I know it's been mentioned but Splitwise is an AMAZING app/webapp. I've used it with friends on vacation (uber rides, hotel/airbnb, dinners, etc), I've used it with roommates (electric bill, rent, etc), and now I use it with my boyfriend (rent, groceries, utilities, furniture, tools, etc).

I find it really helps me as I HATE talking about money and asking for it (even when I'm owed it). This way I never feel like I'm paying in more than he is and he doesn't feel like he is paying in more than me. Some months he "pays" his portion of the rent by just buying all the groceries or buying something else we both agreed on getting and it all evens out. Because of this we rarely have to actually settle up but when the balance gets out of wack by like $500 one of us will just venmo the other one and record it in splitwise.