I never payed more than $700 a month rent living in Chicago, maxed out my Roth, contributed to match for 401k even when money was tight, and max it out when I can. I have never had to buy a car - I rent one if I need, ride public transportation and cabs, and spend a lot of time walking/riding a bus or train. I've never paid for cable (but I pay for high-speed internet). I eat very well at home (and spend a lot on good ingredients, and shop for good wine under ~$10 when bought as a case - use the internet and magazines) and have become a fairly good cook (makes for great dates too, especially after a long day out sailing). I probably only eat dinner out once or twice a month, and don't buy my lunch more than once or twice a week. I bought a lightly used treadmill and weight set for my place, but still belong to a martial arts school that I suspend in the summer when I'm too busy. When dating, I found that women who liked to do things were more interesting than those who wanted to buy things anyway, and it's not a bad filter to start with. Plus, because I'm sailing, doing martial arts, etc, with my time, I have tended to only meet the active ones - partial self selection for fit and active people. There is more, but a lot of it is just structure of your life. I'm lazy, so I set my life up so that I'm not in the position of having to always resist temptation, or work against people around me. I set it up so that just following through with things I enjoy pushes me to where I want to go when I step back and plan for it.