A: The best way to propose to a woman is from the heart. For a woman, in many ways, the words you use when you ask her to marry you will matter more than where or when you ask. Encourage your brother to have the words for the actual proposal down pat first. If it helps, he can make a list of all the reasons he wants her as his wife, and then he can go from there. It doesn’t have to be longwinded or poetically elegant, just honest.
Once he has the words straightened out, he can start worrying about “coolness.” I’m going to assume there’s a greater than average likelihood she’ll say yes, but if you have any reason to think your brother is setting himself up for rejection, then have a talk with him about whether or not this is the right move. If he decides to move forward, make sure he understands a public proposal will not “tip the scales in his favor.” Her personality needs to be taken into consideration. Does she love attention, or is she on the shy side? If she refrains from holding hands in public, a flash mob marriage proposal doesn’t seem to fit. On the other hand, if she was a musical theatre major in college, chances are a full-scale proposal would be a big hit.
What are his options? Here are some of my favorites I’ve heard over the years:
1. Take her to a wonderful restaurant, and during the meal, have the man or woman seated at the table next to you tap her on the shoulder and say, “Excuse me, miss. Is this yours? It was on the floor under your chair.” The man holds out a diamond ring. Of course, she’s going to deny ownership. And that’s when your brother can get up, take the ring from the man and drop to one knee. (Tip: Works best if you get someone your brother’s girlfriend doesn’t know to play the part of the “stranger.” Otherwise, a waiter can do the trick. Simply have your brother get the waiter alone at some point in the meal to explain the details.)
2. Jumbotron proposals are fine, but they’re not very creative these days. If your brother’s girlfriend is a big sports fan, contact your local team’s marketing department and ask if they have other options. I witnessed a proposal pre-game, during ceremonial pitches. It was done on-field, and while the entire stadium wasn’t taking part in it, people watching closely knew what was happening. By the look of the woman’s face, it was everything she dreamed her proposal would be.
3. If she loves her job or has a particularly important hobby, try to work it into the proposal. I’ve heard of classrooms of kids being enlisted in proposals, and youth sports teams doing the same. One story involved a woman who volunteered as a softball coach. The boyfriend dressed up as an overly-equipped home plate umpire, complete with an identity-concealing mask. Before the game started, the catcher called the woman to the plate, claiming something was wrong with her leg guard. The catcher dug around in the pads and incredulously pulled out a diamond ring, which the umpire promptly took for closer inspection. A proposal ensued.
As for me, four years into a grueling long distance relationship, my husband proposed over dinner by simply sliding a box toward me and saying a few heartfelt words, ending with “Will you be my wife?” I still think his smooth, quiet delivery was pretty darn cool. ☺
Whatever your brother decides to do, the key to a successful proposal is knowing the intended well enough to plan something she’ll want and enjoy. Good luck to your brother! And kudos to you—you’re steps ahead of the game.