support me and shower me with gifts. I gently let him down again.
His spirits took a hit, and ever since, whenever he visited the restaurant, he'd continually inquire about my marital status. It started to vex me. So, I decided to wear a faux ring one day and told him that my boyfriend and I were happily married now. 
Gligatron, Shutterstock
23. Hide But Don’t Seek
I was at my boyfriend's cousin's place for Easter. He was about 24 years old back then. His plan was to hide a ring inside an Easter egg for his girlfriend and send her on an Easter egg hunt.
The whole morning, he worked on organizing the event, assigning folks to take photos, get the champagne ready, and so on. When his girlfriend arrived, he excitedly told her about the Easter egg hunt he planned. To his surprise, she was less than thrilled—she complained about being tired and dismissed the egg hunt as nonsense.
He eventually gave in and told her there was something truly special waiting for her in one egg which he believed would excite her. Her response was rather shocking as she said, "If it's a supposed engagement ring, the answer is no."
Watching that unfold was heart-wrenching. 
Prostock-studio, Shutterstock
24. Brutal Misunderstanding
So, a friend of mine presented his on-off girlfriend of 10 years with a ring for Christmas. I'm really not sure how their chat went when she unwrapped her gift. Nevertheless, she took to Facebook to announce that it was an engagement ring and that they would share the rest of their lives together.
That post, complete with the picture, scored a ton of likes. Without Facebook himself, I decided to call my buddy to offer my congrats, but he seemed confused about what exactly I was congratulating him for. Once he realized the Facebook post she made, it became clear he was peeved— he didn't intend the ring as a proposal!
He ended our call abruptly to clear things up with her. Unsurprisingly, the Facebook post featuring the ring evaporated not long after. 
theshots.co, Shutterstock
25. A Weekend To Forget
Once, when I worked at a jewelry shop in a small town, a young man, around 22-24 years old, walked in with his little brother. The elder was enthusiastic while his younger sibling seemed cautious, even making remarks trying to dissuade him.
He purchased a ring worth $1500. Before finalizing the sale, I made it clear there were no cash refunds, only store credit would be given for returns. Seemingly unfazed, he simply replied, "OK"!
Then came the following Monday. He returned to the store sporting a black eye, wanting to exchange the ring.
I couldn't help but feel sympathetic towards him. 
FOX, Pexels
26. No Regrets
I was putting money aside to buy an engagement ring. My plan was to propose to my girlfriend, but sadly, she cheated on me the day before I was set to purchase the ring. Instead, I bought a large bong. Looking back, I have no regrets. 
Andrea Piacquadio, Pexels
27. Unexpected Outcome
I caught her on a phone call expressing anxiety about my potential proposal and stating she wanted to break up. Directly after that chat, she ended our relationship. I had already bought an engagement ring.
Going back to the jewelry store to return it was a heart-wrenching experience, and I fell to pieces trying to explain my reason for the return. That was my rock bottom moment—yet, it was also the turning point.
That's because the girl working at the counter insisted we go for drinks that night. We ended up laughing about the entire situation, making it an unexpectedly great time.
Fast forward three days to today, and the jewelry store girl has dropped me a message. She's asked if I'd be interested in an unplanned New Year's trip with her. I've spent all day just looking at the message. 
Ruslan Grumble, Shutterstock
28. Young Love
When I was a young, naïve 21-year-old, I thought I was in love. We'd been a couple for three years. But it was a turbulent relationship. She used me to improve her self-esteem, and I was blind to the fact that a loving relationship shouldn't bring me to tears on a weekly basis.
One day, amid a heated argument in a Bank of America parking lot, I was convinced she was about to leave me. In a desperate plea, I shouted, "Just marry me! Let's tie the knot!" Surprisingly, she agreed and we made plans to get married the following month.
I was filled with joy, convincing myself that I had discovered my soulmate. I went ahead and splurged a hefty sum on an engagement ring, presenting it to her that very weekend.
We decided to share a bath. However, as I was giving her a shoulder massage, she bluntly confessed to a heartbreaking truth—she had been cheating on me with three different men that month. Without uttering a word, I got out of the tub, pulled up my jeans over my damp legs, and left her house.
