A couple of days ago, I gave some details about our Maui vacation. However, one point that I glossed over was that my wife and I own a timeshare.

Yep, one of those things that the financial professionals tell you never to buy.

I don’t know if I’ve written the back-story to how the timeshare came into our lives, but I think its an interesting story and I hope that someone will learn something.

In early 2004, I experienced a month of unprecedented success. The technology bust was starting to end, and I got a software engineering job with a company filled with people who I had worked with very successfully before. Soon after, I started a very interesting woman. I knew it had potential when she felt the same way about Derek Jeter that I do. (Hey we’re both Bostonians!) We had been dating for about 6 weeks when a buddy of mine said to me, “Hey the wife and I have the 2 bedroom timeshare in Aruba reserved for late October. It’s too much space for the two of us, perhaps you’d like to come along with your new girlfriend?” I knew it was a little early to ask about vacation plans, but late October was still a good 5 months away. I decided to cautiously approach this woman I had been dating about it, with the idea of, “Hey this offer is clearly contingent on us being together at the time. However, at that point we’ll have dated 6 months and it isn’t so weird.” My friend understood from the outset that it was going to be difficult for us to commit then and there, but he left it as an open invitation.

Fast forward to around July/August timefame and we realized it was time to book the tickets.

The woman I was dating wasn’t sure what to make of Aruba. She had heard stories about some places in the Caribbean that aren’t as flattering when you leave the resort (I’ve heard this about Jamaica a few times.) However, Aruba surprised her as just being a great place. It was clean, good beaches, the Marriott where we were staying had a great pool. The weather was fantastic the entire time. Pretty much everyone was from New York or Boston. There were enough Bostonians that we dubbed it, “South, South Boston.” It was a homerun of a vacation.

The vacation was going so well, that my girlfriend and I went to the timeshare presentation. They usually give you around $100 in gift certificates for a local restaurant for an hour of your time. That seemed like a good to me so we took it. (Note: this will be analyzed in more detail in a future post.) It was a “WE” because even though my girlfriend and I each earned a good income at the time, they gear the offers to couples… and they heavily prefer them to be married.

We took in the information about the timeshare and, as salesmen are paid to do, they made a good case for timeshare ownership. As we were just dating each of absorbed the information differently. After the technology bust, I didn’t have the disposable income for it. However, I had been to the same presentation 4 years earlier with another friend and the property was around $14,000. This time it was $19,000. This made me feel like I was missing out on a good investment which lead me to think that the $19,000 price wasn’t too bad and the property would only be worth more in the future.

My girlfriend, on the other hand, was in a different economic situation. As a pharmacist, she didn’t go through a technology bust as I had. In fact, her position with the military had quite a bit of job security as well as 6 weeks of vacation. She also had gotten a recent promotion. When you think about it, she was close to the ideal candidate to buy a timeshare. She had the vacation time to use it an the money to buy it. I supported it because it made sense to me.

The question was, “Is it a smart decision to buy a timeshare?” There’s a big stigma against buying timeshares. I think that investors in the 80’s got in and were burned. However, with huge companies like the Marriott offering deeded timeshares, it looks more interesting.

In the end, my girlfriend made the call to buy the timeshare.

Slightly more than one year later, my girlfriend and I were on another trip to the Caribbean. The marketing in airports on trips to the Caribbean pitch their jewelry (perhaps in an attempt to appeal to people avoiding use tax). My girlfriend jokingly put those advertisements on my lap a couple of times as a not-so-subtle hint. What she didn’t know is that each time she slapped my lap, she hit the engagement ring that I was carrying.

That girlfriend became my wife. And with that we have a timeshare.

Was it a wise decision? In 2004 (years before I would start Lazy Man and Money), it seemed like an appropriate choice. In upcoming posts, we’ll break it down in more detail.