I just finished reading No More Mr Nice Guy, and never even realized how poorly I deal w/ this situation. I grew up in a household where we were taught to be a woman "pleaser" which obviously really sucks for attracting women.

As an example, my girl called me yesterday a little tipsy from the Christmas festivities, and I mentioned that my brother and I were going to go visit his wife at work (she's a bartender). She immediately changes her tone to a more serious one and mentions that she was just calling to see if I wanted to come down there (she was celebrating Christmas w/ her best friend who I've just recently met). Two problems: 1) I already made plans and 2) It's almost an hour drive. I tell her I'd love to come see her, but already promised my brother we'd hang. She normally wants to talk my ear off, but suddenly had something they had to do, and she just tells me to call her later.

Not a super interesting example I know, but I feel like having to say no (even a "soft no" like this) is something I definitely struggle with. Immediately after, I always feel the need to fix the situation somehow and make her feel better despite me doing nothing wrong. How do you guys handle a disappointed (not angry...she knows that would be crazy) girlfriend? Do you let her wait it out and come back to you or reach back out to let her know you care?

The key is to reject her requests without the inherent "guilt" for doing so. Girls feel that and push even harder for what they wanted. You should not provide her with logical explanations but tell her this is where you want to be (like in the example, hanging out with your brother). Also, make it seem like "It's no big deal" when you say no. If you expect her to make a big deal out of it, she will make one.

Think about getting her to make the effort, e.g. "You and your friend should come here, we're having so much fun". When faced with the prospect of driving one hour to see you, she will think twice about making such requests again. Women have grown accustomed to men satisfying their every whim to the point that a man who does not jump when she asks for something is at first thought of as rude then valued for being different.