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HELP! im in such a weird situation.....

Tell him you're on to his game and you want no further contact. Kiss that money goodbye and don't do it again. This is a con and an habitual liar. If you don't want to be so direct, just tell him it's not him, it's you and you have something going on in life and you need to breakaway.
 
I would break up. The whole thing seems sketchy and I wouldn't want any part of it. But that's just me.
 
Speciesbeing,

Just in case you check back in with this thread. . .

After reading your hesitancy to firmly put an end to this "relationship," I started to get strong warning vibes. Two assholes does not a pattern make, so it's possible that you just happened to get involved with a liar and manipulator online as well as an asshole in Chicago. However, "dating" two assholes and resisting an overwhelmingly consistent bunch of advice to get rid of the one who is still around suggests that you might be prone to date guys who are going to take advantage of you and then not have the heart/strength to ditch them.

Be careful you don't continue to involve yourself with the same kind of guy over and over, getting your heartbroken every time.
 
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