This dude sounds WEIRD. Like he needs a therapist and not a girlfriend. Most of the time I'd say to stop messaging him back but you seem to be mostly doing it for the lolz at this point so.
Re: my guy that I mentioned. He was in the habit of messaging me on Skype every time we were both online ... I think I went first only once last week. But then yesterday I had to message him first, and today I notice he's there but not messaging me. Do we think lack of interest or him trying to avoid liking me as per the statement I showed you guys or does he just want me to make the effort?