The Art of the Perfect Proposal (Or: Let Me Lie for You)

“Jerry, just remember, it’s not a lie if you believe it.”
— George Costanza

I come from a long line of Irish thieves, liars, and raconteurs, who were never afraid to fight, cry, or love. Fortunately, I’ve managed to control my Irish passions enough to avoid jail and serious injury.

As a sailing yacht captain, I find myself tapping into my Irish roots to help spring the ultimate surprise on the unsuspecting “finaceé-to-be”.

I get a call at least once a week from someone planning a proposal. And almost all of them share one thing in common:

They’re terrible liars.

The trouble is, most people think they can pull it off. But their stories have more holes than a back alley in Tijuana. That’s where I come in. Consider me your Proposal Coach.

Let me guide you in the subtle art of planning the perfect surprise proposal. Or, in other words; Let me lie for you.

5 Tips That Guarantee Big Smiles, Happy Tears, and a Resounding YES!

Planning a proposal can turn otherwise rational people into over-caffeinated event producers. Deep breath. You don’t need a production crew—you need a moment that feels real.

Here’s how to get it right:

1. Keep it simple.

The more elaborate the plan, the more there is to forget. This isn’t a TED Talk. It’s one question, one moment, one answer that changes everything. Simple wins. Every time.

2. Control yourself.

We’ve seen it all—people pacing the deck like it’s a covert operation. Adrenaline spiking, hands shaking, eyes scanning the horizon like something might go wrong. Relax. If you’re acting like something big is about to happen… your partner already knows. Treat it like a great night out together. That’s what makes the surprise land.

3. Trust us.

We do this. A lot. And we’re very good at it. While you’re thinking about the words, we’re thinking about wind direction, boat positioning, lighting, timing, and where the skyline hits just right. There’s a reason the moment feels effortless—it’s not. Let us handle that part.

4. Don’t try to out-produce the moment.

You’re on a private yacht, champagne in hand, the city glowing behind you, and the ocean wide open in front. That’s already magic. The mistake? Trying to add to it. No gimmicks. No overthinking. Just show up, mean it, and ask.

5. Don’t over-script their reaction.

You’ve imagined the gasp. The tears. The perfectly timed “yes.” But real life? They might laugh. They might freeze. They might say, “Wait… are you serious?” That’s not the moment going sideways—that is the moment. The best proposals aren’t performed. They’re felt.