I drove off and never spoke to her after that. That was six years back, and I'm still recovering from the emotional blow. 
fizkes, Shutterstock
29. Beyond Heartbroken
For close to two years, I was in a relationship with a wonderful girl who was dear to me—she was my best friend. We shared a bond so strong and always enjoyed each other's company.
Last winter, in December, I decided to switch to a more lucrative job to solidify our coming future. And with my first paycheck, I bought a diamond engagement ring. On the 12th of January this year, with heightened emotions and joyous anticipation, I asked her to marry me.
Her reaction was one of surprise, but she requested some time to mull it over. I respected her wish and gave her some breathing room, but the ultimate answer was a "No".
Since then, my world's been a bit shattered. I haven't found the courage to date anyone else for almost seven months now – she's still pretty much on my mind. Changing this seems to be more difficult than I imagined it would be. 
Pixel-Shot, Shutterstock
30. I Proposed To The Devil Itself
I was in a relationship with a wonderful girl for slightly more than five years. When we first started dating, she was healing from a toxic and harmful past relationship, which left her struggling with trust issues, damaged self-esteem, bouts of depression, and self-harming tendencies.
Despite these hurdles, I found myself falling deeply in love with her. I supported her throughout her healing process, easing her emotional pain. In fact, we went to bi-weekly therapy sessions, which I funded, and we shared a home for most of the relationship.
Fast-forward to our fifth anniversary, I was smitten with her, so I decided to propose. I presumed the feeling was mutual from her side, and to my delight, she said yes.
However, a curveball was thrown my way a few months later. After finishing work earlier than usual, I decided to surprise her with her favorite fish and chips for dinner. Unbeknownst to me, my world was about to be flipped upside down.
In a nutshell, I arrived home to find her in our bed with another guy. They were so engrossed that they didn't even notice me entering the apartment.
Within 48 hours of this shocking incident, she had moved out. Not only did she vacate our shared apartment, but she also took with her half of my belongings. This included my cash savings, my TV, and a lot of my kitchenware. She even decided to keep the engagement ring. The worst part was—she took my beloved dog.
I haven't had any contact with her since that day, which now was about three years ago. 
Helena Lopes, Pexels
31. Stop It Already
A student of mine from the fifth grade has asked for my hand in marriage thrice already. The first attempt involved a Cheerio. The second proposition came with a cookie. And the last one? A scrap of tape. Each time, I have firmly rejected the proposal. It's somewhat adorable, sure.
However, WOW, this kid can be tiresome. There I am, imparting the knowledge to calculate the least common multiple for sorting fractions, and he's proposing? Come on buddy, solve this problem. You're the only one in here who's struggling with it. I'm here to help you.
Please, pay attention and don't let your youthful, 10-year-old curiosity wander off into strange territories. 
Tima Miroshnichenko, Pexels
32. Boy, Was He Wrong
Back when I was in third grade, an unexpected event occurred. Some guy strolled into our classroom and popped the big question to our teacher. In response, she burst into tears and bolted out of the room. We later discovered that she declined his proposal.
It seemed like he thought the situation of being surrounded by her students might pressure her into accepting his proposal. 
Yeti studio, Shutterstock
33. Shocking Revelation
After a three-year romance and a shared home for a year, I decided it was time to pop the question using my great-grandmother's valued wedding ring. However, she declined my proposal.
This occurred on a Friday evening. A couple of days later, after she returned from visiting her parents, she confessed to me that she was attracted to women. All this happened two decades and two years ago.
From that point on, life took its own course. I've been happily wedded to the next woman I fell for, and she proudly wears my great-grandmother's ring. That's been our blissful state for the past 16 years.
As for my ex, she now shares her life with her partner, with whom she's been for nearly the same amount of time. As for me, I'm a father to a wonderful daughter, and they are parents to two amazing kids—a girl and a boy. I hold great affection for them; they truly are the best individuals you could ever meet. 
fizkes, Shutterstock
34. That’s Reel Life
My father popped the question to my mother after they'd been together for a few years. She didn't say yes, which led to them parting ways.
