I'm a photographer with a brand new freelancing business and my boyfriend is in his last year of law school with lots of expenses for the bar and preparing to pay back loans. We both know the other one is concerned about money. Not quite in the red but very cautious and careful. We try to do one thing a week with other people and one thing a week just ourselves. With other people it's often a potluck at someone's house - it allows for everyone to try new things or just to relax about not going out for food. For ourselves we tend to use up the "gift card tips" from my job (as a thank you I've had a few couples send me gift cards along with a note) and old christmas gift cards through the year. Hiking is free. Last summer we trained for a half marathon together (I'm the runner) and he taught me racket ball at a local college gym (his hobby) - if you spend the time learning from each other's hobbies it usually ends up cheap and a way to get closer.