I had the ring for quite awhile before I proposed. It was a family heirloom – my Great Aunt’s wedding ring. Fortunately, A) it fit my wife-to-be perfectly, and B) she said “yes”. 
I find that so sweet and romantic!
As for me: The first time, he proposed in the middle of the night, in the heat of an argument, and then dashed out and bought the ring the next morning. Nice ring, just what I would have chosen, and I married him (and divorced him sometime later).
The second time, he bought the ring first and proposed on Christmas Eve. But he used my money to buy the ring, and that money had been set aside for rent. I didn’t marry him.
The last time, he proposed via IM. By the time we got around to buying the rings, I was shacked up and knocked up, so I picked out my own. I’m still married to him.
He proposed without a ring. I didn’t want one. If I had, I would imagine he’d still have proposed without it, and then bought it together.
(Don’t see the point of the woman ‘marking’ herself as unavailable when the man doesn’t do the same.)
My brother has been engaged to two girls, and he proposed with a ring both times. The first he bought himself, but sadly that relationship failed. When he met his new girlfriend, her parents sized him up and then her mother took him aside and told him he had her blessing if he ever wanted to marry her daughter, and she gave him an engagement ring that she said she had bought for her daughter years before - when she was buying one for her older daughter! A mother buying an engagement ring for her daughter is a custom I hadn’t heard of before but I guess it worked out nicely for my brother. They married earlier this year, so I hope my brother is done proposing to people.
I never did get an engagement ring. I’m not really into jewelry and we bought a house immediately after our engagement so it just never happened.
Mr. Rilch proposed without a ring, but it was still highly romantic. It was the day before his cousin’s wedding, and both bride’s and groom’s extended families were lodged at a country inn in Massachusetts, in October, with the leaves in full color-saturation. Mr. Rilch suggested we take a paddle boat out onto the lake while everyone else was in the bar. Which we didn’t realize would take us right past and about a foot from the huge picture window, behind which twenty-five or so people were all watching us and laughing. Because Mr. Rilch is large and I am small, see? And his uncle J., the father of the bride, was holding his hands out level, one about ten inches higher than the other, to demonstrate how unbalanced the boat supposedly was (it wasn’t!) and Mr. Rilch waved and muttered through a clenched smile.
Anyway, we got out to the middle of the lake, and he asked me. And as I said afterwards, I had to say yes or he would have pushed me overboard. No, he really wouldn’t have, but since I’m a weak swimmer even when I’m dressed for it, and in this case, I was wearing jeans, a sweater over a turtleneck, and heavy shoes, I was rather nervous just being in that boat, and when I realized what he was getting at, I could only say “Y-y-y-yeah…okay! Yeah…okay! I mean, yeah…okay! Uh…I love you!” He wanted to kiss, but I held off on that for the above-stated reasons. (I think there was a soap opera where the woman did react joyously to such a proposal, and fell overboard and almost drowned and did lose the ring.)
So we paddled around the lake a bit more, then went back inside and took Mr. Rilch’s parents (who were still married) aside to tell them the news discreetly. MIL was overjoyed; FIL immediately asked where the ring was. Mr. Rilch gave him the answer oft-repeated in this thread, to which I said, “Oh, I’d have loved any ring you chose!”
And in fact, we still don’t have wedding rings. I do have his grandmother’s engagement ring, but it’s too large. Doesn’t matter, though. One of these days.
Maureen, I had totally forgotten about that! You are one lucky gal!
My husband had the ring when he proposed. He was a jeweller and knows me inside out so his choice was perfect. The ring really suits me and is an unusual design. I choose the wedding ring which he had to alter so that the engagement ring would sit well with it - I am complimented on both all the time and people often think they’re a set.
I had the ring all ready. I found a ring that was just the right size and had multiple small diamonds in a pattern I klnew Pepper Mill woukld love (PM doesn’t like gaudy), so I had it in hand when I took her to the Fancy Restaurant. Pepper knew exactly what was going on – we didn’t usually go to Fancy Expensiv Restaurants – but she cried when I gave her the ring. The musician making the rounds of the tables tried to subtly make his way over to have a look, as did a couple returning to their seats, making a slght detour. They were probably disappointed – the ring isn’t all that impressive.
I didn’t actually ask Pepper, in words, until later, though. I’d done all this without saying anything, and realized when we were on our wauy back to the car that I hadn’t ctually asked her to marry me, and she hadn’t actually accepted. So I asked her to marry me in an underground parking garage. She accepted. I think she liked the ring.
First proposal I received:
I found out my bf was the roaming kind and told him that I wasn’t interested in seeing him again, and to please wait a bit and I’d give him back the books I had on loan from his mom. He said “but… but… but… uhhhh… will you marry me?”
No.
Second:
I was having to leave the US because my employers didn’t see the need to “keep me legal”; they wanted me to stay, but illegally. Bf asked me to marry him “so I wouldn’t have to leave and throw away my career”, in a restaurant, with people listening, down on one knee, no ring. No. Sorry, only because you’ve turned this into a circus doesn’t mean I’ll jump through hoops; going back to the home country is not the same as throwing away my career, I’m from Spain, not the Kingdom of St Potato Martyr. If he’d coached the proposal in different terms I might have said yes, but hell - it just wasn’t right.
