The Enviable Dater

Usually, click-bait titles bother me but when it's for my own personal gain I've decided I don't mind it. Looking at the title of this post you probably think I am going to tell you about losing my virginity. But that’s just the tip (pun intended) of what I’m going to talk about. What I am going to talk about in this post is my first kiss, first relationship, the first time I truly committed to something and I guess my first time. But let’s start with my first kiss.  As I’ve said before I was a bit of a late bloomer. After growing up in a strictly religious family I found myself at the age of 21 having never kissed a guy and in the middle of a bit of a quarter-life crisis. I didn’t know who I was, or who I wanted to be and after 3 years living away from my parents, I had moved back home to finish university. This was frustrating, to say the least. So I did the logical thing anyone would do, I lived out my rebellious youth at an older age. A little less rebellious c

That is the Question. For the past year I have been the guy who shy's away from the committed relationship. I did not want to have to factor someone else into my life. I was having a hard enough time deciding what I was doing, let alone asking someone else for their opinion. However, I have recently come to the conclusion that I am open to commitment once again. After all, I shouldn't deprive someone the wonderful experience of dating me! Which brings us to now, I am currently at a precipice. I'm at the point of a relationship where I don't know whether I should push the guy I am dating to make it an official relationship. My question is 'Will this mess things up?'  The fear that I think we both have, as we have discussed it, is that by committing to making our relationship something official we are also committing to trying to make our relationship work despite the fear of impending failure. I think the reason why a lot of relationships fail is simply t

I'm not sure if I've mentioned it but I live in a relatively small city (pop. 58, 220). With that 'small town' appeal comes a small community of gays which I call my dating pool. It's the kind of place where every gay knows everyone else and the six degrees of separation turns into two. Earlier this summer I experienced just how small my dating pool was. I'm usually the type of guy that when I really start to like someone I limit myself to only dating them. Earlier in the summer I was enjoying the life of a casual dater and I had narrowed my prospects down to two guys. These two guys were pretty much opposites, the only thing they had in common was they were both tall. One guy was Outdoorsy, he worked as a roofer was muscular bearded your dream Canadian Lumbersexual. The other guy was materialistic, stylish, metrosexual, worked in retail and always looked perfectly put together but also casual. I had been on a two dates with both of these guys and wasn

Besides the daddies and twinks, my dating life has seemed to had a recent influx of sexually inexperienced men. One may think that sexual inexperience goes hand in hand with a young age, however, this is not the case in these situations these men are all close to my age yet still seem to be navigating the dating pool with their v-card completely intact. As someone who was a late bloomer themselves I sort of understand what this is like but now that I am on the other end of the situation I find myself feeling a bit awkward about taking someone's virginity. I hope this post does not make me seem insensitive to their situation. As I said I myself was late to the party having only lost my virginity myself at the age of 22. I know what it is like to be in their shoes. I was fresh into my first relationship and although I had done some things sexually I hadn't gone through with the final act. By this time I was at the point where I couldn't simply have sex with a stranger becau

A great date just to get ghosted! Of all the dates I've had in the past month three really stand out to me. I call them the Daddy, the Twink, and the Holy Ghost. In my opinion, I would say that each of these dates actually went well. However, in the aftermath of these dates, you wouldn't think so.  Let's start with the Daddy. Now I'm a weird age at which both older men and younger men seem attractive to me. Maybe this isn't something specific to my age demographic but I have found that recently it's become very prominent in my dating circles.  So the first guy, let's call him Bruce, was in his late 30's. He was quite muscular and bearded; which I am definitely into. Bruce asked if I wanted to grab a drink with him. So we went to a local craft brewery and the drinks started to flow. I learned quite a bit about Bruce and we were getting along okay but there didn't really seem to be a strong connection between the two of us. I still enjoyed my