Yesterday, my husband, three of our kids, and their significant others got up at 4am, piled into two rental cars, and drove 90 minutes to the top of Haleakala (on Maui), to watch the sunrise and–the real reason we were there–to see my daughter’s lovely boyfriend propose to her. It was deeply romantic and very special.

My husband never really proposed to me. We just sort of agreed to get married and that was that. But I have had friends with fabulous and/or very funny proposals and I do love those stories. 

Perhaps my favorite is that of the older brother of an old friend. He and his girlfriend lived on the west coast of Florida. One afternoon, when his family was visiting, they went out on his boat. There, he got down on one knee and proposed with a ring with a very large diamond. She said “Yes!” and as he was sliding the ring on her hand, he stopped, shook his head, and said, “This ring isn’t nice enough for you.” He then tossed it overboard. 

A moment later, he pulled the real ring out of his pocket–the other was a cheapie from the mall. Now that takes chutzpah!

I also love the proposal of one of my husband’s family members. They were in bed, having just, ah, enjoyed themselves, and he said, wanna get married? She said yes, they got up, put on their clothes and went down to the courthouse. They’re still married decades later. 

Do you know any great proposal stories? I’d love to hear them! (I’m trying to think of any stellar ones in romance novels, but, honestly, I’ve been up for fourteen hours and my brain isn’t what it might be! If you can think of one from a novel, I’d love to hear that too!

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  1. We were living together, knew we were going to get married but hadn’t gotten engaged or set a date. We had just adopted two dogs from the pound and they needed all their shots, plus to be wormed, etc., so we dropped the dogs off at the vets and decided to walk around the local mall. We passed a jewelry store and saw a three-ring set (his & hers wedding rings plus an engagement ring) that we immediately liked. In we went and ten minutes later, an engagement ring was on my finger. After we picked up the dogs and got back to the car, my husband turned to me and said, “I don’t want you to think I’m taking anything for granted, so will you marry me?” We still laugh about us deciding to get married while the dogs were getting wormed. We’ve been together 38 years and are about to celebrate our 36th anniversary in a couple of months.

  2. Our engagement story is a bit unconventional. I’d been married before and since my divorce I seemed to find men who were fun, but only wanted casual. When I met my husband, my dad was in the end stages of terminal cancer and I was already grieving and in no mood to invest in someone emotionally and then be told they only want to be friends. So three weeks after we started dating (we’d spent most of our free time together) I decided to cut to the chase and asked him if he could see our relationship going anywhere. He answer was, “Do you want to get married?” My answer was yes. His reponse was, “Ok, then we’ll go pick out a ring. Where do you want to get dinner?” 🙂

    So that’s how I got engaged three weeks after we started dating and only two months from when we first been introduced. We married 5 months later and will celebrate 41 years in January. Best decision I ever made. When I read about quick attachments in romance novels I can give a lot of grace because I know it happens.

  3. Mr. Caz and I had been together for about 8 years and weren’t too bothered about getting married tbh. (I was divorced, so I’d already done it once!) But then we decided that yes, we did want kids after all and that being married would probably make the legalities easier. That was as far as we got at that stage – until a few months later when we discovered our eldest was on the way (oops!), and I wanted either to get married asap or wait until after she was born. As this was early January, we had a February wedding – took us about 6 weeks to organise it. I don’t think there was ever an actual proposal!

    This year was our 25th anniversary and 33 years together.

  4. This cute, smart, funny guy and I had been together for only a short time when he had to leave for an overseas assignment. He called me from the airport and asked me to marry him. I was stunned, and when I didn’t answer right away, he said, “You have to tell me. They’re calling my flight!” I said yes, and then the horrible man asked me to call his mother and let her know we were engaged. That was 39 years ago, and my kids continue to shake their heads at how reckless we were!

      1. My husband and I went out first on Memorial Day weekend, told our families we were engaged on July 4th weekend, and got married Labor Day weekend. That was 55 years ago.

        Yup, when you know, you know.

  5. My now-husband had a cold when he proposed. I told him I’d wait 48 hours before I told anyone, just in case it had been the Benadryl talking.

    Two nights later I was at a party, and a friend of mine came up to me and said, “What’s new with you?” I looked at the clock and said, “Well… ”

    Not only was that friend the DJ at our wedding, I was the first one he called when he got engaged to another dear friend of mine, more than a decade later.

  6. Not me but a friend. They were both in graduate school, and he said, “We should get married.Then we’d qualify for married student housing.” And yes, the marriage lasted happily so long as they both did live.

    1. I’ve seen couples get married for all sorts of deliberative reasons.

      One woman I know said to her boyfriend–they were both 28–“I want a baby by 30 so if you’re not going to marry me within the year, I’m out.” They were married for almost 25 years and the three kids they have are the light of the guy’s life.

      Another couple wed for health insurance–they are still married several decades later.

      I think it’s not the reason, it’s how you behave once you’ve made that commitment.

  7. Four months after they met, my parents heard about a club that was supposed to be very good, so they drove quite some distance to get there, only to discover that it was actually a gay bar. They decided to stay anyway, since they’d driven so far, and everyone was very welcoming. After they’d been there for a while, it occurred to my father that it would be great fun to tell his children that he had proposed to their mother in a gay bar, so he did, and she accepted. They eloped to Las Vegas shortly thereafter, with so little preparation that they didn’t have an engagement ring, a dress, or any plans for cohabitation. She went home to her apartment, he to his.

    Today is their fiftieth wedding anniversary.

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