26 is THAT old?
I'll have to agree with PM Mama. I find some of the comments on the borderline of being offensive and ageist. There's different standards on different campuses. I don't really think the fraternities at my school would mind pledging someone like Jestor, as long as he fitted in. In fact they have. We just initiated a 25, 27, and a 29 year old. Two of them fit in my org and on campus as a whole more than some of the 20 year olds that I know.
Over half of the juniors or seniors has transferred at least once. What's wrong with transferring five times, if you thought the schools sucked? What's wrong with changing majors if you find out what you majored in suck? While this appear to be a commitment issue, it may not be the case. He just might have high standards. If he finds something he likes, he probably will stick with it. I was a member of an interest group for one sorority, and then I suddenly pledged another. After a few months, I wanted to drop out and pledge yet another sorority. Whatever I was looking for just didn't hit the spot. Then I found APhiO, and I have sticked with this for the last few years. I also majored in many things (not at the same time) as an undergrad. Fortunately, many of the courses within those majors overlapped.
So, Jester, if you really really want to do this Greeklife thing, I suggest transferring to a commuter or semi-commuter school. Peeps are much less uptight. I would just keep quiet about being a wedding planner and getting teary-eyed.
Slightly unrelated question, are YOU paying for your tuition? Sorry if I missed this. You are an adult now. I think adults should be able to do what they want as long as they don't hurt other people. Being an adult isn't only about being married and having 2.5 kids. It's also about making your own choices and accepting its consequences. It should'nt matter if you were 40 and still in college. Those kind of people would not be my cup of tea, but hey as long as they are paying for it with their own money it's fine. It would be unfair if you were in school this long and your parents were paying for it. I hope you are paying for all of this out of your pocket.