When Starlyre met Sapphire, he soon realized she was one of the rich girls in town. Letting his background show through did not necessarily feel like a big deal with her — as long as she keeps a secret. Fortunately, Sapphire has a reputation for confidentiality with her customers. Sapphire loves to share nice things with her fellow ponies, in return for building her popularity. She is generous by nature, yet she is something of a queen bee.
Starlyre grew up in the Royal Village, the capital of the Starpony Kingdom. His father is Jesse Heartsong, one of the wealthiest ponies who is not a royal. In Friendsville, Starlyre hides his true background because he wants to see who his true friends really are. Sapphire tells him he could use his position to his advantage. He could be a patron who gets favors in return for sharing his wealth. It can be a two-way street.
Star is still not comfortable revealing his privileged background. In the Royal Village, on the other hand, he has had no problem that other rich ponies know who he is. Because they already have so much money, he hasn't felt that they would like him just because of his money. But now he starts to have doubts. What if he were just a "commoner"? Would his rich acquaintances back at home act as if he were below them?
Conversely, does it really matter if people know his true background? Can it not be a mutual relationship — if his friends had to earn their standing with him? Starlyre reflects on his friendships with White Night, Princess Skysparkle, and Prince Endearment. Does he love them only because of their privilege? Their privilege certainly attracted his attention. But he honestly loves them as people. They genuinely inspire his love and loyalty.
Does it really matter if it's his background that initially attracts attention? It may help him get noticed — but a much deeper relationship might develop from there. That has been his own experience.