Awesomely Awkward

I'm going to start a new feature on here called Awesomely Awkward in which I present you, the fine reader, with an awesomely awkward situation that I have recently encountered. It could be work related or personal or even something I saw on the news. But each situation will be so awkward and uncomfortable that it is, inherently awesome. So sit back, relax, and be prepared to squirm in your seat a little bit.

Besides wasting away my mid-twenties in Corporate America, I am also a singer-songwriter who performs in Cleveland area bars and music venues. My claim to fame is having played the mainstage at the House of Blues in Cleveland, but my more typical venues are local bars and taverns. By no means am I a big deal, but I do get recognized every once in a while by total strangers, which is pretty cool.

I started my fledgling music career in college by first playing bass in a band and then transitioning to my current solo status. While in college, I recorded a solo acoustic album of original material written for girls who didn't "like me that way, but thought I was a great guy." Sluts.

Anyway, I did manage to date a girl during that time who I'll call Bethany for the sake of anonymity. I never wrote Bethany a song or anything, but she was around when I was writing songs for other girls. Why she put up with this for the few months that we were together is beyond me, but it's all part of the set up, so just go with it.

I dated Bethany for 3 or 4 months, but still "saw her" after we broke up. I was 21 and she was 18 so our relationship consisted of me going out with friends to get drunk and then calling her up around 2:30 in the morning to see if she wanted to come over. It was a nice little arrangement at the time, but in retrospect was probably a pretty lousy thing for me to do. (I had to put in this last sentence for any girls that might be reading this so that I don't come off like a total creep. Whoops. Too late.)

After a few months of "seeing" each other, we finally pulled the proverbial feeding tube (worst. analogy. ever.) and would occasionally run into each other around town. By no means did we keep in touch or even attempt to. In my mind, that chapter of my life was closed.

Fast forward to Tuesday night...

I'm at home checking my MySpace account (yes, I'm 26 and I use MySpace. Shut up. A lot of people do.) and I see a message from Bethany. I was a little surprised since I hadn't thought of her all that much over the past 5 years, but I had heard through the grapevine that she had gotten engaged.

Now, what makes this little story the first installment of the Awesomely Awkward Series (TM) is that in addition to wanting to "catch up" she also asked me if I would play some songs for her at her wedding this spring.

(I wish I had the full e-mail to cut and paste, but I don't so I'll try and paraphrase.)

She mentioned that she was getting married this spring and that her and her fiance were talking about music and she thought it would be a good idea to have me, an ex-boyfriend, play at their wedding. She said that besides being taken care of financially, there was also something extra in it for me. (Honeymoon threesome? I wouldn't put it past her.) Bethany told me that she was always a big fan of my music and loved my voice and thought it would be perfect for her wedding. Apparently the fact that the two of us had been intimate together never crossed her mind or mattered to her. The fact that most of my songs are about the girls I can't get never crossed her mind either.

So that's the situation. Pretty awkward, huh? Pretty awesome too, huh? I'd say this is Awesomely Awkward.

I haven't written her back yet because honestly, I'm not sure if I would turn this down. First of all, I love weddings. Free food combined with an open bar is pretty spectacular. Plus, there's the chance that there are single women there who are feeling just lonely and desperate enough to talk to a guy like myself. Another plus side of going would be to write a song to the bride and groom about how I "got there first" just to ratchet up the level of awkwardness a few thousand degrees. The final upside of going would be to come back here and write about all of it.

Of course, I probably won't go because a.) it's in the Smoky Mountains of Tennessee; b.) seeing an ex get married would probably be more sad than awkward; and c.) I've got better things to do with my time.

But if I did go... How awesomely awkward would that be? Pretty.

I hope you enjoyed the first installment of the Awesomely Awkward Series (TM). Seeing as I encounter various levels of awkwardness on a near daily level, expect a ton more of these. I'm getting excited just thinking about the possibilities.

Have a good weekend. I'll try and keep up with this thing more often.