Another dating rant

Where do you draw the proverbial line?

Gregory is a nice guy. A VERY nice guy. Nicer than most I've met. But he's a sad guy that's down on his luck. Searching for love in all the wrong places and faces and somehow, he found me. All that keeps ringing in my head when I am around him or when I think about him is what my psychic cabbie said..."there's perfection in imperfection." I know that I spend so much time dismissing dudes romantically when there is something that's not in place. With this guy, I've been in a constant tug of war.

At first, I entertained the thought of having someone in my life that I know would pamper me and treat me with so much respect. There was just one little problem/blemish/imperfection, he's completely BROKE with a shaky living situation. Hmm. Now, that's an imperfection if I ever heard one. What to do, what to do?

When should I take out my pencil and draw the line? When do you say, that's it, I can't be with someone like that. I want to blame him. He wants to be in a relationship so badly, he doesn't care that his life is incredibly out of order. When I am with him, I want to be with him. Part of me feels like that is because of pity and not truly wanting to be with him.

I hate when people say, when it's right, you'll know. Maybe it's because it's never been "right" with me, so I've never known. I always feel so uncertain when it comes to dating and if I truly want to be with a person. My heart used to feel a vacancy, because I felt love never lived there, but now, I know that I am capable of full and complete love, but am I?