1) Depends on who you date. Some can bring you misery just by opening their mouths, or worse, annoying you with their drama and insecurities through email, txt messaging, or IM's.
2) I tend to follow a monthaversarry cycle to keep track of dates. For one, it allows you time to come up with something fun to do, as well as being able to plan it out, thus maximizing the fun while minimizing the cost.
3) Here's where relationships do tend to kick me in the nuts. If I'm smart, I won't have to spend all that much, and she can be the happiest girl in the world. In the beginning of the relationship, thats how I tend to be. But as it drags on, I forget to be original and throw more money into it instead of being inventive. I'm always penniless, regardless or not that I have a relationship. It's either girls, tech, or inibriants.
There's much joy to be gained from a relationship, and I can say whatever I have put into any relationship I have gotten back 5-fold. Sure, some girls can be more burden than they are worth, but if you can find one that can think like you and appreciates everything you do for her, you can be set for a long time my friend.
A past girlfriend I had is one whom I terribly miss now. There little of the comforts of being single that I not willingly give up to be with her again. I think she feels the same, so hopefully.. well you never know