Adapted from a recent online discussion.
Ultimatum doesn't get you a spouse, it gets you hostage
Q: What are your thoughts on giving a guy an ultimatum? Do you think after a certain period of time with somebody, the idea of living together or marriage should be brought up and, if not, some sort of ultimatum given?
A: My thoughts on ultimatums are overwhelmingly negative. Why would you want to marry someone you have to threaten to go along with it? And why would you want to pressure someone you love into anything (stuff that falls into the tough-medicine category excepted)?
If you want to marry someone, then that must mean you want to spend the rest of your life with him, right? If you've come to that conclusion, then do some more thinking on the topic before you say anything to anyone.
First, are you really at the point in your relationship where that makes sense? Have you seen each other through different things, have you taken note of the way you and he solve problems, are you good for each other, have you outlasted the head-rush of initial attraction? Are you gunning to marry this person because he's the one you happen to be with when society tells you it's Marriage Time?
Think, think, think, and question everything in your reasoning that resembles an unchallenged assumption. It can't hurt, and it can save you from feeling deeply stuck seven years from now.
If you're sure this is the person you want, then, next step:
Would you be okay with your relationship staying as-is "the rest of your life"?
Presumably no. So, what about your status quo do you want to change — do you want to share a home, have kids, make things right in the eyes of God, get your naggy Aunt Mae off your back, secure the legal protections offered by marriage . . . ?
Once you've accounted for the who and the what, consider the various ways to get what you want. Presumably marriage is one of them, but are there others? Are any of those acceptable to you?
After you've thoroughly explored all of these ideas, and lined up what you want, believe is best for you and hope is best for him, then you talk to him. You lay out the way you'd like things to be — barring the unforeseen, of course, as always — and see whether he shares your vision.
The conversation could end there. If you're in agreement on your path as a couple, though, then you say that you see marriage as an important step in this process for X or Y reason(s).
Should his plans diverge with yours at any point, at least consider what he wants and the reasons he gives. If you can embrace his way, then do — and if you can't, then explain that to him when you break up.
Translation: 100 percent truth, no ultimatums. It's no fun to start the conversation, but there's no "no fun" like a marriage entered under pressure.
This answer doesn't account for styles; those who have a dramatic proposal scene in mind would have a hard time with the spell-it-out conversation. As long as proposer and proposee both buy into the fairy-tale staging and also are able to talk freely after, then, mazel tov.