I’ve developed a reputation among friends as a sailboat matchmaker. It often begins with an irrational text message: “I found an amazing boat. Almost free. Needs work. I should get it, right?”

Thank God for the thumbs down emoji.

And thus, the real search begins. After all, your life is about to change, so let’s choose well. I share these five matchmaking principles with every aspiring friend.

The First Principle: Since you will spend the most time in the cockpit, select one that mirrors your personality. Are you an introvert with plans to always sail solo? Then think of the cockpit as your cocoon. Plan it as you would a she-shed chaise lounge. Make sure you can see and reach everything and that you feel secure and empowered in it.

However, if you hope to attract friends via sailing (or already have a few willing to go with you), then make sure to have space and amenities for all of them.

The cockpit is the family room of the sailboat, so seek family room amenities, like cup holders, back rests, foot rests, a cooler and a subwoofer. You can’t go overboard in the quest for the perfect cockpit. I know a popular ska-loving sailor who once bought a boat because the cockpit made a suitable mosh-pit.

This may seem counterintuitive considering the First Principle, but the Second Principle is to seek and find the smallest boat that will do the work you need it do. One friend in his 70s told me  that he has owned five trailerable boats in 60 years. When he and his family crew can’t sail in the Wisconsin winter, they tow the boat south. He laments the McMansion fleet filling marinas like former farm fields and rarely sailing. If the crew must wear headsets to communicate when docking, a boat is too big. 

In fact, a boat under 30 feet is much easier to sail often with friends than a boat over 40 feet and the speed difference is nominal. You’ll outpace both small and a large sailboat routinely while riding your bicycle. And you’ll sail a small boat longer into the future.

Third Principle: Go for maximum headroom, but not the kind you’re thinking. Yes, headroom below the deck is nice to have, but sailplan headroom is how your boat will come to life and your relationship with it will evolve. Sailplan headroom is about having reserve capacity and the room to grow. So find a boat that can carry more sail area you think you will regularly use. Go for the tallest rig, the longest boom, the most roach, the greatest headsail overlap, a staysail and the biggest spinnaker or gennaker you can fly. Of course, you don’t have to set all this cloth, but when the breeze inevitably lightens, you and your crew will thank me. When it pipes up, reef and furl. This is the key to making sailing exciting and fun in all conditions.

Fourth Principle: Seek balance, not volume. Great designers draw boats that appear to sail themselves and then do it (only needing you to point the way). Beamy, fat or tall hulls with short stubby rigs need ideal conditions and, like a mule, must be coaxed to move. Once going, they’ll roll and bounce more than they slice and track. If a sailboat looks sleek and elegant, it will sail sleekly and elegantly. If it looks muscular and lean, it will sail with power and force. If it looks stubborn, it will be.

Fifth Principle: Listen to your heart but trust your mind. Remember when you fell head-over-heels in love with your soulmate? Their very presence elicited a sweaty, breathy nervousness, butterflies and the anticipation of endless time together. Remember when you saw your love in a crowd and felt called to them while the rest blurred into the frame? You should feel the same singular magnetic attraction to your sailboat.

Love is blind and so is desire, so as your matchmaker I will remind you to pause and ponder long enough to distinguish between a crush and a passion. One is fun but ephemeral and might come back to haunt you. The other is unforgettable, transformative and will last forever if you let it. So study your feelings as you would when considering a marriage proposal. You’ll know.

But just in case, your matchmaker will confirm with a “Couple with Heart” emoji.