In the movies, wedding proposals often come as a complete shock to women. You've seen it: a romantic comedy with a closing scene set at a Yankees game on a warm summer night. The camera pans to the scoreboard, which suddenly reads: "Jessica, will you marry me? Love Paul," and Paul, now on bended knee, in the bleachers, pulls a perfect, large rock out of his pocket and says "Well?" Section 18 begins chanting "Yes! Yes! Yes!" Jessica says yes, though she had no idea Paul had this love for her. And so they live happily ever after...for the remaining 15 minutes of the movie.

In real life, before the proposal, you should get a good sense of whether your girlfriend digs you enough to marry you before you buy the ring. How good a sense? Real good. This is known as "The Conversation." And the answers to these questions are ones you should weigh carefully before entering into the most significant contract of your life.

The Conversation should cover, in a whole lot of detail, the following fifteen points, at least. A thoughtful groom will be able to think of a few more. In no particular order...

Are we going to have kids? Am I, or is she, going to take time away from their career to be the primary caregiver? If we're both working late, who is going to pick up our kid from day care? Will we both attend medical appointments? How many children do we want?

How is our sex life? Is it going to keep us fulfilled? If not, why not, and what can be improved? How often are we likely to want sex? (ed. - This person is going to be the last person you ever sleep with, if all goes well. Strange, we know.)

Do we like each other's family? If there are issues, is there anything we can do about it? (You are going to be spending a lot of time with these people over a lifetime, like it or not.)

How much time do we plan to spend with each other's family? Will we make an effort to be equitable about time spent, if that's something we both want? What about the holidays?

If I/you got a dream job in London, would we move? Will you resent me down the line for prompting such a big life event? What if I can't get a job overseas?

Are there personal habits that we each find annoying that could cause friction over time?   If so, are these things we can change without sacrificing our core personalities?

How will we each have our "me" time away from each other? Does one of us find this more important than the other?