Photo by Leon Biss on Unsplash

Sum of my Disappointments

Megan Jessop
7 min readFeb 20, 2018

Sometimes it’s hard to know what to do when things don’t turn out the way you’ve expected them to. Lucky for me, it seems like I’ve had a lifetime of learning to train myself in being adaptable in this area. Perhaps the number one cause of disappointments is because I get it built up in my head that things should be a certain way and when they don’t turn out as expected, I get bummed out.

It’s been a little over a week since I was given this challenge and well… there have been disappointments. I am learning a lot about myself in the process. Before I get too far ahead of myself, I should say that this past week was a bit of a roller coaster ride in this whole dating thing. Perhaps one of the biggest things I am finding is that online dating sucks. Big surprise, right? I know. Depending on the app you use, most seem to be looking for hookups and given how self-conscious I am about dating in general, I am definitely not in a place where I want to “Netflix and chill” right off the bat! It feels like most guys I get matched with either message me sexual invitations or they don’t message me at all. When I take the initiative, they don’t message me back.

There have been a few decent prospects though! Perhaps I am old fashioned but in my experience, it makes a girl feel pretty special when she’s the one being pursued rather than the one pursuing. But I’m also all about challenging gender stereotypes, so I’m not above being the one to engage in the conversation first… it just takes getting past the initial sense that I’m not good enough for the person I’m attempting to connect with… I’m pushing myself in this because, well, you never know until you try, right? I’ve always felt that if a person loves you they will love you as you are, right now. Yet, my insecurities often tell me a different story. I’m still a work in progress to silence those insecurities and that’s okay… as long as there’s progress.

The most surprising prospects have been those that I figured were out of my league and I said no to but they messaged me anyways. There was one beautiful example of this last week. We’ll call him Mr. Enneagram, because his opening line appealed to this passion of mine. This pretty much proved that he was already winning. We had a wonderful conversation through most of the week where the conversation spurred on from my interests in psychology to books and cooking… the man even offered to help me fix my car! His genuine desire to know me and be kind to me was awe-inspiring. The downside? It was easy to get my emotions involved. When he asked me out — first to dinner on Valentine’s day (How’s that for ambitious!) which I had to decline due to previous plans made over a month ago with my sisters — we settled on coffee in one of my favorite downtown shops. I was excited.

Photo by Dapo Oni on Unsplash

Now, I enjoy enjoy butterflies as much as the next girl (probably more, if you really know me!) but I was constantly trying to talk myself down from my expectations of what this date would mean. He kept messaging me and being super sweet, so that certainly didn’t help, but I can’t blame Mr. E for that! When the day came to meet up, I messaged him my phone number in case something came up where he had to get a hold of me and that’s when I was hit with it. Disappointment. I don’t want to get into the details here because that is his story to tell but he very respectfully told me that someone he’s always had a thing for came back into his life unexpectedly and he wouldn’t feel right pursuing me until he knew where the other relationship would lead. He offered to still grab coffee as friends but would have to be another day due to family stuff that came up.

Bummer. I took a deep breath and calmly told him that I was disappointed but understood the dilemma and appreciated his honesty. I declined the rescheduled date because I had to dress shop for my best friend’s wedding the next day and didn’t see the point of getting my hopes up. I told him if things didn’t work out the door was still open, depending of course of how things turned out in my life as well. Talk about bad timing. My first thought was to buy a bottle of wine and some ice cream then spend the rest of the night cuddling with my little sisters watching Dirty Dancing or something. Those plans were short-lived due to my sisters’ advice that wine would be a bad idea considering I still had to drive 50 miles back to my apartment that night in a snow storm. I settled for a simple episode of Sherlock with them instead and bypassed feeling sorry for myself as I drove back home.

So, I’m growing! Now, I will attest that the disappointment might have been a little easier to take had I not had a terrible night previously. Per the advice of one of my friends, I was playing the field and attempting to go on multiple dates at a time in order to not put all my eggs in one basket. She said this would be helpful to not get my emotions too involved… which clearly is advice that I need. So in the spirit of applying said advice, I was messaging back and forth with another guy who claimed to be a good man with Christian values. I was hopeful that this guy would be someone who could understand both my very spiritual tendencies but perhaps also understand my struggles with the religion and the church… again, you never know until you try… so I gave it a shot. Within a couple hours of messaging back and forth, the guy was asking me all about my very personal sexual history, some of which consists a significant amount of abuse and exploitation. I need not get into details. In spite of my insisting that the conversation made me very uncomfortable and attempting to change the subject, he continued to press the issue, asking the same questions in different ways. He kept bringing it back to the importance of saving yourself for marriage and being pure… yet I have never felt more broken and shameful in my life. I hate the fact that fundamentalism and purity culture have made this sort of behavior okay. Gentlemen, let’s get one thing clear right now… it’s not.

The same friend that gave me the advice to date multiple men until an actual relationship was discussed, also gave me some valuable advice that was ringing in my head that night. She told me that the right kind of man would make me feel cherished for who I was as a person. Honestly, once I stopped responding to the messages, I knew one thing. The way I felt in that moment was the opposite of that. Sleeping in my sisters room that night, I cried myself to sleep. I felt so low and so embarrassed that I would wake her up with my drama. Thankfully I didn’t. The thing about this encounter was that he treated me so starkly different than Mr. Enneagram had all week. The hope that I was holding onto was that there were better men out there and I had a date with one the following evening.

The thing is, after some time of grieving the fantasy world I had built up in my head that Mr. Enneagram was the perfect gentleman (I still believe he was), I realized that it really didn’t matter. What mattered was the fact that there are still good men out there and I can’t give up hope that I will still meet one of them at some point along this journey. If I don’t find he’s that type of man, I’ll block him just like I did the last guy and move forward. In the midst of this whole mess, I realized that my sisters were watching me and taking note of how I was dealing with each challenge. I realized that if nothing else, the ability to know that I was worth more than what some asshole made me feel and more than the sum of my disappointments, along with the ability to be that examples to my younger sisters, was something I will not take lightly.

Photo by Peter ᴳᴱᴼ Kent on Unsplash

Yes, it has been difficult to not get down when things aren’t what they seem to be. It’s hard not to be a little depressed when the date you were looking forward to is cancelled and it seems like crickets are singing in place of the notifications on your dating apps. There’s still time before March 15th and this sure as hell is not the end of the road. In fact, over the course of the weekend, I now have not one, but three separate dates next week. Things do look up in time. Honestly, it’s been a fairly quick turn around, if I do say so myself. Which, if I’m honest, has done wonders for my confidence. In hindsight of what was a rather odd weekend with an intricate mixture of darkness and light, I am reminded that pruning is a simultaneous cutting down in order to build back up. There must be pain in order to grow. I suppose that’s what this season is and I am finding that there is beauty in all of it.

--

--

Megan Jessop

Experienced editor with a demonstrated history of working in the writing and editing industry. Bachelor of Arts in English from the University of Montana.