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I don't give most men a whole lot of credit these days... so my theory is:
He may be trying to keep you there, hanging on for when he needs/wants you around - when it is convenient for him.
The comment about Cuba (whether it is true or not), could be to show you "hey, I'm a desirable guy that nay girl would be lucky to have" and to make you think "oh, he's so sweet, he must want me." Normally I would think this would be a good situation, but the fact that you have been dating on and off for two whole years (normally if someone is going to commit it is before that) and the fact that you kind of make it sound like this isn't the first time he's blown you off, makes me think the comment was not totally innocent and cute. It's keeping you around and interested, but not too close.
Of course we analyze boys too much, James... it's our job!
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