My brother met this girl from a nearby town during an Easter retreat hosted by our parish. He pursued her for several weeks; her gf’s considered him as his bf but she insisted he was “just a friend” - u-hu. On her Bday (July 19) he gave her a silver band as a gift and asked her to be his girlfriend; she accepted. She told the other people in the party; he kept his hands in his pockets while people congratulated them. When he brought his hands out, he was wearing a silver band identical to hers.
I don’t know the details on what went on several days before he came home one day saying “we’re getting married in november”. Their wedding bands are plain gold bands, identical to the silver ones except for the material. They took off the silver ones and replaced them at the wedding.
Only Mostly Dead had the ring beforehand. We had talked of marriage many times and when he got his real job after graduation, we knew it wasn’t far away, so I went and had my finger measured. He had specific instructions, and still managed to make it a complete surprise. Not on one knee, but I wouldn’t trade it for any proposal in the world.
I, and all of my married/engaged friends, were all proposed to Hollywood-styles, ring included.
It was much more romantic that way, and anyhow, it showed he was serious about it, and meant so much that he had been planning it for so long.
Sweet story. I like to hear about Deb – she’s so prominant here (because of being in your username) and yet mysterious.
I’ve known lots of people who were proposed to Hollywood-style. My business partner (who has been married 3 years) is one off the top of my head. Also my parents (who just celebrated their 49th a couple of days ago).
My first husband and I did it the other way – he proposed sans ring and we went out a couple of days later and chose a ring together.
My second husband (to whom I’ve been married 20 years), didn’t propose at all – we just decided to get married, without either of us proposing formally. I didn’t have an engagment ring – we knew I was going to be staying home with the kids (once they came), so we opted to use the ‘engagment ring money’ to pay off bills so we could start out on one income without debt.
For our 10th anniversary, though, Kevin designed a diamond ring for me (marquise diamond in the center, with our birthstones on one side, and the kid’s birthstones on the other) and had it made. We call it my engagement ring, for lack of anything else to call it.
I did the whole down-on-one-knee thing for Lady Chance one snowy Spring break day. Ring and everything right around the corner from her parents place.
I borrowed money from my mom for the ring. Ruby set at a hippy geology/jewelry place in Annandale that mom dug (she loves her rocks, Mom does).
Endnotes:
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Mom forgave the debt as my graduation present.
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Lady Chance no longer wears it…not since we got married. She turned it into a tiara for one of her Barbie dolls. It’s on a bookshelf at the moment.
I had the ring already. We had gone ring shopping before, to check out different styles, I wasn’t going to get an expensive ring that was the wrong style. It also vetted the idea of getting married, so I was pretty confident that she was going to say yes, and she was pretty sure I was going to ask.
He had the ring. He also basically knew what I wanted, because we’d discussed it in the past (I wanted sapphires as part of my ring because we both have September birthdays). The setting and any other stones was left up to him. I think he got my ring size from my mom. I picked out his ring without him seeing it too, though I also knew basically what he wanted (no stones!). We’re both happy with each other’s choices, and each other.
After dating for three years in college and then both moving to the same city, my engagement was pretty much a foregone conclusion. In fact, her sisters had picked out bridesmaids’ dresses and her mom and reserved the church before we were “officially” engaged.
As for the ring itself, we went ring shopping together so she could show me the style of band and stones she liked. I picked out the ring myself, though it was essentially what she had already picked, just with much bigger stones (I wanted there to be some surprise involved ). I gave it to her when I “officially” proposed.
He proposed over an episode of the Simpsons (the one where Homer proposes to Marge), but sans ring because we had a family heirloom diamond that he’d been left by his grandmother. We ended up going together to have it re-set in a setting that I chose, which was fine with me (he and I have wildly varying tastes on what an engagement ring is - he would’ve had it set as a plain solitaire in yellow gold, whereas I preferred something with sapphire sidestones in platinum or white gold - had we not had the heirloom diamond, I actually just wanted an engagement ring with a sapphire center stone.)
E.
I bought the ring ahead of time. I felt like I knew what she’d like.
Then I planned a surprise party with all of our closest friends. That night, I lured her into Central Park to go “ice skating” and then proposed under what is now Our Tree. Then I told her that her best friend knew I was going to propose and was making us dinner (he’s an amazing cook). When we got there 50 people were waiting and there was a feast of unbelievable food. An incredible, special night for both of us. Topped only by the wedding.
She loves the ring.
I had the ring made–I’d playfully measured his finger with foil from a gum wrapper.
It was our anniversary and I’d had an elaborate plan of proposing to him on a mountaintop where one could see what seemed like the whole Delta, but we’d awakened to our dog having a swollen face from an abcessed tooth and after the surgery none of us were up for hiking.
So I brought him a pint of Ben & Jerry’s Chunky Monkey with a ring sticking out of it and told him I loved him, wanted to spend the rest of my life with him and he would make me a very happy woman if he would consent to be my husband. Or something like that.
So, not as romantic as I’d hoped but really more “lifestyle appropriate” for us. 
I’m also one of those who proposed hollywood style, already having the ring. It just strikes me as so much more romantic and stylish to do it that way, I wouldn’t have considered doing it any other way. Of course, I’m pretty traditional about those sorts of things…had my wife’s dad been alive, I’d have asked permission and all that stuff.
The only thing I did wrong was that I used one of her right-handed rings to get the size. It ended up being too small (I think) for her left hand, and we had to get it resized. Drat!
Susan, that’s a rather recent development, isn’t it? Congrats!
I had the ring and went down on my knee new year’s eve 2003. She said yes.