Don't count your groomsmen gifts before they've hatched. Assumption is the mother of all screw-ups, and nothing undermines a sweetly earnest, clumsy proposal like a pre-planned engagement party jumping out clown-car style the second she says yes. As always, when it comes to women, even if you know it's a sure thing, respect her dignity and act like you don't. Once she says yes, then start shopping for groomsmen gifts.
Don't choose a romantic dinner for your proposal site. Don't hide the ring in shrimp cocktail, don't have the waiter write "will you marry me?" in the dessert frosting, and don't have your groomsmen circle the table and sing a serenade on a bribe of good groomsmen gifts. Food proposals are clichd and corny, and it is very important she has a proposal story that is different and better than all her friends.
Don't combine business with proposals. Work is where you sweat and toil forty hours a week so you have the money for a nice wedding and groomsmen gifts. It is where you got a painful paper cut and where your boss chewed you out for not replacing the printer paper. No matter how magical the proposal, it is impossible to get in a romantic mindset amidst the smell of scotch tape and coffee dregs. What's next, three ring binders as groomsmen gifts? Even if you met at work, leave your daily grind out of the special moment with a sweet, escapist proposal.
Don't buy the ring in advance. Engagement rings are a lot more complicated than your garden variety groomsmen gifts. Cut, color, clarity-it's just too confusing for the average man to contemplate. Make yourself and your future wife happy by proposing with something creative and vaguely circular-a dollar folded into the shape of a ring, a tab from her favorite soda, a family heirloom ring. A mushy placeholder is the perfect prelude to the more permanent ring you let her choose herself!
Don't look to your friends for advice on how to propose. Get advice when it comes time to buy groomsmen gifts, not when it's time to pop the question. Instead, plan your proposal based on something personal to you two. Propose at the place where your car broke down on your first date, or in "your" video aisle where you first discovered your mutual passion for Monty Python movies.
