Well... do you think encouraging them to experience new things is likely to make them happy?

Yes, and I wouldn't do it if I thought it would make them sad, but, I don't do it just because it makes them happy. I feel I can understand a person more deeply if I am with them as they react to new situations; it makes them feel more human to me and increases my ability to empathize.

For me, it's just tiring. I want to be making people happy, not competing and winning. I like doing things that are awesome, and I like doing things that are challenging. But I don't enjoy defeating people

The more I reflect on them, the more complicated my feelings on competition and winning seem to be... I want to be valuable to other people and accomplishment proves that I have the necessary ability; for example, if I do well on an assignment relative to my classmates then they will ask me to help them in the future.

But I also feel like there are competing forces within me. Winning leads to praise which helps me with insecurity but this bothers me; I want to be at peace with myself so I can focus on other people. If I won and it didn't make anybody like me, I would just feel empty. I know other people can value for me for who I am rather than what I can do, and it is really important to me to learn how to accept this.

As for whether any of this is masculine or feminine I don't know... I'm mostly happy with how I am inside, but often not happy with how I express it. I do love feeling at peace, and so want to recover from my insecurities.