January 21, 2014

My Best Roommate & My "First"

After being challenged by Oliver from OXYMor(m)on, I decided to share how I met my former roommate Alex, who also was my first. Yes, that "first".

I was living in Portland and had just moved to my very first place. I was riding the Max (the light rail in Portland) heading downtown to meet a friend. I go on the train and sat in my usual seat. I had a usual seat because I had figured this one seat provided the most optimal people watching location. I did the initial assessment of who was on the train and noticed, seated three rows in front of me were two guys.

One of the men was very, obviously gay, I could just tell. There was no doubt. So I watched the other guy with him and they seemed to be good friends, maybe more. This other guy was gorgeous, he was latino with a beautiful face.

I am not one to act on guys I am interested in. I am timid and shy. However, something inside me burst with courage and I stood up, walked up a row and sat down. This put the two men just two rows in front of me and gave me a much better view of the cute latino.

After watching these two for a while I assumed the latino was the other guy's boyfriend. Normally this would put an end to my curiosity, but I don't have to stop looking right?! So I kept stealing glances and the latino kept catching them and reciprocating. I took note of his ring, which was a three finger ring. I thought it was pretty cool and it stuck with me.

Finally the train reach their stop and they stood to exit. The latino looked at me as they walked past and smiled. I shyly smiled back. They walked off the train and were about to cross the street and again the latino meet my eyes and smiled—I returned the smile. That was that and I went about my day.

After I returned home that night, I decided I might as well try something I had often made fun of. I liked to read the Craigslist "missed connections" because they were hilarious. So I decided, "eh, what the heck, I'll post one for this latino." I described the missed connection and asked as a robot and troll check for him to describe his ring, as that was unique enough for only him to know and verify—if he would even see the post.

It wasn't a few hours before I had a new e-mail in my inbox. Someone claimed to be the latino and said his name was Alex. He correctly confirmed he had been wearing a three finger ring and thought I was cute and would like to meet. We exchanged a few e-mails and set up a little get together with his roommate (not boyfriend as I had thought on the train) and a friend of mine.

So we had a little get together, but get how cheesy I was. I got chips and dip and put the chips out on my new square white plates and did a little presenting with the goodies. I was nervous and excited ok! Alex and his roommate came over and we all chatted. Luckily, Alex's roommate and my friend got to talking which let Alex and I chat. When they left, Alex almost immediately text me and said how much he enjoyed the get together, but had one request for the next time, that it just be the two of us.

Alex came over a couple days later where just he and I got to chat alone. It was then that I discovered Alex had a boyfriend. I wasn't sure what to think about this discovery. Alex explained that his boyfriend lived in Australia and that they had an open relationship, so he was allowed to meet and even date guys. I could sense he was truthful and genuine and so I decided I would be ok with this. He was going to be moving to Australia in a month anyways.

Alex was my first. While I don't want to get into much detail, let me just say I wasn't ready for it. I didn't really know what was happening before it was all over. Though he was very comforting during my mini melt down Alex did have had a very flippant attitude towards sex in general. This hurt, because it was my first time and it was suppose to be special but Alex told me, "everyone has sex, it's no big deal". I told him I wanted it to be a big deal.

Aside from the unsuspecting first time, Alex was a nice guy. For example, I had missed a flight and had a rebooked flight early the next morning. Since I didn't have a car, Alex volunteered to stay at my place and drive me up to my early flight.

A few days before Alex left for Australia he said that we should stay in touch on Facebook but he was going to be with his boyfriend and thought there might be a strong future there, so any relationship we might have had should just end up as being friends. I agreed and said my goodbye.

A year later, when I was moving to a new apartment and was seeking a roommate on Facebook, Alex responded. He was moving back to America and needed a roommate as well. We became roommates, but Alex would only be in the apartment for a few months before flying back to Australia to see his new boyfriend. He wanted to keep his half of the apartment to have a home base, so I had an apartment all to myself for half a year with half the rent being paid by Alex. It was the ideal situation. Alex and I became really good friends while he was in America for those months (just friends and nothing more).

Eventually Alex and his new boyfriend started traveling back and forth between Australia and America keeping their share of the apartment, which was now a three way split on the rent. It really was the best living situation. Two guys I got along with really well, sharing an apartment for a few months and then I had it all to myself for a few months, while still splitting rent. Ideal huh?

When Alex and his boyfriend decided to move to Australia for good I was sad. I had to find a new roommate which turned out to be a horrible experience and I ended up leaving the apartment and moving back home. Alex and I are still Facebook friends today and catch up on each others lives every few months. And to think it all came from the Craigslist "missed connections".


  1. I get what you mean when you say you really didn't know what was going on before it was over. The good thing is that it was with someone you already knew instead of a complete stranger.

    1. I am very glad it wasn't with a stranger, but I am still disappointed it happened with whom it did. Not that he's a bad guy, I just was hoping it would be with someone I had more history and connection with. Someone who meant more.

  2. I love this story. It made me smile and frown and laugh out loud and sigh. More of us should tell stories like this. You're the leader here. Hows about you set that up? haha ;)

    1. Quite a range of emotions! Thats great. I wouldn't even know how to set something like that up.

  3. Haha, I've done the "presenting" the food thing. It's kinda funny.