QUESTION PERIOD: How to deal with relationships and dating?

Given that Valentine's Day is coming up (February 14th), I figured that a QUESTION PERIOD post should address Valentine's and how we celebrate in Vancouver. I already gave you a list of the most affordable (and nice) restaurants to do Valentine's (in my humble opinion), and now for QUESTION PERIOD I'm going to ask you - how do you deal with relationships and dating? This is a question I have been asking myself, but with a recent post by Tanya (aka NetChick), I was reminded of the issue, and thus I thought I'd use this as a lead in to the post.

Having been single for over four years now, it's kind of interesting when people ask me if I am in a relationship, or whether I'm dating anyone. I have been in complicated relationships before (a term I commonly use for those is situationship -- although I did not coin the term itself). Recently, because of conversations with very close friends, I've started to reflect and think about the issue. Not in much depth, truth be told. But just began thinking about it again.

I haven't paid much attention to dating as I've been lucky in that I get many of the perks and very few of the problems when I'm in a situationship. Don't get me wrong. I am a very loving guy, and for sure enjoy the idea of a life partner. There are complications to being in situationships too. But if I were to really buckle down and get serious with dating, there are still a few things that stand in the way, at least at the moment.

First, I need to find myself a job that will pay for the kind of lifestyle I want. Having a romance at this moment in my life is therefore pretty secondary. Second, I want to make sure to be in a relationship for the right reasons. I don't want to be attached just because I am alone (and trust me on this one, I am NEVER alone -- my weekend fills by Tuesday morning and if you are lucky, I'll book you for next week). Third, I want to ensure that I am not chasing the perfect relationship. I am not perfect by any measure, nor do I want to be. I'm happy to grow with a partner as time goes by.

I've always been curious about what people think of the dating process, and particularly, of whether the fact that I've been out of practice for so long does make any difference to whether I will be able to find someone or not. Somebody told me that the only way that one can really develop the skills necessary to date is to engage in the process. I am someone who believes in learning by doing. That's the reason why I took up modeling. That's how I learned so many languages. I learned to be a bartender just because I thought I might need the skills sometime (I already have put them to good use, so ...). Therefore, my question is, should we just plunge in the dating pool just because we need the skill set? How have you dealt with your relationships? Have you faced any particular challenges?

Note - I've enabled comment moderation since a short while ago, so if you don't see your comment posted, don't take offense. I'm just a bit slow at the moment in getting through comments.