The not looking like a controlling girlfriend thing is something I have to work on a *lot*. It's a really hard trap to get out of. There's this media image of a controlling, high maintenance girlfriend. She's really jealous, won't 'let' her boyfriend have any fun, takes him away from his friends, demands gifts, screams at him if he forgets an anniversary...there are countless jokes about this kind of relationship. Then there's the 'cool' girlfriend--all of the guys want a girlfriend like her! She never expects presents, but would rather sit around playing video games with the guys! She doesn't care about Valentine's Day! She's not jealous at all, in fact is happy to check out other girls with her boyfriend!
Some of these are close to me, but they aren't *all* me. And expecting to have promises kept does not mean I'm the Controlling Evil High Maintenance Girlfriend. No, a guy isn't 'whipped' (I hate this term) if he chooses his girlfriend over his friends most of the time. And a guy who treats his girlfriend like she's asking for diamond-plated shoelaces if she wants to go out for a nice dinner is not worth my time. But it's hard to believe that in my more irrational moments.
I don't have any real advice, and it sounds like it was a non-malicious mess up on Ryan's part, but I just wanted to express empathy for your reluctance to be 'demanding', even when your demands are totally reasonable.