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 17, 2012

My most awkward post yet…

Posted in dating, Relationships, therapy tagged , , , , , , , , , , , , at 2:20 am by singlyoutrageous

Thank you, New Single Guy, for nominating me for the versatile blogger award! It made my week. 🙂 I will be writing my post in response to my nomination tomorrow, so stay tuned…

The following post was difficult for me to write. Difficult and awkward. It is about sexuality which is an uncomfortable subject for me, so I apologize in advance if it is a bit of a mess!


prude [pruːd]


a person who affects or shows an excessively modest, prim, or proper attitude, esp regarding sex

[from French, from prudefemme, from Old French prode femme respectable woman; see proud]

prudish  adj

prudishly  adv

prudishness , prudery n

Collins English Dictionary – Complete and Unabridged © HarperCollins Publishers 1991, 1994, 1998, 2000, 2003


Yes, I think that this describes me. It’s not that I want to be a prude, but my past experiences, or lack thereof, have led me to this point! Part of my problem may be that I was with the same person (my ex-husband) for so long (about 13 years) that I never learned as much about sex as those who were able to date around during their 20’s. My ex and I had the same kind of sex after being together for 10 years that we had in high school, and high school sex is not great. For me, high school sex consisted of the following: lights off, eyes closed, no kissing and no orgasm.

My girlfriends have always laughed at me when they would try to talk about sexual experiences because the reaction I would provide them with- I was mostly embarrassed, generally uncomfortable and definitely awkward. I wonder now if the way I react to sexual banter and sex itself is simply because I feel I have a lack of knowledge and/or experience. I don’t know. Even after my divorce my first sexual encounter was anxiety inducing and slightly uncomfortable. I had a great time, but my mind was going in a thousand different directions at once. I also felt I needed the aid of alcohol to enjoy myself, which is never a good thing. I told my therapist when I first started dating again that I had a huge fear of intimacy. She assured me that when the time came, it would (hopefully) be with someone I cared about, and that fear would be irrelevant. I’m working on it.

The real reason I started writing this post is due to some particularly saucy texts I received from D last night while at work. When does texting become sexting? I’m not talking about racy photos, just racy comments. I think that whether or not a particular text is a sext is objective and varies person to person. I was definitely blushing and also turned on, so I think I can label D’s texts as sexts.

I, however, lack the confidence to respond in a like manner due to my “prudishness”.

How do I improve my confidence in bed? How do I overcome my prudishness and reply in kind to a sext? These are things I want to do, but don’t know how (though I think writing about them in a public manner may be a start!).

Here is an excerpt from the conversation I was engaged in earlier with D:

As our texts were getting more and more “interesting” I texted that he had better stop, because I was blushing and didn’t want to explain why I was blushing as such to my coworkers. His responding text (I think sext at this point) went something like this: “That’s too bad. I guess I won’t mention anything about licking certain body parts of yours (below the waist), kissing your neck or holding you close and whispering how much I want you. Nope, not going to mention that.”

OMG. Really. What do I do with that?! Is there a class I can take somewhere on how to be a great lay, and how to sext with your boyfriend? Please direct me to it!

After writing this I have come to a realization. The beautiful thing about the relationship I have with D is that I feel like we can talk to each other about anything. I may not have bared my soul as much as he has yet, but maybe it’s time. I think that this will be a great conversation to have with him on our next date.

Thanks as always, for listening.

April 10, 2012

I have a boyfriend- I think.

Posted in dating, Relationships, running tagged , , , , , , , , , , at 1:37 am by singlyoutrageous

I completed my first 5K run on Saturday morning. A lot of elderly people and small children may have passed me (both awkward for me), but I ran the entire time and that was my ultimate goal. My time was 36:25, which I feel is pretty respectable for a first time 5K’er. It was a lot of fun, and really fulfilling to meet a goal I had set for myself. It was especially fulfilling since this goal stemmed from my first awkward relationship post-divorce. I had been so consumed with my relationship with R that I had to think of a distraction from him, and running was it. The beautiful thing is that I don’t think about him all the time anymore, and didn’t think of him once on race day, even though he was one of the main reasons I was there.

I signed up for my next 5K as soon as I got home.


The next night D took me out to dinner and for a few drinks. I filled him in a little more on my history with my ex-husband, but only because he asked. I felt like I may have divulged a little too much information, but he just thanked me for being so honest.

Later, over drinks, I could tell that something was up, and asked D what was on his mind. He replied that he wanted to say something, but didn’t know if he should. I of course encouraged him to do so because there is nothing that irks me more than someone who says they are going to tell you something, then changes their mind and won’t. Anyways, he finally does tell me. He tells me that he doesn’t want to see anybody else- only me. I told him that I absolutely felt the same way. He wasn’t sure if he should have told me this, because he was worried it was too much. I assured him it was definitely not too much.

Now, I thought we were already sort of “there” since I knew from the beginning that I was the only girl D was dating, and we had a mutual agreement not to date around on each other. So this must mean something more. Like a declaration. Like we’re boyfriend and girlfriend.  Right? The best part is (and I cannot believe I am typing this, but I am) is that we still haven’t slept together. I know this is how relationships are traditionally supposed to progress, but I have never been a traditional kind of person. But it’s a welcome change of pace. Plus, it just gives me one more thing to look forward to.

