The Fairytale and the Friendzone


Okay, so as per my promise to myself, I decided Sunday would be the day. That was the day that I would ask Hot Bartender to go to a wedding with me. I spent all week preparing for this … and freaking myself out mostly. What can I say? I couldn’t help it!

Some more backstory on why I thought this was a good idea when my friends attempted to dissuade me. Basically, with a few exceptions, many thought he would turn me down and didn’t want me to be disappointed. Now, I know they did this out of the goodness of their hearts, but I would have liked for a  majority vote of “Go for it!”

I guess I was the main person driving me for once. The reason for thinking there was even a one percent chance he would say yes? It was surprising to think about it altogether, but really, we are good friends. We have funny inside jokes … bits we always do together … small moments that just make me smile. Like when I was doing a birthday announcement in the restaurant and I looked across the room and he was leaning against the pop machine negligently, watching me and motioned his hand higher pretending he couldn’t hear me. I laughed, breaking the announcement slightly and then he gave me the thumbs up, happy he’d succeeded in distracting me. Devilish moments, but some of my favorites …

So I knew I had to ask him. This has been in the back of my mind since New Years, but if you haven’t been able to tell, lately I’ve been doing some brash, bold things. Totally unlike me.


The morning before my shift, I did my hair and makeup while watching episode after episode of MTV’s Friendzone. It was really very motivating! I love that show. The rejections balanced out the accepted dates and it kept me balanced. I waited for the opportune moment, He was alone behind the bar, no customers and I walked up, and leaned on the counter and while my heart stopped, I got it out.

“So … I’ve got a proposition for you.” He quirked an eyebrow and asked what it was.

I told him how my old telemarketing boss was getting married and though it would be a fun time with a lot of alcohol (I really tried to hype this part up), that I wouldn’t know anyone there, and that I KNEW he really wanted to go as my Plus One with me.

He finished uncorking the wine bottle and asked when it was. After I told him, he said, “Sure, that sounds good. I should be able to do that.”

I wasn’t quite sure I had heard him. This was one of these things where you want to hear it so much, you’re really afraid that you just imposed the answer you wanted to hear and they actually said sorry I can’t.

So in the interest of not sounding crazy (and possibly then sounding crazy….) I asked him if he was sure and he responded in the affirmative yet again. This time I knew it was no illusion. So I told him I’d put us off in the book if he was sure (and unfortunately I realize this was me, double checking again because I simply could not believe it) and he smiled.

“Yeah, put me down, I’ll go.”

Those words, while they weren’t declarations of love, were a doorway to my shot. I know I’ve purposely put myself in the friendzone with him. But we need that boost to get out of it. I feel like the wedding’s my shot. My one chance to show him how good we could be together. It’s my interview and I don’t want to blow it …

I didn’t tell him that it was a two hour drive. He didn’t ask and I didn’t offer. It’ll be a surprise (I keep telling myself with a cringe). But honestly, I didn’t want to push my luck too far!

So I put us down in the book, bribing my manager with my best pen to solidify our time off. It was worth it.

Before leaving, I caught Hot Bartender and told him that I had put us down in the books and that he needed to let me know in plenty of time if he couldn’t make it so I would have a lot of time to plan some great revenge. Really painful, I assured him. He thought it was hysterical and kept laughing even as I left the restaurant. He always jokes that he’s afraid of my revenges … they always are creative and devious 🙂

Now I just have to wait until Memorial Day. I’m on the countdown and hopefully it all goes as planned because I have some really great plans…

I’m so happy it’s almost debilitating. The fantasies really need to get under control. But really, I just can’t believe it—he said yes! This isn’t a Cinderella story, but I feel like I can go looking for some really awesome shoes–hopefully I won’t have to lose one so I can see him after the wedding!


Christian Louboutin is the obvious choice for my impossible dream shoes 🙂


2 thoughts on “The Fairytale and the Friendzone

  1. Go girl! Get that hot bartender!

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