Following a few months of my dad nursing a broken heart, my grandfather sadly passed away. This caused my mom to seek comfort and she reached out to my dad. They ended up finding each other, dating for a few more years, and eventually agreed to tie the knot.
I have to tell you, the first time I saw High Fidelity was a total mind-blow. Basically, the storyline mirrors my parents' lives—although, unlike the character in the film, mixtapes aren't my dad's thing at all. 
Prostock-studio, Shutterstock
35. Persistence Doesn’t Pay Off
Once, while dining at a fancy restaurant with my girlfriend, we saw a gentleman at a nearby table getting ready to propose.
Caught off guard, I was astonished. I thought, how incredible it is to be witnessing such a monumental moment in a young man's life. But, things didn't go as planned. The woman rejected his proposal.
Ignoring her rejection, he kept on his knee, desperately seeking reasons. The woman, mortified by now, urged him to stand. Instead, he began to cry. People around him tried to lift his spirit with cheering words like, "You'll get her next time, buddy!" or "Don't worry about her, champ!"
The whole situation was uncomfortably awkward. 
Prostock-studio, Shutterstock
36. You Broke My Heart
I was in a relationship with my ex-girlfriend from the time I was 14 until I was 24, but we broke up six months ago.
When I turned 16, I was certain that she was the one I wanted to spend the rest of my life with. I worked part-time and saved for a few months to buy the best ring I could afford from Zales.
I chose Hook Mountain, a picturesque location near where I grew up, overlooking the Hudson River, to pop the question. I knew she loved me, so I wasn't anxious—but looking back, maybe I should've been.
My memory of that moment is hazy, I don't remember exactly what I said. But her reaction to my proposal was evident—she was terrified. She confessed her love for me but admitted she wasn't ready to settle down with me. I was disappointed, to say the least.
To lighten the mood, we left the mountain trail and grabbed some ice cream. I stayed mostly quiet after that. I returned the ring and kept the incident to myself, not even telling my closest friends or family.
Today, six months after our breakup, she still crosses my mind every day. My love for her runs deep and I suspect it always will. 
wk1003mike, Shutterstock
37. Not Good Enough
In their family, there was a charming Christmas tradition. Mom and Dad would tuck a pickle ornament away in the branches of the Christmas tree, and the children would all race to see who could spot it first.
The reward for the ground rules winner was an additional gift. I thought this would be a novel, personal way to propose, and approached my girlfriend's parents and siblings about my plan. They thought it was the best idea.
However, when they rigged the game so she could find the ring, her reaction was a total shock. She didn’t just decline the proposal but demanded that I leave. We haven’t spoken since. It seems like four years of dedication and love weren't enough! 
My Ocean Production, Shutterstock
38. Close Call
I was in a relationship with a girl for four years. Two years in, she expressed her desire for us to get married. Initially, I wasn't sure, but she helped me realize how important this step was to her. Personally, I didn't see marriage as an essential part of a successful relationship and thought it only complicated things with paperwork.
Yet, I decided to go for it. I bought a ring and kept it hidden for a few weeks while I planned the perfect proposal. However, I found out she was unfaithful because she thought I was taking too long to ask her. Heartbroken, I chucked the ring into a dumpster, wanting nothing more to do with it.
Ironically, she fell short of being married by just five days. She even discovered the date I intended to propose because I had taken the day off work to prepare everything. 
VGstockstudio, Shutterstock
39. That Hurts
I've been going out with this girl for some time. One day, we took a stroll and I suddenly knelt down. I gently held her hand, and I could see tears starting to form in her eyes. And then I popped the question: "Can you hold on a sec while I tie my shoe?"
Boy, she slapped me harder than anyone ever has before. 
Anna Tryhub, Shutterstock
40. Missing You
I've been in a relationship with my girlfriend for more than two years, but we've known each other for even longer. We'd often talk about tying the knot, although we mutually agreed that we'd wait until she wrapped up her grad studies.
She ended up moving to Penn State after finishing up at Purdue in the autumn of 2012. Holding on to the traditional beliefs of her family, I didn't move in with her, opting to stay put in Indiana instead.
