A good friend once told me: "Everything you have before a relationship comes into the relationship as baggage. Once you are dating, she has to approve of any big decisions you want to make."
In other words, if you want to live on a boat, do it while you are single; that way the boat comes into the relationship as baggage.
Maddie has often told me that if we were in a house and I proposed the idea of living aboard, she would have laughed and said no. Since I already lived on Wisdom, the step was already made and she had to move aboard if she wanted to be with me.
I knew from experience that this was true. When I was in dental school, I lived in an apartment and dreamed of living on a boat as soon as I graduated and I wasn't going to let anyone take that dream away from me! While dating, the conversation of "where do you want to live after you graduate?" would always come up. The girl I was dating at that time would already be picturing her future married to a dentist, living in a fancy neighborhood in a house with a white picket fence. I would tell her that I'm going to live in a boat and her face would drop! Their dream house with its white picket fence does not float.
She would then assume that I was referring to a massive yacht that resembles a floating palace and once again be ok with the dream until I showed them the bookmarks I had on www.yachtworld.com.
My plan was to buy the smallest, cheapest piece of crap that floated to get out on the water and start saving money to buy a real boat. I knew that if I stayed on land I would have to pay rent which could have been money saved towards my future boat!
Since I wanted to make the move instantly, I was looking for a boat that was close to one months rent ($1,700). In other words, rotting pieces of plastic that were around 20 feet in length. They were all small, dirty, and very cheap!
This conversation would typically only come up once, because she would then leave in search of another guy who wants to buy many expensive things and live in debt for the rest of their lives.
This situation repeated itself with every girl I dated. Soon, it became a game to me. How small of a boat would she accept before running away? I would show them 40 foot boats, and then move down to 30 footers that were less expensive, and then 20 footers that were nearly free! I would gauge their responses on clean vs dirty and how many rooms the boat had.
Girls typically seemed ok with a 40 footer that had at least three staterooms, modern looking, and very clean. These boats were also in the price range of $200,000. Way out of my budget.
I used this conversation as a screener for the girls that I dated. I grew up in Puerto Rico and went to a small private school where the girls in my class were so stuck up and materialistic that it disgusted me. The last thing I wanted was to be stuck with someone who, under the surface, was actually like those girls. I can guarantee you that none of my high school classmates would have been willing to live in a sailboat, and neither would a stuck up materialistic girl in Maryland (where I was in dental school) .
This conversation quickly evolved from "the end of dating that girl" to "the test to see if you are the right girl". In the same fashion, the conversion came up earlier in the relationship to reduce how much time I would be wasting.
I figured that if I could find a girl who was as excited about living on a sailboat as I was, she would be the right girl for me. But I never did meet a girl like that during school.
When I graduated, my search for my first boat evolved from combing through yachtworld to calling up the listings to go see the boat.
The girl I was dating at the time thought the idea was "cute" and never said more. I thought this meant that she was on board with the idea! I went to see an S2 (28 feet) which was a complete wreck for $1,200. I figured I could camp in it while I saved up! The broker took forever to get back to me, making me think I should continue my search elsewhere.
I went to see an Irwin 32 for $5,000. It had plenty of space! Forward berth, quarter berth, galley, U shaped salon, the works! The only catch was the previous owner used the boat as his storage space. To make more room, he stripped all the paneling off the inside! This meant the boat has a lovely orange wall with roving texture. I offered half ($2,500) on the boat and the owner counter offered with $3,000. I was not about to spend an extra $500 on this floating storage space!
My dad gave me some interesting advice: "Take the asking price on this boat and add how much would you spend to fix this boat up to your standards? Then add one years rent to that number. Now add a years slip fee. Now look for a boat in that price range!"
One years rent was $20,400.
The boat was asking $5,000.
I wasn't going to put any money into it because it was a stepping stone, $0. My dad insisted that I would easily spend $10,000 bringing any boat up to living standards. For fun, we added that to the mix, $10,000.
The marina I wanted to live in was $107 per foot, or $3,424.
This all added up to: $38,824.
Now that we had a number it was time to look at some boats on yachtworld!
The jump in size and quality was amazing going from under $2,000 to $38,000! Most of these boats were all 20 to 30 feet long and rather well kept, and then I saw Wisdom listed for $39,500.
She had long overhangs, full keel, and was 45 feet long! I called the broker and went to see the boat that same day! I took pictures and fell in love. This was going to be my home!
When I got back to my apartment, I showed the pictures to the girl I was dating who previously said the idea was "cute". Turns out "cute" meant "no, but I don't want to discuss it because I'm sure this is just a phase you are going through." She gave me an ultimatum: her or the boat. That was one of the easiest decisions I have ever made.
After a survey and sea trial, I bought Wisdom and moved aboard. I was single again and the search for a partner became more entertaining.