I think I'm an ass

So I've been laying low trying to stay within my budget. I had just pennies in my checking account after I took my last $20 out of the ATM last Sunday. After I'd stayed in Friday and Saturday I went down to the bar on Sunday and had a beer while watching some football. I managed to make it home with $10 still in my pocket. But then I went to dinner with Lisa where she paid but I left the tip. That was the end of money for me except whatever spare change I could find under the seat of the car. It's actually fine. I don't use any money at work since I bring my lunch and coffee is free. I had all the food I needed at home. I had no gas in the car but I walk to the train so I could get by with out driving.
Last night I got a call from Carolyn. I hadn't called her in over a week and she was angry about it. "What could I have done to make you mad at me?" Yikes. I guess it's better to get a reaction then nothing. I assured her it was not my intention. Well, maybe that's partially true. Mostly I figured anything I did would put me in a position where I had to explain how broke I was. But I also am feeling frustrated about how I'm always just a friend and there needs to be more than that. I don't feel like I'm ever going to get to be "the Man" again. It's easier to just stay home.
I felt obligated to make amends so tonight the plan is to take Carolyn out. We will see how that goes.
It occurs to me that perhaps I've been to passive. If she wants me around that bad I may ask for more than "just friendship". I'm not walking away but I need to know if I can look around. How to explain that is what is really hard.
Then on top of all this Lisa says she wants to see me more. And I called Janet this week and told her we would try and get together soon. And as my friend Jimmy said, "You're not banging any of them so don't get all worked up."