We kept in touch daily and managed a few face-to-face meetings whenever she was in the tri-state area. A month-long plan was put in place for me to visit her at Penn State for a week. Prior to this trip, we maintained our daily chats and things seemed to be sailing smooth.
To ensure I had enough money for this special visit, I even put in extra hours at work for a straight month. I also bought a ring—despite our earlier decision to wait.
My intention? To show her that, despite the distance, my love for her couldn't be shaken. Post a twelve-hour drive, I finally reached her place. We enjoyed a pleasant day together before calling it a day.
Being an insomniac, I struggled to fall asleep. So, I asked if I could use her netbook to keep myself occupied until sleep beckoned. The Skype window was flashing once I logged in. My pulse quickened. It was a conversation she had with her ex-boyfriend—spans of chat history.
Turns out, just less than two weeks into her move to Penn State, he visited her and they'd been intimate. I woke her up, sparking a heated argument which lasted a few hours. I then made the long drive back home. During our altercation, I tossed my luggage into the yard through the sliding door.
Unbeknownst to me, the pocket holding the ring was open and I ended up losing it somewhere in her yard. I only realized this misfortune when I made it back to Indiana.
I also had to bid farewell to a lovable dog that I'd raised from a puppy to a one-year-old. Since my roommate developed an unexpected issue with dogs, I'd given her to my now ex.
Fast forward a year, and I still miss my furry friend something terrible. 
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41. Gone But Not Forgotten
When we got back from our Christmas vacation, I brought up the topic of marriage with her. Her response was a clear no. Not just a no, but a proclamation that she had never considered marriage with me, and she never would. This was swiftly followed by a half-hour monologue where she expressed her yearning for her singlehood.
I won't lie, it hurt me deeply. I did make an attempt to salvage our relationship, but looking back, I guess my efforts dwindled after her blunt rejection. Fast forward eight months and she moved out.
Only three months later, she pleaded with me to accept her back and even expressed her desire to marry me and buy a house together. The wound, however, was too raw to trust her words.
I've found some solace in therapy, to be honest. Regardless, that was the day a five-year relationship crumbled. As time flies, I miss the relationship we once shared, but I'm unsure if I still miss her the same way. 
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42. My Soulmate
My buddy's parents first crossed paths at a beachside pub. Her dad fell head over heels for her mom, though his feelings weren't reciprocated at first. After a spontaneous one-night fling, she decided to give him the silent treatment. That is until she discovered she was carrying a child.
Upon hearing the news, he was overjoyed. She was resolute about having the baby. He repeatedly tried to build a relationship with her, but was rebuffed every time. His numerous proposals were met with dismissive glances and resounding "No!" from her end.
Fast forward to nine months later, when she began to experience labor pains. She invited him to accompany her in the childbirth room. Just her and this man who was persistently asking her for her hand in marriage. A few hours into the arduous process, the medical staff observed an issue—the baby's heartbeat was abruptly slowing.
As the mother was swarmed by panic, the father remained an anchor of calm. He stood by her side and relayed information from the medical team. However, there was little anyone could alter the course of the events. They were devastated when the baby was stillborn.
After confronting such a profound experience, my friend's mom acknowledged that she had discovered her life partner. From that point forward, they committed to be together and are happily married even today. 
Prostock-studio, Shutterstock
43. Worst Timing Ever
My best pal had been seeing this guy for nearly two years. I noticed that their relationship was losing its spark. One day, over lunch, she confessed to me she'd decided to call it quits with him. Her concern for him was just so clear. As we continued the lunch, she was figuring out their break-up plan and asking what I thought.
Just as I was racking my brain to come up with some advice, the guy made his entrance, a bit rattled. Maybe she'd told him where she was going, and he decided to show up. Bravely, he walked up to our table, totally ignoring me. Kneeling down, he pulled out an engagement ring.
He was trembling and the timing couldn't have been worse. My jaw dropped in disbelief. The excitement from the onlookers made them crowd around our table, cheering. Then, the guy popped the question to my friend. But all she did was walk out, get into her car, and drive off.
