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Feel like you’d rather pop a valium than “the question?” You poor bastard. The pressure is immense – and I feel for you. This is where knowing your intended is critical. Does she expect pomp and circumstance or would she prefer an intimate surrounding? Should you ask her father’s permission for her hand in marriage, preserving the sacred ritual and raising potential son-in-law status? As respectful as this may seem or be, this should be done prior to purchasing a ring in case you have any intention of honoring his answer if it is “no.”

Now, for “popping the question.” It should go without saying throwing the ring at her after a drunken fight is never a good idea, nor is casually asking without a ring. Regardless of the fashion in which you propose, indications you put thought into it will mean a great deal to her.

Think. What does she love? Let’s say, for example, shoes. Buy her a pair she’s been longing for. And don’t complain about the price- you already dropped a small fortune on a rock. Plan a special evening out. Just before leaving, surprise her with the shoes, kneel down to help place them on her and have the ring strategically placed in her line of vision for when she looks up.

Or let’s say her family means more to her than anything. Pick a family gathering where you are not stealing anyone else’s thunder (someone else’s engagement party or baby shower would not be opportune) and orchestrate a proposal. Perhaps you could arrange in advance for her father to ask you to “say grace” or give a toast. Make the toast all about thanking her parents for raising the woman you would be honored to spend your life with. Thank her siblings for being supportive and loving to her and being supportive of your relationship. Thank them all for welcoming you into their lives, home and hearts. Promise to cherish her as they always have and assure them her happiness will remain your top priority.

If she loves going out to dance, arrange with the DJ or the band leader, or the manager of the establishment, to play a favorite song during which you can quietly ask her for her hand in marriage, or use the microphone to publicly declare your everlasting commitment to her. No matter how you propose to your beloved, putting some effort into it can make it the legend people tell over and over and over, casting you in a glow and guaranteeing you score every time someone makes a big deal about the proposal and her absolutely perfect ring.
If she is the type to cherish every napkin, cork, memento from each date or interaction- a new trend in engagements is to hire a photographer and or videographer to record the event. It makes for a lovely chapter to add to the front of your wedding video to enjoy for years to come. I promise your children will go through a phase when they watch this every single night.

If reading this is making you wonder how to enter the witness protection program, you might want to put things on hold. Only you can determine the amount of pageantry necessary for this momentous occasion- just make sure it is consistent with her desires. I, for example, would have a freaking heart attack if someone put me on the spot, let’s say at center ice at a hockey game, and got on bended knee (unless said man on bended knew was Mario Lemeiux- then I’d eventually wake up)- not just because of the implications of being put on the spot, but being the center of attention. If it is something she normally abhors- don’t turn one of the most special moments of her life into a circus.

I can not say this enough. Knowing the woman you are about to propose marriage to should make this process pretty easy. What means the most to her- what are her hobbies? Work it in. Do NOT put the ring in a glass of champagne- if I have to listen to one more story from a girl trying to make this seem original I will leap from a tall building.