You really have to put yourself out there when you propose. To ensure you won't get a "no" from your significant other, check out these stories from people who did all the wrong things in the big moment.
Who’s Getting Married Anyway?
I dated a girl for almost 3 years. We were both 24 and had been done with college for a couple of years. Everything was going great and it seemed like it was the right time to start planning for our future. I went on my own to talk to her dad one day when I was considering a proposal, and he shut me down right away. He then shared that my girlfriend and his wife and him had been wondering if I was leaning this way and my visit had confirmed it. They had jointly decided that they weren’t comfortable with me getting married to their daughter and my girlfriend was in agreement. When I pressed for details, it seemed that they did not like the fact that I was a schoolteacher and were worried about my ability to earn a good living. Otherwise, they said I was a good guy, just a little bit short in the ambition department. They were looking for their daughter to marry someone who had greatness on the horizon. We broke up the next day. (Source)
Selfishness Is Not an Attractive Quality in a Fiancee
I knew a girl like this. She dated the guy for 5-6 years and they were talking about marriage and he told her to pick out the ring. She went and picked a ring that would cost 4 months worth of the guy’s salary, and I’m talking 4 months of him literally not spending a penny on anything other than the ring. He spent 2 months trying to talk to her about getting a ring he would actually be able to reasonably afford and she would flip out every single time he brought it up. They broke up the following month and she’s been single ever since (6+ years) and last I heard he’s been married for the last 2 years and is expecting his first kid in the next couple of months. (Source)
No Proposal But a Happy Ending
That is how my boyfriend did it.
We had been together for 2 years, and while we are close, we are also semi-distant. We had both gone through horribly painful heart shredding relationships (it nearly destroyed him… both involved our former partner cheating on us), so we had some seriously high walls and rarely let the other in. We were friends prior to dating so we knew about each other’s walls, so it never was an issue for us.
We always got a long really well, but never lived together and never had sleep overs. We do spend that vast majority of our time awake together. Then I got pregnant (def not what either of us wanted/planned, and we only learned a few weeks ago, and I’m just starting my 6th month… eek!), but it’s all been so surreal. Its like the walls came down and we’re totally new people, awesomely happy and excited people! We’re in our mid-30’s and both of us make good money, and both our families are stoked about the news, even though they had no idea either of us had even been dating. lol.
We’re buying a house together, and he asked if I was interested in getting married to him down the road. I told him yes and smiled pretty hard. He said not right now, as we need to get the house and baby figured out first, which I completely agree with. We also mentioned we need to think about (later) on how to do a non-$20,000 wedding, as he (nor I) want to waste money on a crazy frilly foo foo wedding (it’s just not us). So we’re totally on the same page, and I now get to play the waiting game. (Source)
Someday Your Prince Will Come (Not)
I had a football coach who also taught at our rival school. My junior year he decided to coach at his own school and that was last I heard of him until my senior year. Apparently he proposed to his girlfriend in front of the castle at Disneyland and she said no and then left. Not wanting to waste his money, he decided to stay in Disneyland until closing…by himself…probably depressed. (Source)
This One Shouldn’t Have Worked
I got my then girlfriend pregnant. One time we were helping my mom clean her basement, she asked us, are you guys going to get married? I turned to my girlfriend, and said, well do you want to? I’m up for it. She said yes. Looking back I regret it being so informal, but no ring, no plan, just a spur of the moment conversation. I was 19 at the time. I’m now happily married to her 15 years later. With a 14-year-old and 7-year-old. (Source)
A Minimalist Rejection That Gets to the Heart of Things
“You’re drunk. Go back to bed.” (Source)
Maybe a Proposal Is Worth Some Thought
