Casual Encounters

I’ve been thinking a lot about how I’d like to pursue dating after my guyatus is over.

One of the biggest things I’ve realized is that while I don’t consider promiscuity an inherently bad thing, it’s something that is not good for me.

I’ve never been a casual person. I take my job seriously. School was hugely important to me; I graduated valedictorian from high school and was in the top of my class at university. I am incredibly smart with my money and have no debt. My relationships (friendship, family, etc.) are all intense. I take so many things in my life seriously. While casual may work for some people, it doesn’t for me.

Don’t get me wrong, I am casual at times. Namely, I’ve had casual sex.

But I feel like shit after.

I’m not the kind of person that can have a casual encounter and not berate myself after. There are people that are able to do that, and that’s okay as long as they are okay with it.

So I’ve made a few goals for myself after this experience.

  1. Date around, but don’t sex around – I enjoy dating. I like meeting new people and communing over food. But I need to make sure to do it without giving my body away immediately. My counselor recommended making some platonic male friends or going on dates and JUST going on dates, nothing more.
  2. Make sure to get to know the next man I choose to have sex with – This is something that I have not done with three of the four of my partners. I went on 5 dates before I had sex with Glen. I had sex with Jake on the first date. Same with Stuart, a man I met at work. Samuel was on the second date. Again, this is not something that I think is a bad thing for other people, but for me it’s not the healthiest. My goal is to try to date someone for at least a few months before jumping in the sack. I want to really get to know someone before I have sex with them. There are two reason behind this. One being that I want to make sure that he is serious about me, that he won’t just leave after. Two being that sex is emotional for me and I want to make sure I won’t hurt myself for 15 minutes of pleasure.
  3. Have STD tests BEFORE I have sex with the next man – I am SO thankful to say that I am clean and have never had an STD. I haven’t been the smartest with protection at times. This leads me to freak out and drive myself nuts until I have the next STD screen. I don’t want to EVER be in that position again. I shouldn’t put myself in jeopardy, especially with people that aren’t even important to me.
  4. ALWAYS USE PROTECTION – Glen told me that he couldn’t have sex with condoms. This is not an uncommon trend. Many of my girlfriends have said similar things about their partners. Because Glen was my first partner and I hadn’t educated myself enough on the transmission of sexually transmitted diseases, I let it slide. I’d make excuses, but most of all I wanted him to be satisfied. Looking back, I realize how stupid that was. Unless I’m trying to have a baby with a man, I need to always demand a condom, ALWAYS.
  5. Be in a relationship with the man first – This kind of goes with number 2. Glen did ask me to be his girlfriend before I had sex with him. The other three? Hell no! They were all commitment-phobes, and it probably didn’t help that I “gave it away” so easily.
  6. Don’t go over to their place or bring them to my own – JUST DON’T. I think one of the key reasons I had sex with my last three partners was because I agreed to go to their places. Had we stayed in a public place, we probably wouldn’t have had sex. If they want to have a drink at their place, we just need to go to a bar (or call it a night).


That’s the beginning of my list. This list may look like a lot. For me, though, I think these are reasonable expectations for someone looking to move away from casual encounters.


Samuel + Realistic Expectations

Last night I spent the evening with Samuel.

I met him on an online dating website about 5 months ago. I saw his profile, and even though he was 8 years old than me, I decided to message him. Looking at his pictures I thought that he was the most gorgeous person I’d ever laid eyes on. The first thing I sent to him was a little joke, and from then on we sent long, beautiful messages to each other. On our first date, we met at a local brewery and then ate Indian food from a food truck on the street. We bar hopped, making our way back to his place.

We dated for about a month, having sex prematurely (yeah, I know). I could tell after that first time that it was probably a mistake. Samuel grew distant soon after that. He told me he was feeling depressed. Eventually (after what felt like endless prying on my part) he sent me a text message that said he would like to be friends. I was completely crushed, crying like a blubbering mess in my office at work.

I agreed to his friendship and we started doing things with each other: watching movies, making dinner, hiking. And then one night we got drunk and he said I could sleep at his place. He put me to bed (in his bed) and joined me later. We had sex that night. And then it happened a few more times after that. Initially, the sex gave me hope. I thought it meant that we had a chance.

But then I came to a realization during this “friends with benefits” period.

I deserved more.

I had sex with him for the last time on November 14th, felt super shitty after, made the decision I wasn’t going to keep hurting myself, and then started this blog.

So here I am. One month and one day since I was with Samuel. We still see each other constantly, and the chemistry is rich, fiery. Last night, walking around outside, surrounded by Christmas lights, the heat between us was intense. We bumped into each other; playfully pushed each other around; he rested his hand on my back; he got so close to my face, I was certain he was going to kiss me.

The intensity of my feelings for him has only increased the more I get to know him.

But here’s where I need to be realistic and stop kidding myself.

  1. The commitment that I made to myself one month and one day ago is still important to me. Yes, I’ve slipped up. But I haven’t had sex (or anything close to it). I haven’t put myself in a position where I feel guilt or shame in over one month.
  2. If Samuel really wanted to be with me, I don’t believe that many things would get in the way of that. He hasn’t made any overtures to express that he wants a relationship. I feel like I’m a good friend that he occasionally sleeps with. Nothing more.
  3. I believe my feelings for him will pass eventually. Sure, many people would say that if I didn’t spend time with him it would probably be a lot easier. And they are probably right. But I also know that friends aren’t exactly falling off trees at the moment. Genuinely I do enjoy his friendship, and it has been important to me over the past month.
  4. Since November 14th, my feelings about my value and worth have increased. I judged myself so harshly for sleeping with four men in total. In reality, there are women (and men) who have slept with many more men than I have. Not only that, there are people that kill and steal and cheat. I am NO saint, but I need to be a bit easier on myself.

So that’s where I am right now. I realize this is long and rambling, but it helps to get it off my chest.

Four Weeks + Jake

These past four weeks have flown by.

While I know I’m still not ready to pursue dating, I do feel that even in the past month, I’ve learned a lot about myself.

I’ve also had the opportunity to distance myself from Jake, one of the men that I had been seeing for about 6 months after Glen.

I haven’t talked much about Jake on the blog yet. It’s not because I don’t want to talk about him; it’s more that I have SO much to say that I don’t even know where to start.

One of the reasons I began my “guyatus” was because of Jake. Our relationship was really only physical, and I knew that I deserved more. Sure Jake was nice, but he had absolutely no desire to pursue anything other than a sexual relationship. He also has a drinking problem (which he won’t admit). So basically he’s a pretty poisonous person for a recovering binge eater.

We met about three weeks after Glen and I broke up. I thought I was ready to date again. I wasn’t. Long story short, I drank way too much and had sex with him on the first night.

My heart felt so vacant after Glen, so I was just trying to fill a void. And to be perfectly honest, I never really liked him that much. I didn’t think we were at the same level intellectually, we had completely different goals, and our conversation was minimal. He was cute and a warm body, so I let the other (BIG) things slide.

After several months of this, I realized that being with Jake was only hurting me. In the beginning of November we got into a vicious fight and stopped talking. Looking back, that fight was a fortuitous turning point. It allowed me to see Jake in a way that I had never seen him before. He seemed smaller emotionally, less attractive, more insecure.

It became clear to me that a relationship with him would never work.

So here I am, four weeks out. Sure I’m still feeling lonely, but at the same time I feel immensely more secure.