The dreaded Zone

I'm in a bit of a predicament. It's about this guy. (It always is, isn't it?) I've known him for about two years now. We've bumped into each other at various professional events, chit chatted and nothing more. I never really thought much of him other than an easy-going, funny guy. In the last few months, I started to get the feeling he might be interested in me. I hung out with him in a group once and my girlfriend who was there confirmed she thought he liked me. Later that week he emailed me and asked me to hang out. Just us.

I wasn't interested in him in that way. He was fun to chat with, but he's not...shall we say...traditionally handsome. One of my girlfriends rated him, on a scale of 1 to 10 with 1 being butt ugly, 5 being average and 10 being perfect, a "2." Another girlfriend bluntly said he didn't even make the scale. So, needless to say, he ain't Brad Pitt.

Anyhow, I had to make it clear to him he was in the Friends Zone, that dreaded category of guys who are really sweet and sensitive but whom the girl will never sleep with. So when he asked me to hang out after work, I suggested lunch instead. When he called me later and left a voicemail saying he just wanted to see how I was doing, I never returned his call. YES it was rude but I believed it was necessary to demarcate the boundaries of the Zone. Afterwards, I never affirmatively contacted him; it was always he contacting me.

So that was that. Friends Zone boundaries have been clearly marked. Everything is hunky dory now, right?

Right?

Last Thursday, he emailed me asking me to go to an outdoor art fair on Sunday. I had plans with a girlfriend Sunday evening, so I replied that I'd run it by my friend and maybe we'd stop by (again, reiterating the Friends Zone by bringing along a friend).

Later that same day, I was having an after work drink with my girlfriend (the one who said the guy didn't even make the scale), and we were talking about boys. As I sipped my vodka cranberry, I began to muse over the various guys I've met and dated this past year. Then I thought about the Friends Zone guy. "You know," I said, "if he were just a little bit cuter, I might actually like him. You know?"

She looked at me warily. "Uh huh..." she nodded slowly while stirring her drink with her black stirrer.

I took another sip and thought about it more. "I mean, he's funny, smart, laid-back," I added. "He's pretty cool."

She continued to look at me warily. "I think," I said hesitantly, "I think...on some level...I...actually...might--" her head strained forward at this point "--you know. On some level."

She put her glass down. "Wow," she said, staring at me. "For you to overlook completely someone's physical appearance and like someone solely based on personality -- that shows what a good person you are." She lifted her glass again. "Wow," she repeated.

I couldn't help but laugh. It was supposed to be a compliment, but it showed how hideous she thought this guy was.

Afterwards, as I sat on the train home, I thought about him. And then it hit me. (Like a train, no less.) Maybe I did like him. What was holding me back? There was nothing wrong with him. In fact, I always felt really comfortable around him, good, even. And he made me laugh.

No no no no, I thought to myself, it's the vodka talking. You'll wake up and this'll be just a drunk thought.

When I woke up the next morning, the first thought I had was of him. Not just a thought, but a dreamy giddy happy thought. Crap! I thought to myself, I do f-ing like him! What now?!This never happened to me, a guy friend "growing" on me. Well, okay once. My last boyfriend.

I went to work, still startled by my recent epiphany. My girlfriend emailed me saying she would pass on the art exhibit "but have fun!" So I emailed the guy and said I'd go.

Sunday arrived. And it came time to decide what I was going to wear. T shirt and jeans? Tank top and capris? Or cute strapless summer dress that brushed against my thighs? Hmm. I realized I must have liked him because I went with choice C.

We met at the art fair entrance and he came armed with a couple of small bottles of red wine. "BYOB," he said to me as he tapped the cloth bag holding the Cabernet. "Cool," I said. How did he know I liked red wine better than white wine?

We walked amongst the paintings, sketches, abstract sculptures and jewelry, musing over whether or not we could replicate the art ourselves.

"I could totally do that," he said to a pile of dirt on the floor. He looked at the price tag. "And for $900 a pile, that ain't too bad."

"But you don't get it," I said. "The 'latent earth' is arranged in a certain way. There's an energy to its randomness."

He looked at me. "Yellow Gal, it's a pile of dirt on the floor."

I laughed. "You have no vision," I insisted.

"Dirt is dirt. Now that is art," he said pointing to a Monet-esque landscape.

"Fine," I relented.

We walked for a bit more and then sat down at a park bench to sip on our little wine bottles. He pulled out a container of Cheez-It crackers. "Instead of cheese and crackers, I brought cheese crackers," he explained with a nod. I couldn't help but laugh.

"Drinking wine from a bottle on a bench, very classy," I said as I unscrewed the cap of my wine bottle.

"Yeah, the only things we need are some newspapers and a shopping cart full of garbage bags."

"Mocking the poor, I like it," I nodded. "Cheers," I said, holding up my bottle. "Cheers," he responded, and we clinked our bottles.

I had an amazing time with him. We cracked each other up over the most random stuff. And I discovered we had a few more things in common. I felt so much more attracted to him. Crap, I thought to myself, now I really really like him.

As the day waned and the artists began packing up their exhibits, he turned to me and asked, "Are you hungry? I could go for some Yellow food."

I gasped. Not only did he know my preference for red wine over white, but he also tapped into my ultimate weakness: Yellow food. My own comfort food. And while he wasn't exactly my shade of Yellow, I knew he wasn't just fronting like he liked it, because he started rattling off specific dishes that only a true fan of the cuisine could know. I was impressed. And even more enamored.

"I so wish I could, but I'm meeting up with my girlfriend for dinner," I said, truly disappointed.

"Well," he said, "I'm going to Yellow Town anyway."

"But she lives right around there, maybe I'll go with you for a bit before I meet her?"

"Oh-kay," he said. Yes, I was making it pretty obvious that I wanted to hang out with him more.

So we took the train to Yellow Town and as we walked towards our particular restaurant destination, we saw a long line.

"Argh, there's a line." I looked at my watch. "I have to meet her in an hour, so I guess I'll just start walking to her place."

"Okay," he said. Then he walked alongside me in that direction.

"Oh, are you walking me?" I asked. "It's a bit away."

"Only until I see another place for food."

He ended up walking me to her place. Two miles. He stopped at her apartment lobby and looked at me. "This was cool," he said.

"Yeah," I said smiling stupidly. I had no idea what the F to do. I suddenly felt like a moron.

"Okay, see ya," he waved.

"Oh, okay, bye," I responded and waved.

And that was that.

Now I feel totally clueless. If this were purely a dating situation, I'd wait to hear from him. But I had previously demarcated the Friends Zone. How to un-demarcate short of wearing a sign that says "Do me"? What if he's lost interest? My friends defined the art fair outing as a date. It certainly felt like one. But was it?

It's so funny. Before when I talked to him, I was so lackadaisical. And now that I actually like him, I'm completely anxious, and I'm scouring my flimsy repertoire of dating knowledge to figure out what to do next.

Why did it take me this long to realize that I liked him? Did I like him all along or did it just hit me when I put it together that one night?

Who knows. I just hope I didn't F this one up.