In "Seventy-Six Dollars," Monk's superpowers help him get what he wants from Angel, but they also prevent him from getting what he wants from her. How?

Because he can read her thoughts, Monk is able to win his bet with Angel and get her to eat lunch with him. He is on the verge of winning a second bet which will force her to go see Star Wars with him, but because he can read her thoughts, he also knows that she promised to see Star Wars with Justin this weekend. Knowing this, he alters the bet so that she only has to walk him to class and hold his hand. Basically, because he can read her thoughts he can win the bets, but because he can read her thoughts he begins to feel bad about winning the bets.