Sometimes I feel that what holds me back from asking is a desire to not be rejected, or not to look silly for asking. At the same time, I figure the worst that

Sometimes I feel that what holds me back from asking is a desire to not be rejected, or not to look silly for asking. At the same time, I figure the worst that'd happen is that they say no. That's where grit comes in handy. If you experience a lot of denial/rejection anxiety, rejection therapy tends to help as you acclimate to the feeling. Basically, do something where you'd get rejected a lot. Afterwards, if relevant, think about factors that could have led to the denial, and what could be done to mitigate them. This trains a more positive mindset in reaction to rejection. Alternatively, you could ask while internally expecting the denial. Plan around being denied. Having that fallback helps retain confidence, instead of letting 'what could go wrong' overly bother you. With this expectation, asking for what you want makes successes pleasant surprises!