Why is it that dating women/having relationships is such a pain?

I think you answered your own question really. But to add to it, most girls want to be settled down by the time they hit 27. If you are dating younger girls cause they are more attractive and "fun" you are going to get the drama that goes with it. My advice is to find someone that is more independent, maybe a little intimidating because of age or success. Enjoy your time together, enjoy your time apart, respect each others careers and hobbies, and if you find a match made in Heaven you will grow together and probably want to settle down and start a family. Don't rush it. You are still young. But sometimes the hottest girls have the most drama and the least stability. You might have to give someone that is not normally your "type" a chance if she seems more stable and genuine. But that's just my two cents. : )