1. As mentioned in the lesson, 得意 has a more positive meaning than 骄傲.
2. Note the usage of 猜得到 and 猜不到.
a. 我就不相信你猜得到
b. 可是我觉得你还是猜不到.
3. These lessons on games are a great way to observe some more natural speech between the speakers, in this case, the playful banter that may occur when two people are competing against each other.