I highly recommend working your way up to fine dining. When I was younger I worked casual dining and I would hope to walk to with $75 a day. That would be so ideal. But with fine dining I never walk with less than $200 a night. I also like that I work for a place that's closed one day a week. Hey man, even the most high got a day off. Take the time out to learn proper serving techniques, learn about different wines, beers & liquors. Cracker Barrel is nice if you're in high school, but you're right the money there won't cut it. I remember 4 of us eating there and our bill was $25. I'm not sure if you guys pool tips, but I left $10 because there was no way she was getting by on $5 a table.