Let's start with the most important factor in a proposal. If you don't know 100%, that the answer is "yes," then don't propose. I realize that this isn't the most romantic advice, but I have news for you. We're talking about marriage, a lifelong commitment that requires a lot of work and sacrifice. Maintaining a successful marriage isn't easy, and if you don't have the right partner by your side, you're already starting with a huge handicap. Part of having the right partner is the both of you being on the same page, and that includes the both of you having the same opinion on marriage. If only one of you is going to be committed to your marriage, then that's a problem.
This means that you two need to have several long, serious talks about where you see your relationship going. A decision to get married shouldn't be made in a romantic haze, in which you are so caught up in the moment that you haven't considered how the two of you plan to make a life together. Nor should it be used as an attempt to revitalize a struggling relationship, because that's only going to set you up for a huge fall.
If the relationship between the two of you isn't working, then getting married is the worst decision you can ever make. You can convince yourselves that the future is shiny and bright, mainly by focusing on the wedding and nothing else. Of course, you'll be ignoring the growing number of incompatibilities developing between the two of you. Eventually you're going to be confronted by the naked, stark reality that the two of you are stuck together and now have to deal with the mountain of issues you've ignored. That is not a recipe for success, and you'll save yourselves a lifetime of pain by just breaking up rather than forcing a marriage.
You're going to have to ask the tough questions. Where do you see this relationship going? Do you see me as someone you could spend your life with? What are your long-term goals, and do you see us as part of those goals? Ask about your future together. Talk about your future togather. Start planning a future together. While at first this conversation can be tough, it will reveal whether the two of you should start thinking about the Next Step.
Bring up marriage. You're allowed to talk about marriage even though you two are still dating. Granted, it's not the best conversation starter for a first date, but if you've been together long enough to refer to yourselves as "we," then it's time to talk. If you want to get married, make sure your other half shares that goal. You two can even talk about the possibility of the two of you getting married. Keep talking about it, keep sussing it out, keep having those serious conversations until you are both certain that marriage is a welcome possibility. (If you need to, take a road trip.)
Now that you know that the proposal will be greeted with success, there leaves one more question. How will you propose? There are two schools of though for proposals: a private, romantic affair or a public spectacle. Let's start with the public proposal.
Once again, let me save you some future grief. If you plan to make a public proposal, you need to make sure that's what she wants. (Now, I am making an assumption that this is a heterosexual relationship and that you plan to follow traditional norms with the man proposing to the woman. So, to make pronoun use easier, that's how I will refer to all the actors involved. However, these same principles will apply no matter who is proposing and whether it is a same or opposite sex couple.)
There's a simple reason you want to know whether she wants a public or private proposal. She might not like it if you spring this on her in public, she may not like anyone else involved in this very personal moment, and she may not like feeling backed in a corner and pressured to say "yes." It's possible she'll just succumb to the public pressure and then absolutely let you have it when you're alone. You might create a deep resentment that will take a long time for her to get over. She also might break up with you because she feels so violated and publicly humiliated. Again, just because you know she'll say yes doesn't mean that you should surprise her like this if you don't know how she feels about sharing this moment with the world (and in this day and age, the internet).
That's if she says "yes." She might reject your proposal, and the results are often painfully hilarious (to the rest of us). Suddenly your relationship will have some pretty big cracks, and those can take a while to get over. While a proposal rejection can become a funny story if you two do get married, it can also spell the beginning of the end of the relationship, and if this moment happened in front of everyone, it's that much worse.
As I said before, marriage is more than the proposal and wedding, it's building a life together, and a huge part of that involves communication. The proposal is no different. If you want to set the right tone for the proposal, you need to communicate. It's perfectly fine to just ask her if she'd want a public proposal. If she loves the idea, great. If she says she doesn't, take her on her word. Don't think that she'll get over it if you do the proposing. (That's almost as dangerous as thinking she'll get over not wanting children once she's married to you, but that's another column.)
Instead, this is a time when you prove your ability to listen and follow through. When she tells you what she wants, by all means give it to her. If she wants something private and intimate, then that's what you should arrange. This can be a great memory if you just follow some common sense.
The proposal is a test, and you need to pass it. How can she trust you if you don't honor her wishes? How can she be on the same page as you if you refuse to even show her the book? That's why you need to know the answer and how she wants it done.
This doesn't mean that there can't be elements of spontaneity in the proposal. Even though both of you know it's coming, she doesn't need to know the exact date and time. If she's all right with a public spectacle, she can still be surprised when it happens.
That's how it happened when I proposed. My wife and I knew we would be married. We'd talked about our future together, gone ring shopping, and I knew what she wanted, which was a very private proposal. That doesn't mean she wasn't insanely shocked when it happened, and let me assure you, I nailed it.
Now that we've gotten the science taken care of, let's talk about the art. Here's my formula for success for executing a proper proposal.
First, have a plan. Know where and when you will propose, because that's going to be a permanent memory between the two of you. Pick a location that's meaningful to the both of you, or somewhere so incredibly fun and wonderful that it's going to be a great tale.
Second, have something good to say. It doesn't have to be a Shakespearean soliloquy, but at least have something meaningful and romantic prepared. This is going to be a defining moment between the two of you, so try to have something more than "Wanna be my old lady?"
Third, don't take any chances. The more intricate and complicated you try to make this proposal, the more you risk it going wrong. If you put the ring in a glass or a cake, you risk it being swallowed. Trust me, very few women find getting their stomach pumped romantic. My advice is to keep it simple and idiot proof.
Finally, men, get down on one knee. Trust me, that matters. It's more than just tradition, though that is part of it. It's a gesture that says you will put the relationship, and her, above yourself. It shows that you will be a servant, not demand service. Plus, it's incredibly romantic, and when you tell the story of the proposal, you automatically lose romance points if you didn't get on one knee. (Note, if you are physically incapable of getting down on one knee, such as if you are in a wheelchair or are otherwise unable, you can still try to find a creative way to strike the one knee pose.)
The proposal is your first official step in what should be a wonderful, lifelong commitment. Get it right and it's a beautiful story you can tell for the rest of your life. Get it wrong, and it's a cautionary tale everyone else will be telling for the rest of their lives. How this story ends is up to you, so be smart about it.
What are relationships like in a fantasy universe? Find out in the book I wrote.