July 3, 2012

most. awkward. email. ever.

Posted in dating, Relationships tagged , , , , , , , , , , , , , , , , at 1:20 am by singlyoutrageous

As I relayed in my most awkward post yet back in April I have some issues with sex. D and I have had some conversations about this, but I find it extremely difficult to talk about. Since I was having so much trouble articulating my feelings on the subject, I did what I always do when I am struggling with something on my mind- I wrote about it.

I wrote about my sexual hang-ups in a very analytical way so as to see if there were also some possible solutions. I wrote about my low self-esteem, poor body image, lack of experience due to where my life led me and more. After I re-read what I wrote, I realized I have some fairly serious issues. Not only did I write about my issues, in embarrassing detail, I then emailed said writing to D.


Most awkward email ever.

I had copied my text into an email, taken a deep breath and hit “send”. I have no idea what came over me. This was way personal stuff. Like digging deep on the therapy couch stuff. Some of which I had just realized about myself while writing it. And I sent it. To him.

I had sent him a warning text so that he knew what to expect. After reading this mortifying information about myself, he sent me a text back. His response was:

“I feel honored that you shared your deepest feelings with me. Thank you. I’m not sure if I can respond any other way than to say I appreciate the courage it took to send that to me.”

*sigh of relief*

I replied that the only response I was worried about was scaring him away. He said he’s not going anywhere.

I feel better now that he knows where I’m coming from.  I just hope things aren’t off the next time I see him. I’m not sure what to expect.

April 23, 2012

Did I really just ask him that?

Posted in dating, Relationships, running tagged , , , , , , , , , , , at 3:07 am by singlyoutrageous

How do you ask someone an objective or hypothetical question as an actual objective or hypothetical question, and not as a question that leads to a conversation related to yourself? I have a friend who asked her guy friend if she was dateable. She did not want to date him, but truly valued his opinion and was interested to know it. So he leads with “Well, I wouldn’t date you, but here’s why…” She got his opinion, but in a way that was insulting to her.

So I get the bright idea to ask D if he’s ever been in love. It is a subject I was purely curious about, because he has not been in any serious, long-term committed relationships. To my detriment, I asked him while we were drunk, and probably didn’t get my point across properly.

I led with “I have a question to ask you, but don’t want you to think it has in any way to do with us, it’s just something I’m curious about.” Or so I think- like I said, I was drunk, so this is just a slightly inaccurate reenactment of how the actual conversation went. D’s answer was essentially “no”. I don’t remember if he said “no” before or after he said something like “Well, when it comes to you and me…” What a mess. I also don’t remember if I asked the initial question before or after we stared intensely into each other’s eyes while listening to Boyz II Men. No, I am not joking! It was very romantic. Anyways, I don’t remember the context in which I asked the question but it was obviously taken in the way I didn’t want it to be taken. I followed up with a hasty, “Well I have loved people, but have never been in love with someone,” and “I also feel there’s a difference between love and infatuation.” He ended the conversation on a good note, saying he appreciated that we could discuss such subjects in an analytical manner. Hmm. Whether or not he believed me when I said I didn’t want to know if he loved me, I don’t know.

I am currently training for my second 5K that is happening this Saturday, so there will be no drinking for me this week. This means no drunken conversation starters that sound like  good ideas in my head, but then not so much when they come out of my mouth. We’ll see if I’m any less awkward when sober. I have a feeling that won’t be the case. 😉


April 5, 2012

A nice night in…

Posted in dating, Relationships, running, therapy tagged , , , , , , , , at 8:14 pm by singlyoutrageous

I went over to D’s place last night. And nothing happened. Well, I shouldn’t say “nothing happened” but I did not sleep with him.

We had a nice relaxing night, quite different than our norm of going out and drinking. We grabbed something to eat, then went back to his place where we ate and chatted. We watched a little TV and cuddled. We each had a glass of wine, and enjoyed each other’s company. It was just really nice.