Second-hand embarrassment almost knocked me out. What stuck out in my memory were the gasps and chuckled comments of those nearby. He just sat down where she had been, looking utterly heartbroken. I was lost for words. Feeling a bit sorry for him, I quickly covered the bill and tried to comfort him with a pat on the back. 
Prostock-studio, Shutterstock
44. What A Load Of Garbage
I'm a guy and I had been dating another guy for quite a while. I had a hunch that he might be stepping out with his former flame for some time.
During a few months' trip to Italy, my best friend decided to send me pics of my partner and his ex deeply engrossed in a kiss at some pub. Surprisingly, I remained cool and composed, because I had my payback plan ready.
The very next day, I went ahead and purchased a ring before catching a flight back to the States. Upon landing, I surprised him with a marriage proposal right there at the airport terminal. His refusal came attached with an infuriating reason—that it was premature.
To that I showed him the incriminating photo of him and his ex and shot back, "Are you sure it's not because you're behaving like total trash?" I promptly took back the ring, and a fortnight later, he moved out. 
Dean Drobot, Shutterstock
45. Perfect Setting For A Letdown
I was in a on-and-off relationship with a girl for a span of 12 years. As of recently, we'd been committed to each other for a straight six years. We went on a trip together to the Philippines, where we found ourselves swimming in a breathtaking lagoon. It was then I thought was the perfect moment to pop the question. I started off with, "Hey, baby…" She must've sensed something because she quickly spun around and said, "Don't do it".
Her words swiftly deflated my excitement. However, a couple of months down the line in Australia, she actually said yes. 
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46. What A Waste
My former sweetheart popped the question on February 29th, 1992. I declined– I was too young to understand. We separated but eventually reunited. Now, we've been blissfully wedded for 19 years. Unfortunately, my initial denial resulted in five long, missed years!
47. Out Of The Blue
Several years back, I had a job on a cruise ship, serving in the main dining room. My workspace was always the same spot, and I was coupled with the same five-person team each evening. Among them was an adorable Filipina with whom I often struck up playful flirts during our shifts—we hit it off splendidly.
About a month into this, thoughts of possibly moving beyond mere banter with her started forming in my mind. Funnily enough, she seemed to be on the same page! One evening, as we were tidying up after work, she popped the question—"How about we get married?" I chuckled and replied, playfully, "Sure, why not?" under the impression that we were merely joking around.
Turned out, she was dead serious. She even offered to pay me $3000, which, nonetheless, I declined.
In the period that followed, things suddenly got super awkward between us. She hardly said a word to me for the remaining duration of our contract. I would like to believe that she did this more out of being heartbroken, and less because I wouldn't assist her in acquiring citizenship. Regardless, I was left feeling awful but at the same time astounded that I had actually been proposed to!
48. Message Received
After about a month of going out, he surprised me by popping the question with this MASSIVE diamond ring. And there was this long mushy proposal of something like "You just know when it's right. Will you marry me?"
Considering I was barely getting to know him, I rejected his proposal right away, adding "Sorry—are you alright?"
He didn't say a word to me for the rest of the evening. After he dropped me off, I spilled the beans to my roommate. While I'm recounting the event, he texts me—believe it, a TEXT. It read, "You've shattered my heart. Never want to cross paths again. Farewell. I love you".
The kicker? We were both just 22 at that point.
49. Say Cheeze!
I took a plane from Texas to Wisconsin to unexpectedly show up at her college graduation. I kept it under wraps, insisting I wouldn't be able to attend just to add to the surprise.
I coordinated with a friend to have her at the right place at the right time, showing up just as she turned the corner. In hindsight, hiring a photographer to capture everything was a blunder that just made things worse.
When I got down on one knee, she said yes. We celebrated that night over dinner when she confessed her real feelings. She admitted that she had only agreed to engage me because of the crowd that was present.
Here's some advice: think twice before popping the question in public. That was the most painful part of my experience. Despite this, I hung on for another year and a half before we called it quits.
50. Duped
When I popped the question, she shockingly revealed that she couldn't tie the knot with me because she was already promised to someone else. During the three years we were an item, it turns out she was seeing someone else all along.
Nicoleta Ionescu, Shutterstock
Sources: Reddit,
