Will You (Hypothetically) Go Out With Me?

About a week ago I was invited out by Hobbes. Yeah, remember that guy? I’m sure all romantic interest between us is over, but he’s pretty fun to chat with so we still do that every now and then. In one of those conversations I had asked him about whether my spring trip would coincide with ski season, since I would be in Denver visiting friends and wanted to get some skiing in, assuming I could find someone to come along with. He mentioned that he would never turn down skiing, and I said I believed him, but that I also would never make plans with him again, ever.

He seemed to think that was pretty harsh. Let’s see, we had tried to meet up in Denver and in Chicago, at least once – and sometimes twice – a year, over the course of four years, and not once had we been successful. Yep, the Universe had made himself clear: Hobbes and I were not going to interact in person, and there wasn’t anything either of us could do to change that.

Hobbes clearly thought I was overreacting since he went on to hypothetically ask me whether I wanted to meet up when he’s going to be in Chicago for work. I responded fairly negatively, so he suggested I mull it over.

I don’t want to mull it over. I want to not have been presented with this scenario. It’s a Catch 22.

If I say no, the stars will align and he will be in Chicago, and I will be free, and then I will be that girl that’s too afraid to put herself out there to meet up with a guy she still talks to even though she hasn’t seen him in years.

If I say yes, the meeting will fall through. Maybe his trip will get canceled, maybe he’ll have to work late, maybe he’ll be in the burbs and traffic will be so terrible due to 12+ inches of snow it won’t make sense to keep the date (we did, after all, just have a blizzard). Some part of me will get excited about this meeting, even though I don’t think it’s likely we’ll actually get to the meeting part, and then that same part of me will feel bummed about it after. I’ll also feel really stupid, for not knowing better.

I told Hobbes to ask me again closer to this hypothetical visit, but we all know I’m going to make myself available in the end. Hypothetically, anyway.