I have never regretted asking for something I wanted, as long as I was prepared that the answer might be "no." It's all about mindset.
Don't give in to the temptation to over-analyze a situation - it's a waste of time. Remember when someone says "no," that's exactly where you'd be if you hadn't asked.
Asking for help can feel awkward, especially when asking someone for a favor. But, I just remind myself that they're adults and they can say "no" if they don't want to do it. Sometimes a "no" is a blessing in disguise because that person may have a friend who can help, but they wouldn't know to connect you unless you ask.
We all need help from time to time. As long as you're not needy, people are happy to help, but they can't read your mind.