My Weekend Spending Has Run Amok

The last several weekends I've spent way more than is necessary and/or reasonable. Let's see if I can break down this weekend.

Saturday:
$0, other than groceries. I stayed in and napped and read and had some alone time while my boyfriend went out with a friend. It was nice.

Sunday:
1) Feeling virtuous after a) spending nothing the day before, and b) cleaning the bathroom, and also running quite late, I decided that it would be fine to "spend" the $20 my boyfriend owed me for groceries on a cab downtown for a friend's poetry reading. The reading started late, meaning the cab was unnecessary anyway. Boo.
2) There was supposed to be free chai at the reading, but it turned out to be a myth, and the pressure to order was quite intense. I went in on two pots of chai for five people: $5, my portion covered by my boyfriend (hang on, this is a theme)
3) Went to my parents' apartment to do a test-run of Thanksgiving pies. Expected to find them in, or to find something we could make into dinner. Found neither. Ordered in sushi, $25.
4) Got a call from my parents: out for my uncle's birthday, at a country-western bar featuring a singer they've been raving about since they returned from Texas recently. Starts in ten minutes, hurry. Cab: $8, covered by my boyfriend out of the money he owed me for sushi minus the money I owed him for tea (sensing a theme?). Thankfully, my dad bought my first beer and my aunt bought my second.
5) Since I still had to do the pies, back to my parents' after drinks & a long set. This means waking up late and taking a cab to work (withdrew money from an out-of-network ATM: $3 in fees, $8 for cabfare). It also means I didn't pack lunch despite buying groceries on Saturday to do just that. Lunch: a predicted $10.

Appalling total: $66, plus the $32 I now have in my wallet. I hate cash, mostly because I blow through it so easily.

Boo.

Things for future attention: I have the sense that this you-owe-me-I-owe-you business with the boyfriend is serving neither of us, financially. It's fake money--it doesn't quite feel like one is spending it on either end, either incurring the debt or trading something else to pay it off. It's a bad idea. I'm not quite sure what I plan to do about it--should we pay each other in cash, or just scrupulously avoid covering each other's debts, or what? (Aaaargh!)

Planning. Planning will help me avoid these things. As will leaving time for public transportation and not always running late. Basically, cabs are my "latte factor." Cabs and Diet Coke. The point is, though, with better planning, about $48 of the onerous $66 would have been unnecessary. Planning.