My wife had a near drowning experience as a child and had not been interested in water activities nor boats since we've been married, now over 20 years.. Here's what I did.
It took some time, patience and money, but it worked.. First, we sold the old '88 bounder RV and decided to blow the $15k on vacations..
March '04: We took the family on a cruise (our first ever) on the biggest, smoothest ship I could find (Royal Carribean Voyager of the Seas). Even in 20 foot seas we could barely feel any rocking. She loved wading around in the warm water on the beach at Cozumel and even put on a mask & snorkel for a few minutes. Great confidence builder.
June '04: I let her go to Hawaii with her 2 best friends for a week. Now she was the one who had snorkeled once before and she talked her friends into doing it there - they had a great time together. Now she was overcoming her fear of water.
Oct '04: I took her to the Lowes Resort at Coronado island, San Diego, for 3 days to celebrate 20 year anniversary. How convenient, they just happen to have a resort owned dock with rental sailboats (I knew that ahead). I picked the day with the lightest wind, hardly enough to sail, and said let's rent a boat for a few hours. She was game to humor me. It was a very gentle, pleasant sail in a Capri 22 - and I was careful to not heel over far, nor scare her. She really enjoyed it.
Dec '04: I start to hint that it would be fun to have something to replace that ol' RV, for the kids, of course..
Jan '05: I plan a "date" to a really nice restaurant, if she'll humor me with a jaunt through Portland boat show, just to look around, on the afternoon before the dinner. What happened next really was not planned at all. We met Cheryl of BWY at the show, with her MacGregor. She was so friendly, not pushy at all. She talked about the fun she's had with her kids on their Mac around the San Juans. I give Cheryl all the credit for helping my wife to understand how good a boat could work for us. We left, had the nice dinner and my wife suggested that maybe we should consider buying a Mac. Since they had a good deal going for the boat show, and since the Seattle show was starting the next week and we figured their delivery dates would get pushed out into the spring soon, we decided to go for it. (She had to really twist my arm to agree to buy a boat a couple days later.)
Feb '05: We drive up from Portland to Seattle and attend an evening Beginning Sailing seminar at BWY taught by Todd. We stay in a 4 star hotel that night and get a sailing lesson from Ray in the morning and take delivery right after lunch. The Mac now lives in the spot where we used to park the ol' RV.
Mission accomplished!
I'm taking the ASA classes now for my own good and also to build her confidence in my sailing abilities. Safety is foremost in everything. We plan to get experience this year, then next year we plan to spend some time in the San Juans.