Help: I Might Go Crazy

Feeling especially refreshed yesterday morning, I woke up feeling great. The day prior, Monday, I went to yoga, got a much needed hair cut with my mom (summer had left a serious mark on my once-beautiful ends), and ended up running 4.5 miles at sunset.

I basically woke up feeling brand new... minus 3 inches of hair (less is more, right?), and plus extra sore legs. Rolling  out of bed (literally), I decided to get outside. Cozying up on some grass, I opened up the book I have been reading. 

The weekend before last, I purchased a trendy self-help book from Urban Outfitters by Susie Pearl, called Instructions for Happiness and Success. Up until this summer, I would have been ultra-embarrassed if someone ever saw me with such a thing, but it is a great book. I decided to work on a chapter, and felt even better than how I did when I woke up. I honestly recommend this book to everyone—she has incredible points to make about attracting even more happiness to your life. 

Once I finished reading/writing, my mom and I had our eyebrows done. This was only the second time that I have had them waxed—resistance to my mom was very effective for years—so it hurt incredibly. I was crying within seconds of her first rip. This woman was paid to make me cry. Not cool.

As I was laying there, she told me that she wished "this one would go up more." Great, now my right eyebrow looks uneven. My mom reassured me, "They look great sweetie!" Even if they don't, at least they grow back, right?

In the afternoon, my mom needed help with an event, so I looked extra nice. Studying my face and head with concern a few hours prior, she asked me, "You're going to do something with your hair, yeah?" Obviously. (Cue eye roll.) 

Kevin and I were, hopefully, going to hangout after as well, so I put on an especially pretty pair of underwear and spent extra time making sure my legs and flower were perfectly smooth. I'm talking "smooth-like-butta" smooth... I'm talking, "smooth-like-Ryan Gosling, professing his undying love for me, after realizing I never opened the beautiful letters he penned me" smooth. (I'm still waiting on that by the way.)

We had planned on me texting Kevin once I was done assisting my mom, so I sent him (what I think was) a funny picture of Spongebob asking Squidward, "Are you finished with those errands?". After a while of random conversation, I began to wonder when he was going to tell me whether he could or couldn't hang out. Well, that never came, so I kind of sat around waiting for the better part of my evening. 

I am trying not to care too much, because I have no clue what is going to happen, or what he even thinks of me. Obviously, my efforts have not been that great because my emotions sway as much as a ship struggling on a fully-developed sea. He understands that I leave on Saturday, having commented, "nicee, a few extra days :)." Since we parted on Thursday night last week, I have been so excited to see him again. Between honest enjoyment of his company, and a re-inspired desire to get some, I have been looking forward to combing my fingers through his short, dark hair and to pressing myself against his shirtless body. Basically, I zone out regularly, drifting into great sexual daydreams. Figuring that he felt just as fervent, I, wrongfully, assumed that I would have seen him by now.

In the dark on his thoughts, I don't really know what to expect in regards to the talk we are going to have before I leave. I'm extremely annoyed with piecing together his little hints because they give me tons of room to misread our situation. I know that he thinks it would have been "meager" to have a two-and-done. With such an obvious reference to sex, does that mean that he is only focused on getting some? I made it pretty clear that sex is kind of important to me, so do you think that he would so blatantly take advantage of me? 

If I were allowed to read such a thing, I feel like this would be a page ripped right out of the player handbook. I feel like someone convinced me that I would be able to hop a fence, only to get caught at the top, straddling something that was ready to destroy my lady parts. But, then again, he seems too kind (and clueless) to fuck me over like that. 

When I originally told my best friend, Bailey, that I was hanging out with Kevin, she characterized him as being a little "derp," which is how I affirmed my slight intuition of him being a bit clueless. Unfortunately, our conversations are totally all over the place since Bailey and I have to communicate cross-country (she goes to school in Boston), so I never found out exactly what she meant by that comment. 

Hoping that she would be asleep (I was right) so that she could mull it over on Monday morning, I texted her before I cashed in on Sunday night. Word-vomiting, I sent, "Kevin and I slept together already. Game changer, I know. NEVER STOP LOVING ME BAILEY."

I understand that she doesn't judge me (too much), but this would so not be in her comfort zone, especially because she is fairly conservative/religious. Waking up to her excited demand for details, I wrote her nothing less than a novel.

"Yeah its been a long ass time for you and I really respect you for holding out on sex because most people I know who have already done it basically do it all the time."

"Thanks. At this point, I'm glad that I did it. Holy shit, I have been missing out Bails." We always joked about how long my streak would last, laughing at how long I hadn't gotten my freak on. 

"I mean, as long as you don't regret it, I support you. Also, low-key jealous that you were able to do the deed on the MB golf course. Like that's some serious summer fling stuff right there."

The thing I love about Bailey is that regardless of our different views, she always makes it a point to support me regardless of the decisions I make (normally they aren't too bad). Although we are forced to catch up over the phone these days, I still regard her as one of my absolute best friends, and treasure her advice and support. 

Expressing my vulnerability, I admitted, "I'm interested and nervous to see how things play out."

She responded, "I think it's a good idea to tell Kevin how you feel since you guys seem pretty comfortable with doing that."

So here I am, still unsure of what to do. Should I initiate a conversation with Kevin about what's going to happen with us? Or should I wait for him to bring it up? So far, I haven't been very confrontational about my feelings (except for the time I told him I didn't know if I wanted to have sex). But, at this point I might go crazy if I have to keep guessing about what he thinks of me until Friday.