Setting a wedding date is tricky, especially if you’re thinking of having a long engagement. Sure, looking 2 years out means you’re more likely to find the spot you want available on that day, but first you have to figure out the when. It’s kind of a chicken and egg thing–the where may depend on the when and vice versa.

For me, though, there’s one other bit that matters: we already have an anniversary! We met, and got to know one another, online and dated long distance for the first few months of our relationship. We’ve always considered our anniversary, however, to be the day we first met in person–Nov. 2. Mr. Road Trip came to town for the weekend and we consider that Friday, the night of our first date, our anniversary.

My dating history, by the way, leaves something to be desired. What I lacked in quality, apparently, I made up in quantity if you count all those first/blind dates that never went anywhere.There seemed to be a few pretty steady lines of demarcation:

• If we were still talking after the first date, 3 weeks seemed to be the next drop-off point.
• If we were still dating after 3 weeks, 3 months was the milestone it most likely ended upon.
• If we made it past 3 months, though (and this was rare), at a year things fizzled.
• Unless, of course, we decided to get married. In which case, we never quite made it to 3 years.

Yes, you read that right: neither of my previous marriages lasted 3 years. I also had the nickname of gypsy for a while, 3 years being the longest I’d lived in any one place and even then most were shorter stints.

Looking back I kinda have to wonder why I’ve always considered 3 my “lucky” number.

So Mr. Road Trip comes along. A bit more than 6 months after we start dating, he moves to Florida. A year after that we move in together (signing that lease was a scary thing, indeed!) and then we renew our lease. It shouldn’t come as any surprise that, as we approached that 3 year point, I was a bit nervous. Okay, I was paranoid.

But here’s the thing: we were still talking. We were more than talking, we actually LIKED being together as much as we possibly could. We’d gone on trips, even a 7-day cruise, and hadn’t needed time apart.

So, now that we’s achieved the illusive 3 years and were still going strong (a major factor in my thought process in the me vs marriage debate) I didn’t want to give up those years we’ve already logged in our relationship. I don’t want to have to pick another date and start all over at day 1 again.

I want to get married on our anniversary.

When I realized this I grabbed my calendar to check out the upcoming years. (Keep in mind, this was still pre-proposal, so I might have been jumping the gun a tad but, hey, a girl’s gotta know what she’s working with!) Turned out, November 2nd falls on a Friday in 2012 and a Saturday in 2013–perfect! And, hey, if we want or need to make it a really long engagement, there’s still a Sunday in 2014 (though I hope it doesn’t come to that, honestly–I said I wanted to try a long engagement but not that long!).

And, yes, I did broach the subject with Mr. Road Trip, pre-proposal–mainly because my head was swimming with ideas and thoughts and maybes and maybe-nots so I wanted us to be on the same page. Turns out, the way he saw it, he’d considered himself ahead of me when it came to future-thinking and my obsession has managed to catch us up to each other.

Did you have any date dilemma when planning your wedding?

Which came first, the when or the where?