My therapist told me today that I am doing so many things right, that she needed a pen and paper to write them all down. I graduated to spacing our sessions out a little more, and left her office feeling pretty good about myself. She did give me a few good things to think about and reminded me repeatedly to not get so far ahead with this relationship in my head, and just take it nice and slow. Also, that I should work on other relationships in my life just as much as this one (family, friends, etc.), because they are all equally important.

I am definitely in uncharted territory, and am doing my best to stay on track.

On a final note, I am running my first 5K in two days. I am feeling pretty confident about it, and very proud that I am achieving a goal I set for myself.

March 20, 2012

A good day…

Posted in dating, Relationships tagged , , , , , , , , , , at 1:59 am by singlyoutrageous

I had a very productive and rewarding day today. Physically, financially and emotionally.

I ran for the first time in 2 weeks since injuring my knee. I was careful not to push myself, taking it slower than I would like to because I do not want to get hurt again. (Yes, @kelli, there are similarities between my relationship style and my running!)

I also straightened out my monthly budget. In the past I have created many budgets with nothing but good intentions, and simply never followed through with my spending. I have every intention of following this budget now. It will bring me one step closer to my financial goals.

Also, D and I had a very entertaining chat via text message tonight. During our last date I had suggested that we watch a movie at his place when we go out on Wednesday. Afterwards I thought about it, and decided that a movie at his place is probably moving too fast for me. I don’t feel like this is moving too fast, but logically I know that it is. I want my therapist to see that I can follow her advice at taking things slowly when I go to see her on Thursday.

Anyways, while D and I were texting earlier, I told him we should postpone our movie date and go out for a drink or coffee instead, due to the fact that I am an opportunist, and wouldn’t want to place myself in a situation where I may take advantage of a man with high moral standards. He was cool with that. He seems to be pretty cool in general. I keep waiting for the punch line. A guy that is smart, good looking and funny likes me? What’s the catch?

February 24, 2012

Too much impulsivity and an awkward domain name…

Posted in dating, Relationships tagged , , , , , , at 12:07 am by singlyoutrageous

It was a pretty good day. I persevered with my new running routine, and even ran in thirty-something degree weather in the rain. And there’s more- I asked another guy out.

The only bad part of my day is that I haven’t heard from R in a few days. This wouldn’t normally bother me, but R had built up certain expectations for himself by texting me on a daily basis for weeks at a time. So two days have gone by. I am a little disappointed, but handling it well.

To help me avoid thinking about R all night, I bit the bullet and texted A. I said that I knew he’d been busy at work, but wondered if he wanted to grab drinks or dinner sometime? He texted me back surprisingly quickly, saying he would love to and was I available this weekend? We have tentative plans for Sunday night. I am thrilled. Not sarcastically so, but actually so. I know now that second dates can be just as awkward as first ones, but I also know now that it gets better. I feel slightly more experienced having gone out with R so many times in the past month- and definitely more confident.

As my friends continue to remind me, it will do me good to see who else is out there. I have always had a bad habit of being impulsive when it comes to major life decisions, such as buying a home. I have purchased two homes, both of which were the first I looked at, and both of which I eventually regretted purchasing. Another life decision I am too impulsive about would be dating a guy. The first night I met my ex-husband (at seventeen years old) I told a friend “I’m going to marry him someday”. This decision I also eventually regretted. I need to continually remind myself there are other options out there, and not just jump into bed (figuratively or literally) with the first guy I meet. Dating others will hopefully help to break me of this impulsive cycle.


A few words about my domain name “https://misadventuresofmyakwarddatinglife.wordpress.com/” I know, I know, I misspelled “awkward”. It was around 3 am when I decided that I would like to create a blog to vent my feelings on my awkward dating life. Also, spell check does not work when you are typing many words together into one long word for a domain name. My first post was quite lengthy and also took a huge weight off my chest. It felt great to get everything out there, and off of my mind. I slept better that night. I realized the spelling error I made the next day and was disappointed in myself, but decided not to change it. The incorrect spelling demonstrated my frame of mind at the time of my blog’s inception, so it seemed fitting to leave it, so please don’t judge me based on my shoddy spelling. 🙂