I've owned and still do own sailboats.
One of my female coworkers put it bluntly, as she is wont to do: Women on boats are meant to be eye candy. They're there to show themselves off to everyone else, and the nicer the boat the better.
You're not going to get much action with a small cheap fishing boat, but you will with a power boat or anything they can lay on and be seen. I had absolutely no problem getting women to come boating with me until I got a small fast sport sailboat. I like it for the speed and the handling challenge, which are things that don't interest most women at all.
Also, B.O.A.T. = Bust Out Another Thousand. Or otherwise known as a hole in the water you throw money into. This hasn't been my experience but I did unload my bigger sailboat before I had to deal with big ticket items, and I haven't had to deal with the nightmare of salt water.
But all that said, boats are an excellent social tool if you're willing to spend about 5k on buying it, and you have a place to store it that won't break the bank, and you have a vehicle that can tow it easily.
Edit: if you're going to buy, be very careful to learn what to look for before you ever go look at one you want to buy. You can easily blow a lot of money on a polished turd.
