Since You Asked…

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Dear Caroline,

I have been seeing a woman for nearly a year. We’re both in our late 40s, previously married, with young adult kids. I’m sure she’s the one, and I’m ready to propose. I want to make it special. I was thinking of making an arrangement at a major-league baseball stadium where I once saw a proposal during a game, hiring a plane to carry a banner over the beach or throwing a surprise party with all our friends and family.

When I ran these ideas past my sister, she shook her head and said, “Surprises aren’t good.”

What are your thoughts?

… Robert

Dear Robert,

When it comes to the “Rules of Engagement,” there are generally two types of situations. One in which the couple has discussed marriage, knows they’re on the same page and sees the proposal as an inevitable formality. And another in which the proposal may come as a surprise.

If the two of you fall into category one, meaning you know she’s expecting a proposal, will happily say “yes” and enjoys being in the spotlight, you’ll be fine going big and grand.

However, if the two of you haven’t already agreed that you’re destined to go down the aisle, or if she’s not an extrovert, a big, public proposal can be awkward, if not downright traumatic and coercive.

Only you know the dynamic in your relationship. Treat this life-changing moment with the sensitivity it deserves.

Wishing you an affirmative answer and many years of happiness,


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