Would I be a jerk if. . .?

See, I have this dilemma. A friend of mine here in Chicago seems to be kind of, well, in love with me for lack of a better explanation. A very long time ago, when we first met and before we were friends, we had a fling (and by fling I really mean one night stand). This fling is totally common knowledge amongst pretty much everyone we know because we kind of talk and joke about it constantly.

I was kind of a bitch to him right after it happened because I was a big raw emotional nerve still smarting from a really scarring break-up that happened mere months before and because I didn't really know him and kind of assumed he was just a tool (because nice, good guys were not as useful in my sad little brain as jerks were in getting back at aforementioned ex-boyfriend who had no idea any of this was happening--yeah, I know that makes no sense but it is an accurate representation of what my brain was thinking at the time, I told you I was a hot mess).

Then we got to be friends, and we are both part of the posse that moved from the University of Idaho to Chicago, and that group has formed a sort of family unit here. We hang out a lot, we celebrate family holidays together, and we overlook the fact that some of the people in the group have no love for others of the people in the group (Brian Bush and Angie are the example there), but we just decide to be together in spite of that--just like a real family. Now not all parts of this group spend equal time together. There are the girls who watch silly movies, and no boys come shopping with Schlegs and I (except sometimes Plummer in capacity as gay best friend), and there is the baseball fanatic group, and the football fanatic group, etc. The person who is in love with me and I tend mostly to see eachother only occassionally at the big whole "family" events.

Last spring, I first noticed the, "Hey, I think he might think he likes me!" business, but he had just gotten pretty horrificly dumped by a way serious girlfriend, so I chalked it up to a crush that would soon pass, like over the summer which he was spending in New Mexico. But he is back, and it seems not to have passed. It might have gotten more serious.

Now pretty much all of our friends here would be thrilled if we got together, and he is a good guy and I admit that there is some palpable attraction between the two of us, BUT (and I know you all knew that was coming) here is the thing. If I felt this way about a guy, just a random guy who nobody else really knew, I would for sure pursue it in a casual, "Let's just have fun and see where it goes," sort of way. However, I don't think this guy sees us in those terms, I think that he would see anything starting between us as FOR REALS. We jokingly compare him to a girl (and he once said there is a tiny little vagina in his heart--to defend his tears during "The Notebook"), and in this case it is true--he would play-forward the relationship in his mind (probably to our wedding/happily ever after) like girls are generally assumed to do.

Now, if this was again just a guy, that probably wouldn't give me too much pause, but he isn't just a guy. He is part of my family here, and if we didn't work out (and I am not really feeling this as more then just a for fun thing instead of a massive relationship thing), what would that do to our entire family? I think that would be rough. I also think it would especially suck to be the villain in that piece, and it seems very likely that that is exactly what I would be, so I have chosen the path where I just leave this alone unless I start to feel that I would be interested in giving this a big serious relationship go.

All that is background to the current dilemma. He has asked me to go with him to the opening of The Crucible at Steppenwolf. It would mean a free ticket to the show as well as an invitation to the cast, crew, important donors opening party because he works in their costume shop and as a member of the greater crew, has earned a spot for him and a +1. Now, he didn't couch this as a date in any way, but this will be the second or third time he has chosen me out of the group of our family and friends to get to do something like this. In fact, the only time he hasn't chosen me, he took Brian Bush when they lived together or he took the now ex-girlfriend, or he took all three of us, and that was before anyone else lived here. Since the others have moved here, and he has lived alone, he only seems to invite me. So, I have a suspiscion that he is using things he knows I will find irresistable to end up on a date-like situation with me. I really want to go, but I don't want to be a total jerk and keep using him in a manner that kind of feels like stringing him along. I really don't know what to do because I feel like I either get to not be a jerk or go to the fancy-schmancy opening. Any sort of help, advice, perspective is totally welcome in the coments.