April 6, 2012

A very awkward encounter…

Posted in dating, Relationships, running tagged , , , , , , , , , , , at 11:35 pm by singlyoutrageous

I am hours away from my first 5k, but I absolutely had to get this story out of my mind and on to my computer before I can get some quality sleep.

My plan for today was to grab lunch with an old friend, go out to dinner with my parents, sister and daughter, then meet up with D later that night after I grabbed my bib number for the race.

I had a great lunch; it was really nice to catch up with a friend that I hadn’t seen in such a long time. I had let our friendship slide to the wayside as my relationship with my ex-husband developed years ago, so it was definitely nice to reconnect.

Later, my dad decides he wants to go to his favorite pizza place for dinner. That was fine with me- I was going to grab dinner, run home, change then head over to D’s. Dinner was very nice- Little (my daughter) was really digging the fettuccine alfredo, and I was also loading up on some carbs for my race tomorrow. As we’re finishing up eating my mom classically says “Look who just walked in- no, don’t turn around!” First of all, I hate it when people do that. You tell me to look, I’m going to look. So don’t change your mind mid-sentence. Second of all, it was D’s parents.

D has a weekly dinner date set with his parents. He lives about half an hour away, so this is a weekly opportunity for him to see his family. But really, is our town that small? I didn’t think it was, but I have obviously been proven wrong.

A few minutes later and D walks in. We are situated in such a way, that without blatantly turning around, I could not see where D and his parents were sitting. He, on the other hand, had an excellent view of the back of my head, my sister’s head (whom he has met) and my parents. I was freaking out a bit. I wasn’t prepared for a situation like this. A few minutes of fidgeting nervously with the baby and packing her up, then it was time to leave. Time to walk almost directly by their booth. I could have bolted for it. I could have looked the other way and ran. But that would just be rude. I turn towards where they are sitting and wave at D. He waves back. Not in a welcoming, “come on over” way, but in an “I can’t believe this is happening” way.

So I throw Little on my hip and march over to where they are sitting. “So you’re following me to dinner now?” Is what D says.  I say, “Hi, I’m Kim, this is Little.” D’s dad immediately reaches across D and starts tickling the baby. His mom says, “Hi! I’m D’s mom, and this is his dad…” D replies that they have names, and supplies them. His mom goes on to ask me who my dad is, because she knows that one of her good friends is an aunt of mine. My sister wanders over and I introduce her. Then my dad wanders over and shakes D’s hand, and chats with his mother for a few seconds. My mom is paying the bill, so doesn’t get to join in the fun. “Well, it was nice meeting you,” I say to D’s parents, then to him “I’ll see you a little later”.

After we leave I am mortified at how D acted. He seemed really uncomfortable, and as if he wished he weren’t there at all.

A little while later D texts me (sarcastically I assumed) “A stalker who brings the family along? You are different.” So I’m thinking now-okay, maybe I’m overanalyzing the situation, he seems okay.

Once at his place we talked about the dinner fiasco immediately. D actually started with “Thanks for being the adult tonight and coming over to say “Hi”, because I couldn’t”. I told him how I felt he was acting, and he told me what was actually going on. He simply wasn’t prepared for the situation. It caught him off-guard, and he didn’t know how to react. He went on to tell me that my daughter was pretty adorable, and that his mom thought I was pretty.

So my theory is that his social anxiety may have had a part in how he acted at the restaurant, but most of all I feel that he needs to feel some control over a situation. Not that he’s a controlling person, but that something unexpected happens and he doesn’t have control, he doesn’t know how to act. I know he has some issues like this, and time will only tell how I react to them. But we all have our issues, even me.

We spent a nice few hours watching TV, talking and cuddling. No sex occurred. This was the second time for me to be at his apartment and not have sex with him. It’s pretty great. I think I almost felt like if we were alone at his place sex was a decided factor. It’s not, and I’m happy about that. It is different and pleasant to be taking things at this pace. It’s nice to know that we will have sex eventually, but I am not feeling pressured to do so in the meantime. It’s kind of weird- but in a good way.

So, I don’t think a  more awkward meeting of our families could have ever been planned, and I actually feel relieved that it’s over and done with. It was a beneficially awkward night, for sure.

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.

February 25, 2012

Help- please!

Posted in dating, Relationships tagged , , , , , at 10:58 pm by singlyoutrageous

I just got the overwhelming desire to call R and tell him it’s okay if we have sex because I’m dating other people too. How does that even make sense? How did I become so needy? What I would like from a relationship with R is to see where things could go, and possibly have some real commitment. I don’t want casual sex. So why am I so tempted to call him and tell him that’s essentially what I want? Is my self-esteem that low, or am I just tired of not having completely awesome sex? My emotions are ruling over my head right now, and it’s not good.

I’m not calling him tonight, but somebody needs to knock some sense into me. Or give me some advice- I don’t have another appointment with my therapist for almost two weeks-please help!