When does something nice become something more

I'm not one to believe all the fairy tales about Prince Charming and Happily ever after (No I have not been watching Shrek), I'm more of a realist when it comes to love. Well most of the time. I haven't had a good track record in the last couple of years and I'm working to correct this flaw. That is why I wonder when exactly is it when something nice turns into something more?
I've been talking with a guy friend from a very long time ago, well he still is my friend, it's just that we once/twice dated nearly 20 years ago. Since then we have been good friends for as often as we see each other, which surprisingly in this dead one horse town amounts to about once or twice a year. With the advent of Face book it has become easier to talk without actually being in the same room.
This has led to something akin to dancing in a minefield while wearing track spikes. Sooner or later one of you is going to step wrong and BOOM! The first misstep was was nearly two years ago when we were suppose to attend a football game at the local high school. This counts as the cheapest date one can half in this backwater without splurging for a fishing license and a foam container of night crawlers. He backed out at the last minute, leaving me high and dry with $6.00 wasted on a ticket. Not only did he back out, he RAN, disappeared for weeks online and in real life. I didn't feel hurt after about the first 24 hours, but man was I angry.
Fast forward two years and once again we are engaged in the same dance and I'm left wondering something. If we can so easily fall into this pattern of flirting and planning to hang out as friends, how do things backfire so easily? When, if ever will it become something more? If I am left holding the bag again can the friendship that we've shared for 20 some years survive or should I just give up? One thing is for sure, I'm going to have to nail his sneakers to the floor to keep him from running again until I can at least find out if our being so nice to each other can grow. I'm not looking to move fast (that will just end in disaster again) but quite honestly, I'm being lapped by a two-toed sloth right now.