Why does my guy friend (roommate) joke about dating me when he has already turned me down before?

Anonymous

My roommate is confusing. He and I had a fling a year ago and he turned me down numerous times since then... giving all sorts of reasons but none that really made sense or were solid. The only genuine answer I could get from him was... "if we were not roommates, maybe things would be different". Seemed like bs, but what do I know. Somehow, we still live together in relative harmony most of the time. We have talked about it a little since and the answer is still the same... he is not into it. Well in the past two weeks he has 1. asked me to be his plus one at a wedding and 2. made jokes about wanting to date me in front of his friends. Specifically he came up with and made a bet with me about something silly... loser takes the other one to dinner. Later on he said in front of his friends that maybe that was his secret way of asking me on a date. I am confused! Is this guy just playing with me?

Why does my guy friend (roommate) joke about dating me when he has already turned me down before?
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