Should I feel bad even though he kind of set these conditions for us dating? Should I break it off?
Most Helpful Guy
He has agreed to all of this with the hope that you will develop feelings for him when you see what a wonderful guy he is. Unfortunately, the heart does not work like that; you will not develop feelings and he will be even more devastated when you leave later. Better to do it now.
Here is the rule: Follow your heart into a relationship but follow your head out of a relationship.
Most Helpful Girl
That's really kind of pathetic for him, isn't it? A bit, unfortunately. Respect him enough to stop seeing him, because he is either so attached already that he wants to continue to to be closer to you, which is unhealthy, if you don't reciprocate his feelings, or he's hoping that if he spends more time with you, he can make you feel the same way about him, so it's kind of a manipulation. Sounds like the contact should end there.