With no offense to Rabbi Feldman -- who, for the record, does a great Bar Mitzvah -- I feel I have at last truly become a man. Just a few weeks ago, I successfully proposed to my girlfriend by crafting a personalized video that I played for her during a romantic trip on our three-year anniversary. And now that I'm an engagement veteran, I'd like to offer five tips for putting together your own romantic proposal that'll get you the answer you've been hoping for without disappointing -- or embarrassing -- your beloved.
1) One Ring To Rule Them All
Finding the perfect ring isn't fun or easy, but get it right it the first time to prevent your fiancee from setting it on fire and claiming that it "fell off in the stove." Listen carefully to her remarks while talking to friends and examining other people's rings. For example, I learned that my girlfriend prefers a round-shaped diamond by silently taking notes while she railed against the poor taste of The Bachelor.
You'll also want to borrow a couple of her other rings to best guess her size, and get input from someone whose taste you trust (in my case, my thrilled mother) before ultimately pulling the trigger.
2) Know Your Bride
As a comedian, I love attention. If traditional gender roles were reversed, I'd want to be proposed to in song by Adam Levine on an episode of The Voice for all of America to see. But while flash mobs and baseball stadium scoreboards are great for some, not all ladies will love a "big event" proposal. It's important to keep your potential fiancee's personality, interests, and passions in mind when customizing a unique proposal for your wife-to-be.
It's also important to gauge her tolerance or appreciation for surprises, and prepare or mislead her accordingly. In general, you want to find a balance between causing her to throw up (a likely reaction to producing a diamond on the fourth date) and yawn (a response you can count on after proposing seven years into the relationship). With that said...
At least some element of surprise always makes the event more magical, so don't let her girlfriends know a thing. The news will be so exciting that even her best bud with the best of intentions will have the potential to accidentally clue her in.
Postpone telling her parents until a week (or even a day or two, as I did) before the actual proposal. Not only does this keep your girlfriend from finding out, it will prevent those eager beavers from pressuring you (e.g. "Is today the day?" "You have the ring -- why not just do it?" "WHERE ARE MY GRANDKIDS!?!")
4) Bow to Her Makers
When the time does come to address her parents, do it in person. The class and initiative shown by asking your girlfriend's father for his daughter's hand in marriage will put your best foot forward with her family and will inevitably make the engagement process much smoother. It may have taken a few extra hours, but being able to address my sweetheart's dad eye-to-eye made my intentions clear and conveyed how dedicated I am to this woman. If your future father-in-law has any reservations whatsoever (hopefully due to natural parental attachment and not because of the liquor store you robbed last year), this will help assuage his fears.
Hopefully your in-laws are people you're fond of -- but even if they aren't, make sure that you reach out to them after the cat's officially out of the bag. It'd be great to plan for a celebration brunch or dinner within the next day or two. Then cross your fingers and pray that your dad and her brother don't get into a Yankees/Red Sox brawl at the table.
5) Be Ready to Roll
A married friend of mine (aka all of them) warned me that "proposing doesn't buy you any time, it simply starts the clock." But don't be afraid about planning right away -- if you're able to get on the same page as your fiancee about the general style of the wedding from the start, the engagement can be a super fun time in your relationship. Enjoy it!
....And then get back to screening those florists.