Trust Fund Baby

So, my "friend" and I were having lunch today and he made a comment about how children who inherited trust funds grow up to be spoiled, selfish,  and have no work ethic.  I'm not sure why he was speaking so harshly on the subject but, he's young so any passing thought he has he makes into a huge speech.  Anyhow, his apparent annoyance for trust fund babies continued and I just had to say something.  I mean here I am trying to eat my salad and stare at his messy hair that falls into his beautiful brown eyes and he's bitching about rich kids.  When he interrupted my day dreams with his bitching I told him that, as a matter of fact, I was a "trust fund baby" and that it ain't all it's cracked up to be. 
First someone you love has to die in order to leave you a trust.  In my case it was my father who actually brought love and warmth into my home when I was a child.  When I was 13 he died.  My mother became even more icy and I lived the rest of my teenage years trying to get the hell out of the house.  Yes, having money is fantastic, it's great.  But, I would give every penny back if it meant that my father was still alive. After saying this, my "friend" looked at me like puppy who had just been scolded and apologized.  Then I realized that it's not his fault he doesn't know anything about me.  I mean we've been, urm, umm "friends" for 10 months and I don't go out on actual "dates" with him.  He's never been to my house, nor I to his.  Of course, he's never met Margo.  Although, he does know about her.  Really, today I came to the realization that for the past 10 months I've been sleeping with a complete stranger and I thought to myself, what's wrong with this guy?  Or really what the fuck is wrong with ME?!!! My head has been in the clouds (or pillows).  So, the next question I am poised to ask, What should I do next?  Do I care if I'm 10 years older?  Does it really matter that he's an intern and earns as much money a month as I spend in one shopping trip to Macy's?  Am I using him for sex? Or is he using me?  Am I a cougar?  At 35 can you be a cougar?  He does have a degree...that's one thing I look for in a guy.  He's very sweet. Is it worth it?  I've been burned so many times, is it really worth it?   What the fuck and I going to do?!!  So, yeah, I think I'm going to stop watching the surf and ride the wave and see where things go with Jacob.