From what I've observed in life, people often ask questions about things they previously failed at and later succeeded in. While they found these questions strange back then, they now ask the same questions themselves. This is quite strange. For example, after having children for a long time, parents who haven't had children begin asking those who haven't yet had children about babies. Frankly, those who haven't had babies are uncomfortable with these kinds of questions. Those who have been unemployed for a long time, once they get a job, start asking hurtful questions of those who are unemployed.

I've noticed that this behavior is common in many people. Even the most thoughtful people make mistakes in this regard.

You can try pajamas or sweatpants instead of pants, they might be a little more comfortable and acceptable :)