True story: A friend of mine had never had a girlfriend before, his only true love was booze. Around 30 years old he spent most of his waking hours at a local bar, where he befriended a smoking hot, fake boobed, crazier than sh_t, ex-stripper that was now a waitress there. After her shift, she’d join him and they would get sh_tfaced together. Their booze filled romance blossomed over time, to the point where she would go back to his place after close so they could drink more. Naturally, this led to sexual liaisons. Before you knew it, my buddy had a real-life girlfriend. They were disgustingly drunk and affectionate with each other constantly, but my buddy was over the moon with happiness, so we let it be. After a couple months of this, buddy and girlfriend are having themselves a great Sunday watching sports at the bar. Around 10:00 p.m. or so, drunk buddy hops off his bar stool, gets down on a knee…and without a ring, proposes. The bar is cheering! She says “Yes!” Buddy orders champagne for everyone!!! Slaps on the back, congratulations passed around, shots bought for the new couple. A couple hours later, even more drunk, he gets down on a knee and proposes again!!! He’s then reminded he already had done it. So, which I imagine was only to save face, slurs “I mean tonight!!! Let’s go to Vegas!!” So they hop in a cab, and 80 dollars later are at the airport. No flights available until the next morning. So they decide to sleep at the airport. Upon waking up, they decide they had better wait…80 dollar fare back to the bar, then they each go to their own home. So no marriage. In the end, very long story short; A a few months later she suspected him of cheating (he wasn’t), slapped him around a bit, and they broke up. (Source)
He Was Definitely Too Good for Her
The ring wasn’t big enough. I had saved for months and we had talked about it. I had set up a date night and went to one of the more expensive restaurants. Suit and tie kinda place. When I got down on one knee I could see her eyes light up but when I said my piece and opened the box her whole demeanor changed then she asked if we could ‘do this somewhere else.’ Most embarrassing moment of my life. We broke up shortly after. (Source)
Who Says the Guy Has to Propose?
I’m not suspicious…we’d not been together too long, and I now realize she just jumps into things crazy fast. Yeah, she proposed to me. Given how quickly she moved on, I think she’s more interested in the idea of being married than any particular person. (Source)
When Your Friend Isn’t Really a Friend
My buddy dated a girl for a few years (with several break ups sprinkled throughout), then ultimately broke up with her. Like 6 months later she was married to one of her guy friends who was always hitting on her and inviting her to concerts when she was still dating my friend. We were all glad he dodged that bullet. (Source)
Taking No the First Time
I’ve seen a lot of them go well, and more than a few go bad. Guys, if she said no the first three times, don’t think that taking her on a nice trip is going to change her mind. You’ll just end up with the same answer, a big travel and hotel bill, and a very uncomfortable trip home. Second biggest mistake, wayyyyy too early. If she has a look of total shock on her face when the ring comes out, you probably should have had a talk first. Making sure it’s a surprise is not always as important as making sure it’s a good surprise. Two months in is likely gonna be the former. The worst I ever saw though was the guy who asked, I had the ring on a dessert plate, and she said, “I’ve told you half a dozen times I have no intention of marrying you.” He got angry, snatched the ring and stormed out. She ate the dessert. He eventually came back and apologized, but I almost broke my cringing organ. (Source)
“Bermuda, Bahama, Come On, Pretty Mama”
I was planning a vacation cruise to the Bahamas. Went to surprise her with the tickets and caught her cheating with another man. I was going to propose on the cruise. Got my money back, we’ll most of it back and now here I sit alone. (Source)
Whatever You Do, Don’t Drop the Ring
One night my boyfriend drunkenly confessed he wanted to get married. I was shocked and told him I never wanted to get married again but was happy with him and wasn’t going anywhere.
2 years later, he proposes out of the blue while we’re wading around in a waterfall in Hawaii – and promptly dropped the ring in the water! Luckily I was able to fish it out, then I put it on and said, “thanks!” He just stared at me like, “well…?” I laughed and said yes and we got married 4 months later. Somehow the whole thing was so perfectly ridiculous that it made me realize that we were going to be together forever anyway, we might as well celebrate it! (Source)
If Your Would-Be Fiancee Starts Crying, Take It Seriously
Christmas day ’13 we where having christmas with my folks. Presents are basically complete, but I tell her there is one more hiding in the tree. I go to grab it and pull out a tiny box with a ring and propose to her. She looks at me with a slight pain in her eyes then starts crying and runs out of the room. I found out later she had cheated on me the night before, while I was finishing up a shift at work. (Source)