The Dateable Dork

OMG, dudes, what a disaster!  I mean, it wasn’t completely a disaster, but I am seriously such a dork, and who knows what he hell he must think of me.  Ahhhhh!!!!  Really, I shouldn’t be allowed to date anyone.  They should just revoke my dating license and throw me in solitary confinement for the remainder of my ridiculous existence.  Ahhhh, what a dork, I swear.

Here’s how it went down:

I wanted to get together with this guy that I’ve been seeing – who shall henceforth be known as Chicago Boy – at some point during the weekend, but turns out that the only time we were both going to be in town was Friday night (last night).  He was free, but I already had plans to do dinner/dancing for a friend’s birthday that night.  We went back and forth trying to find an alternate time to meet up, but it just wasn’t working out.  Sooooo, I decided to invite him along for the after-dinner birthday festivities with a handful of my friends.  Good idea?  Bad idea?  It was too late to really think about it because by the time it hit me that our third date was going to be with a bunch of my friends, I had already invited him along and it was too late to back out.  So, I went with it. 

After dinner, my friends and I met up with Chicago Boy at a bar, and we all hung out for a few hours drinking beers, chatting, etc.  To my surprise (and relief), my friends seemed to approve, and he really held his own during the conversation.  Thank god!  I was bracing myself for disaster, but this part of the night actually worked out really well.  I even felt comfortable enough to run to the bathroom at the bar, leaving Chicago Boy to fend for himself with my friends for a few minutes.  He even bought us all a round of drinks.  Excellent!

The bar scene was kind of dead last night (at least at the few bars that we went to), perhaps because last weekend was St. Patrick’s Day, and maybe this weekend everyone was just taking a break or something.  Whatever.  It was kind of a bust in the dancing department, so we all decided to part ways for the night and head home.  I said goodnight to my friends, which left me and Chicago Boy to our own devices.  We decided to head elsewhere for one more beer, and we wound up in a very cute little bar that I don’t go to often enough.  Must add this to my list of regular hangouts.  We chatted there until about 1:30 or so, and the conversation and flirting and all that good stuff was going pretty well.  Again, thank god this part of the night was going well because little did I know what I was in for later on…

After we leave the bar, he invites me back to his place, and of course I am more than happy to oblige.  I say something like, “Ooooh, I get to see the bachelor pad!” through my drunken haze.  Real classy, DD.  Nice one.  At this point it was 100% obvious to the both of us that we were headed upstairs to hook up, and once we got into his apartment, we just headed straight for the bed and got going.  I walk into his bedroom and am surprised to see what I think is the biggest bed I have ever seen in my life.  Dudes, this thing was GIGANTIC.  He said it’s 8 inches wider than a king-size bed, and seriously, I believe it.  You could probably fit five or six people comfortably in this thing.  Killer.  And what a nice playground for me and Chicago Boy to play in! 

We start making out and almost instantly his hands are in my pants and I am playing with the cock.  Clothes are flung in all directions, and before I know it we’re rolling around naked in his huge bed.  Now, my dears, here’s where the disaster begins.  First of all, although I think Chicago Boy is totally adorable and we’ve been getting along pretty well, the first time in bed with someone can be a little awkward, and this was the poster child of awkwardness.  What the fuck, right?  Wasn’t expecting that.  But here’s the real problem: remember how I had some gynecological-related drama a few months back and haven’t had sex since?  Ummm, yeah.  I was surprised and extremely embarrassed to learn that one cannot just go having sex full force after something like this, and, well, it just didn’t work.  Also: ouch.  This only added to the awkwardness.  So we didn’t have sex, but instead just fooled around for a while until we both kind of just crapped out from being tried, being drunk, and getting a little frustrated with the total awkwardness.  Ugh. 

As we’re basically collapsed/cuddled up and drifting off to sleep, I notice two things: (a) his bed is seriously the most comfortable bed I’ve ever had the pleasure of sleeping on in my entire life – it was unbelievable how amazingly comfy this thing was; and (b) that “ouch” I felt earlier was something that definitely needed to be investigated in the bathroom.  So I get up to run to the bathroom (also to get some mouthwash – I hate going to bed without brushing my teeth – eww!), and I realize that some damage has been done in some extremely hard to reach places.  Shit shit shit.  There wasn’t much I could do about it in the middle of the night, so I resign myself to just get some sleep and see a doctor first thing in the morning. 

And here’s where the disaster continues: I walk out of the bathroom into a dark hallway of an apartment that I’ve never been in before.  I am tired and still kind of tipsy and worried about whatever I had just done to myself in my lame attempt to have sex.  I guess I wasn’t really paying attention to where I was going because suddenly I walk right into this HUGE metal/slate hallway table and manage to create a massive gash on my thigh.  By this point I am cursing and screaming and really not doing well at all.  I make my way over to the bed and Chicago Boy is trying to decide if he should be worrying about me or laughing hysterically.  I think he was doing both.  I was so delusional and in so much pain that at one point I uttered the phrase, “I want my mommy.”  Again, nice one, DD!  Way to attract a man.  We proceed to laugh and laugh as I am doubled over in pain and trying to predict just how big of a bruise I’ll have in the morning.  He said he could already see it forming on my thigh, not 5 minutes after I crashed into the table.  Oh god, I am SUCH a dork, I swear.

So after all that drama, we finally stop laughing and fall asleep in the super-king-size, super-comfortable bachelor pad playground of a bed.  It was cute that we actually cuddled up all night, and it was nice to have that kind of close contact with another human being.  I had missed it, to be perfectly honest.  I fell asleep entangled in his arms and legs.  Aww. 

We woke up this morning in a fairly good mood, considering that I had basically maimed myself and we didn’t really get all that much sleep.  He had to be out of the apartment early, so I got dressed while he showered, I kissed him goodbye, and we both headed out.  And that was that.  Immediately after I got home, I hopped in the shower, surveyed the damage to both the girly bits and my poor thigh, and made my way over to the closest urgent care center I could find.  A few hours and several embarrassing conversations later, I was armed with antibiotics and instructions to make an appointment with my regular doctor when the office opens on Monday.  And the bruise on my thigh is getting bigger and uglier by the minute.  Sigh.

So that was that, my dears.  Am I a walking dating disaster or what???  I seriously don’t know whether to write off last night as somewhat of a success (Chicago Boy and I continued to get along well, and hanging out with my friends went well, and he seemed to stick by me even after the sexual fiasco) or a total disaster (I completely embarrassed myself in more ways than one and am probably out of commission for any further sexual activity for several weeks; I’m sure that will go over REALLY well).  Ahhhhhh.  I’ll tell ya, if this guy ever calls me again after what happened last night, he will win major brownie points for embracing an injured and completely uncoordinated mess.  If he doesn’t, well, I’m sure I’ll have the opportunity to embarrass myself in front of another eligible bachelor soon enough.

I swear, dating will surely be the end of me.

P.S. – Ouch ouch ouch.