Chicken of the Sea?

So a week and a half ago I called a good friend of mine (let's call him Ryan) that has watched me through quite a few dating dilemmas just to chat and catch up. Inevitably my love life came up. I told him it was a total disaster, there were 3 choices one I really wanted to pursue and 2 backups that I could pursue if I put any effort into it. Of course the more interesting story is the one I want to pursue so he asked for the short version: He's been emailing me for almost 4 months, we had plans but due to an awkward situation with his ex I cancelled and now he backs out of everything and claims to be shy at dating. In a reply that very few people can get away with he told me "you're being an idiot. I have to go but IM me in the morning and I'll tell you why" of course I IMed him first thing the next day. Here's his theory:

He watched me have a similar "relationship" with a guy all through college (lets call him Scott). The boy was very cute, very social and had tons of friend. He was also very uncomfortable with dating and consequently it took YEARS to sort things out. This is sounding very familiar to me right now. His argument is that Jason is very social in every way except dating and just like Scott they both take dating very seriously, he says this is my "type". They will hang out with friend go to things, even hang out with girls but when it comes to dating they like to be more cautious and they don't like to put themselves out there to be hurt. I also come across as very social and outgoing and if I want to do something I will find a "date" and go and not think twice about it, unless I actually like the guy in which case I have to really pep-talk myself first. To the untrained eye (pretty much anyone but a very few select friends) I go on dates like crazy and am not intimidated by boys. So here's why I'm an idiot. Jason invited me to go to the movies with his friends- he probably feels comfortable enough in that I won't totally embarrass him infront of his friends but this way he can easy into stepping up the relationship from digital to an actual relationship. I said yes so he was all excited and then I cancelled- he was disappointed. I turned around and invited him to the fair which for me was a big deal since I like him but to him he was no different than any of the other things I do and to him it was more good timing at being around when I needed a date so when he cancelled it did not even the score. In my mind I was waiting for him to ask me out but in his mind I haven't really demonstrated much of an interest and I've already burned him once so the solution is I need to ask him out on a date that will be just us and make it obvious it is a date. (thank you to friends that can tell it to you how they see it- he justified this with a few stories from the Scott era) He argued that it wasn't too late and that he would have stopped emailing me if he wasn't interested and the emails were shorter because he was getting frustrated

So with that in mind, I sent an email: This email and FB thing is fun but I'm much more entertaining in person. I have a proposition: I love halloween and have never been to a haunted house, you love all things haunted so lets go to a haunted house. tonight. (the other argument was that I needed to do it quick rather than give him time to think things over) I got a reply of "Alas, tonight and this weekend are booked for me. But a haunted house does sound like fun, and I'm always up for fun. I'm sure you are fairly entertaining as well. I'm really not. I just put up a front when I go in for interviews and online messages. So be prepared for my shell. Next weekend has plans in motion but I'll know for sure hopefully this weekend what will and will not pan out. What are your plans for then?" we made tentative plans for the following Friday (this past weekend) pending the plans of a buddy that he had coming into town. Monday rolled around and we emailed and talked about the haunted house, tuesday and wednesday we didn't talk at all and thursday it just didn't come up. I finally asked if he were one and got, I can't believe I forgot to tell you, I can't go. My friends are going next week, why don't you come with us though?

My thought we had he said no outright to the haunted house I'd be done emailing. Whats the point of constantly emailing if nothing ever comes of it? He said yes but now keeps changing the plans so now I'm at a cross roads. There are a few possible explanations I have some I came up with and some are other opinions. I'm really not sure what to make of it.

I've gotten close to 300 emails from him over the last 3 and a half months so that he is interested in not up for debate but where to take it from here sure it!

#1- "Face Value"- He really did have plans, I should take the reschedule and not think twice.

#2- "Chicken"- He really is scared I won't like him when we go out. Over the last 4 months he's built it up in his head making it even more intimidating so I need to just be patient and go with him and his friends- he'll probably be more comfortable with them there and act himself anyway.

#3- "Too Many Fish in the Sea"- He is interested but also has a few other girls and not sure how to handle the situation. He doesn't want to limit himself or cut off any options. The rescheduling it to string me along until he can make up his mind. I should just tell him either we need to actually do things or we need to stop emailing and move on.

#4- "Everyones Friend" - He never pulls the trigger for fear of rejection, I should drop him now, he's had plenty of chances.

Ryan take is a combo of 1 & 2- he keeps trying to fit it in but it also scared so that is why he chooses the other options and that going with his friends will give him a wing man and also make it harder to back out (its harder to cancel on a group than one person) He also says that I am always attracted to this type and work great with them once I get past the initial start-up so I should just be patient and go with it and unless he flat out cancels take it as he's trying.

I'm open for advice. I'm not sure how much longer my patience will hold out.