Q&A with Marilyn Oliveira

What does a guy need to know when it comes to popping the question?
Marilyn: He should know that the engagement ring will be worn every day for the rest of her life and be passed down to future generations -- so he should invest accordingly. That most men still ask the bride's father for his blessing in advance; that he will probably be very nervous even if he's sure she will say yes; and that kneeling will never, ever go out of style.
Should a guy propose only when he's sure a "yes" is coming?
Marilyn: If a guy isn't sure a "yes" is coming, he should probably ask himself why not. Has he not dated the girl very long? Are there big issues between them? If the answer to either of those questions is a yes, he may want to focus on the relationship for a while until he is reasonably confident that an engagement is something they both want.
What type of setting works best for this kind of moment?
Marilyn: A setting that is meaningful in some way to the couple works best -- someplace that has an emotion or special memory attached to it and either offers a modicum of privacy or has loved ones gathered there.
Proposing at a sports arena? Bad idea?
Marilyn: Proposing at a sports arena is a terrible idea unless the potential bride is a sports maniac obsessed with the particular team playing, and you are absolutely positive that she won't turn you down on the Jumbotron.
Any proposal no-nos guys should know about?
Marilyn: Don't stage a proposal during a wedding or other special event in honor of another person because you'll be stealing someone's thunder.
How many times will a fiancee tell her engagement story in a lifetime? Hundreds? Thousands?
Marilyn: A woman will tell her engagement story to generations of family, decades' worth of friends and coworkers, an army of acquaintances, and potentially thousands of random people via social media. Multiply those scenarios by the number of points in her diamond and you may have an inkling of the grand total.
Can women ask men yet?
Marilyn: Women can do whatever they like. Is it a widely accepted practice with wildly successful results? No.
What's the best proposal story you've ever heard?
Marilyn: A formerly dry, unromantic type completely surprised his girlfriend by arranging for a limo to collect her out of the blue and drop her at an airfield where a private jet was waiting. She was flown somewhere dazzling (Hawaii, if I remember correctly) where another car then picked her up and took her to a beach where the boyfriend was on bended knee with roses, Champagne, and a beautiful ring.
The worst proposal story ever?
Marilyn: Warren Beatty asked Joan Collins to make him a sandwich, and when she opened the fridge, there was an engagement ring stuck in the carton of chopped liver. (She accepted his proposal, but they later called off the engagement.)
Any final morsel of advice for men on the cusp of asking the big question?
Marilyn: Be prepared for lots of tears. Now, go get 'em tiger ...