If you failed massively at something in front of your crush, could that stop you from pursuing him/her?

This guy I work with, who had shown a lot of strong interest previously, just had a massive blow to career. He's very driven, and this was something he had no influence over the outcome whatsoever (he worked tirelessly to prevent it).

I am wondering if feelings of failure, inadequacy or even shame, might stop what was happening between us. I do plan on reaching out to him to offer some support/words of encouragement in the very least.

Has something like this ever stopped you from going after your crush?
If you failed massively at something in front of your crush, could that stop you from pursuing him/her?
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