For the Love of Jack

The Brothers Winchester

As soon as we got settled in with lunch, I reached in my pockets for my phone. I have to call Gabriel, I thought. I was still confused if Dean had asked me out as a friendly gesture because he was genuinely trying to meet new people or if he was interested. As much as I had hoped for the latter, I wasn't sure if I could handle romantic interest to anyone now. I mean I had so much going on with Jack and my job and adulting. There was no way I could date right now, right?

I wasn't even uncomfortable with the idea of being with Dean, I have been out for awhile now. I wasn't pressed about the parts of a person I was seeing, just whether or not they seemed interesting and didn't care that I have a toddler. That is part of the reason I had found it so hard to date after Hannah left. Fortunately, Dean had seemed to check of one of the requirements.

I mean who am I kidding? Is Dean even into guys? I mean when is the last time a very attractive auto mechanic who is all about cars has expressed interest in a guy like me, a nerdy looking school teacher? I try not to assume things about people but I don't think a guy trying to make a friend would seem so adamant about getting drinks with another man to the point he offered his brother as a babysitter.

That was another issue with this, who was Dean's brother? He mentioned he was one of my junior students, which meant I would see him in class tomorrow. Now that I mention it, no wonder my students don't know me that well because I can't even picture any of them sharing any resemblance to Dean. I should make a note to get to know my students better.

After managing to escape my thoughts, I finally searched for and located my phone wedged deep in my trench coat pocket. I dialed Gabriel's number. It rang for a bit before answering. Typical Gabe was probably out for an afternoon drink. Finally, he answered.

"Baby bro, what's going on?" He had a slight slur to his words so he was at least a bit buzzed.

"Gabe, I thought you'd quit the afternoon drinking? And, I don't know, find a better way to spend your time?" I practically yelled in the phone. I didn't want to catch Jack's attention because he was a truly nosey toddler. I continued the conversation in the living room, far enough to watch and not distract the kid.

"Whoa - ok?! Everything alright over there? Does little Jack need a visit from his favorite uncle Gabe?"

"No, Gabriel, Jack is ok. I just need some reassurance, I think some advice" I practically questioned. To be honest, I am not sure what I expected from this conversation. Gabe was good at listening to my complaints but his advice was tricky to follow sometimes.

"Ohhh is it woman trouble? Or a guy? I know you swing - well - all ways." I sighed so strong I sure he could sense my eye roll.

"Actually Gabe, yes. I believe I was asked out but I am not sure if the guy is even into men."

"Well if he did the asking, I'm sure he's at least curious" Gabriel said bluntly. He had a point. Dean had made the effort in asking me so even if he wasn't completely sure either he still wanted my presence to accompany him on a Friday evening.

"I think you should just go and have a good time. I mean the last you went out was for Michael's bachelor party last year, and obviously we partied wrong cause that marriage lasted two seconds!"

"Ok, I think I'll go. I mean he seems nice and it wouldn't hurt to at least make a friend out of this."

"Yep. A friend..." Gabriel went silent for a second. "Is he at least hot?"

"Gabriel!" I had said this loader than I planned, instantly getting Jack's attention. He came walking into our living room, which was weird because I last saw him in his high chair. "Papa, I escaped!" Jack let out a chuckle. I smiled back, mostly amused, but worried to see the mess left in the kitchen. I walked over to where Jack was placed only to find an empty plate and spilled milk all over the table. "Oh Jack..."