You, Me, and the Roommate

by Mike Olsen 2 years ago in dating

When all else fails, delegate.

You, Me, and the Roommate
Chocolate Milk for Adults

Let's get this out in the open first. I have always been a hopeless romantic that falls hard and fast. I've dreamed of finding that perfect someone and starting a little hipster family in a perfect little city with hipster friends and disgruntled extended family who clutch onto their traditional ways of life. Openly longing for a family isn't necessarily common for a young millennial male specimen as myself. I am a man, I am proud, I am not ashamed of wearing my heart on my sleeve. I wanted love and I wanted it so badly, but I also have a horrible tendency—I have a track record of dating extremely unstable people.

It became my tragic flaw. I would meet a girl, I would share my feelings, I would win them over, and they would reveal their psychosis, and I would take the closest exit route. My sweetness (so I've been told) became the catalyst for emotional and mentally draining heartbreaks one after another. I know it takes two to tango, and pointing fingers has reverse effects, but this was getting out of hand. Yes, I know—I have my own imperfections and issues, and judging others on their problems is unfair, but I think this experience might justify my stance.

So I took a break, focused on my education, met a girl online, regretted it, and found myself halfway through a degree and single with very little hope for the hopeless romantic side of me to hold on to. I was discouraged, and was starting to feel I would have to accept the enviable reality of perpetual bachelorhood. I continued to put myself out there, but I was drained from the aftermath of past relationships hitting the fan.

Until one fateful game of Apples to Apples. I clicked, dare I say flirted, with someone new. She was great, and I felt impressed that I should get to know her better, a game of Apples to Apples only goes so far. We exchanged numbers and before you knew it I had set up the date of dates. We had a lot in common, and Halloween was around the corner. The plan was simple: Halloween Dance and late night snack run, followed by a following weekend date for dinner and... wait for it... a concert! How can you beat that?

We met at the dance, and it became obvious that Halloween Dances were not a great place to get to know someone you have only really talked to over text. Dances wouldn't be much of a dance with out really loud blaring music, which makes having subtle conversations basically impossible unless we left. However, since we both put a lot or work into our costumes, it would have been a waste to leave at this point, especially since it wasn't actually Halloween and walking around the neighbourhood would have caused a few eyebrows to raise. So instead, we yelled at each other for a few hours over the music.

Time to redeem myself, once the dance had come its long awaited end, we went out for some quick food and finally have some time to really talk and get to know each other. How wrong I was, we didn't talk. I talked, she just sat there giving one word answers to everything I asked. My plan to communicate, and have a causal conversation, turned into a personal interrogation by me. She either didn't know what to say and let me do all the talking, which I learned was something I would do when I have to hold up the conversation alone. I might as well been talking to myself the whole time. Neither one of us drink, so she ordered a juice and I ordered a chocolate milk. For the first time of the night, she asked me a question of her own.

"Chocolate Milk? What are you, five?"

I was stunned, I am pretty good at reading facial expressions and body language and it was clear that she was actually judging me. Now, I could take it if she was being passive or cheeky, but no. It was judgement through and through. So, I responded with, "And a half, five and a half."

Needless to say the flooding feeling of awkwardness hit us and the only thing we could talk about is how weird we were, in a very awkward way. We pushed another half hour out of our night and then we said goodbye and confirmed plans for our next weekend. The date turned into more of a business meeting and we were confirming details and figures like two lawyers disputing in court. This night did not go well, but what I wasn't aware of was how much worse it would get.

