Your wife thinks you should just sail over and talk to him.
"No, he's probably busy," you'll say. "I'd just be bugging him."
Your wife thinks that he'd probably enjoy talking to another guy who has a boat.
"It's something you have in common. You can ask him how he got so much money that he decided he'd better throw some away on a boat, then you can tell him about how you made a killing buying out underwater mortgages from families who'd been bodily removed from their homes by sheriffs."
You know your wife won't get off your back about this until you finally break down and talk to the guy, so you sail your boat next to his and you shout over to him, "Hi! I see you have a boat."
The guy will fall all over himself to engage you.
"Yeah, you too huh? How about that?" he'll say. "How much money do you have?"
Tell him exactly how much money you have, including assets and long-term investments. Tell him how much your house would sell for if you put it on the market today.
"Wow," he'll say. "We, like, almost have the exact same amount of money!"
He'll start to cry and you won't have to ask why. He feels what you feel. Relief, that finally, at long last, there's someone out there who is able to buy just as much stuff as him.
"I once sailed around the world," say to him. "I did it looking to have a conversation just like this one. Sailed around the world, and here I didn't even have to leave the marina."
Later tonight, you and the other guy with a boat will go below deck on his boat to drink some really fucking expensive brandy and talk about the most disgusting/astonishing acts you ever paid human beings to perform for your sexual arousal. Congratulations on making a brand new friend at age 51.
Happy That Guy Has A Boat Too Day!