In that case, should you try to fake your own situation as to not get pity or should you be honest? When I encounter people who are financially ahead than me I just think that it will be me someday... That I will reach that level too where I would be able to buy whatever they can. So basically I try to make them my inspiration. Do you take inspiration from the rich people or do they make you feel worse?
There's a saying that wealth attracts wealth and this kind of situation is the best time to apply it. When you have friends that are doing well, you ought to fake it to fit in the circle and hope to benefit from opportunity that might come any moment. If you looked pity in their midst, they will only see you as a liability and you'll lose being part of the squad. There's nothing wrong faking it to earn opportunity but there's everything wrong with faking it to deceive yourself. What matters here is the purpose for your faking actually. Envy the wealthy will not make you one, faking it will not make you one either but being in the circle will give you clue on how become one.