Six days later, we went out for dinner before going to the concert. It didn't matter whether or not she was much of a fan of the band, I knew it would be a good time regardless. So, since personal get-to-know-you questions weren't her cup of tea, perhaps a little chat on music would be. It was like pulling teeth, I could tell she was uncomfortable but I still wanted to make the best of the night. It felt like she had a secret the entire dinner that she wanted me to figure out. Something she was dangling over my head, something she wasn't sure if she would tell me or not. Normally, I would have found this intriguing, but this felt more cruel than flirtatious. That initial spark we shared over Apples to Apples was gone and we both knew it. Dinner was good, but the tension was killing me. It was now fight or flight mode, and I chose to fight for this night and date. However, she chose a mix between flight and freeze. This wasn't working, for either of us. I needed to clear my head, so I excused myself to use the washroom. It was time to psych myself up again, get my head in the dating game for the second half. I went back to my table with a new sense of confidence, game face on. I sat down, and concluded that we should probably head out for the concert and that I would get the bill. As the waitress came over, she handed my date what I thought was the bill and told us to have a great evening. I told her I would get it, but my date told me it was all good. She had already paid the bill while I was in the bathroom intentionally and just took her receipt. Maybe she could claim it on her taxes. No better way to burst a man's ego than to pay on the first date. Good grief. I was emasculated and a bit embarrassed. I thanked her and she acted like it wasn't a big deal, but it was to me. Although the progressive new age thinking male I was should have embraced this gesture, the traditionalist inside of me was breaking out now.

We took transit to the concert, we didn't have much to say. I tried to stay positive, but I was still a bit shook from dinner going so awry. The concert was our third attempt to have a good time together. Third time's a charm, right?

We had stadium seating with a decent view of the bands playing. Although I can't say I was a die-hard fan of the band, I was definitely familiar with the music. My date on the other hand was not. She sat the entire show with a puzzled look on her face, and when she wasn't doing that, she was watching my reaction. At this point, I had given up. I was going to enjoy the show and music. I just needed to be me. This was just one night, not the rest of my life, and if I'm going to try to find that right person for me, I had to be me. So I did my thing and sang and crowd danced and had a blast, trying to encourage my date every so often to do the same. The concert ended, we made our way through the crowd of teenage fans, and before we knew it we were heading back on transit to end our date.

I knew the date wasn't awesome, but you can't win them all. She was going with the motions of the date by this point, and I couldn't do much to change that. Maybe she was just out of her comfort zone, or maybe she just didn't like the music, but I could tell she wasn't one hundred percent invested to say the least. I asked her if she enjoyed the concert, just looking for some sign of contentment. She claimed she had and then indicated that I apparently had enjoyed it too. She then proceeded to make an analysis of my personality traits and assumed interests. She never fully expressed her own feelings, but she certainly expressed her opinion on me and my character. After two weekends together, she had collected enough data to give me a full account of my flaws and qualities as a person. I was a research subject for her pleasure. She showed very little interest in me because she was too busy trying to figure out all my complexities.

Her final conclusion was suppose to be taken as a compliment, but it was loaded with a lot of subtext. "You know, you should meet my roommate. You two have a lot in common. I think she would like you."

Stab and twist.

Our date ended, we probably hugged—I don't remember much of the rest of the night to be honest, I was still stuck on being handed off to some total stranger. I told her I had a great time and that she should text me once she got home to let me know she made it safely, since she and her roommate were living out of the city a few hours drive, and I was still determined to be a thoughtful after being utterly dejected.

I went back to my place, trying to shake it off by not talking about it with my own roommates and went to bed after mindless scrolling through some form of social media. I was completely friend-zoned, and that was that. I had just accomplished to carry out the worst date of my life.

Nothing could have made it worse, other than getting a direct message from the roommate a day later inquiring of my mental stability. Turns out, I just might have been the crazy one. It really truly wasn't the all the girls I've dated all this time, it was actually me all along. I sat there, looking at the screen on my computer, rereading her message and trying to figure out the connotation of it. Was she seriously asking me if I was right in the head? Jaw dropped and stunned, I decided to respond. Why not? My date's roommate wanted to know my deal, and not knowing what she knew about me already I told the truth.

Five years later, that same roommate and I are ecstatically married with one beautiful daughter and a second child on the way. At the time, my now wife had no idea that her roommate was on a date those weekends and was when she finally learned of it, she had to get the details. She found me and started the conversation. Her inquisitive nature was refreshing and it was nice to have a good conversation at last. I guess there is something to say about hitting rock bottom.

Mike Olsen
Mike Olsen
Read next: 'Chocolate Kisses'
Mike Olsen

Write what I think and I think what I write. All good things, all good things - most of the time.

See all posts by Mike Olsen