It's better to give, but not if you're going broke!
Leo loves to entertain and be entertained. Your sign is so social, you're sure to have a few performing friends, from actors to comedians and musicians.
You may even be one yourself. Having tons of friends is great. Just don't feel that in order to keep them around that you need to pick up the check all the time.
Your generous nature may be only too happy to pay for everyone's fun nights out. But when it's not coming back to you, you may find that you need some better friends, a better job, or just simply better restraint.