An artist I follow recently had that dilemma. What came next was one of the cutest interactions I've ever seen, and I had to share it with you.
This person had admired one of the other creators on DeviantArt for a while. She was one of his first followers, and he credited her with the fact that he'd put so much effort into his ongoing fancomic.
He loved the cuteness of her art style, and he wanted to be friends with her. But he didn't ask, because he was shy and worried that he'd just be a bother to her.
One day, he mustered his courage, made an epic-looking piece of fan art for one of her original characters, tagged her in it, and explained in the description how much he respected her and wanted to be her friend.
You know what she said in response?
After spending a few paragraphs gushing over the awesomeness of his fan art, she told him she had wanted to be friends with him!
Why didn't she ask, then?
Because he seemed so busy, had such detailed art, and had so many followers, she'd thought she was the one who would be a bother!
A couple replies later, they were discussing which sites or software they'd use to chat with each other.
Will it always end that way?
Probably not every time, but you never know until you try.
In most cases, the worst thing that's likely to happen is that you don't get a response.
If that happens, it's probably nothing personal. Some people really are just that busy, and if they replied to every message, comment or friend request they got, they'd never do anything else.
If you aren't comfortable with outright asking to be friends, you could start out with something more low-key.
Show your interest and conversation skills by making insightful comments about their stories or art, or by asking questions about them, their characters or their work.
If you're up to it and you feel like the time is right, maybe ask if they'd be interested in chatting sometime. Find out which times of the day and week work best for them, and which methods they prefer to use for conversing online.
A quick disclaimer:
This advice only applies if you actually want to be friends with them. If what you really want is to get fame or exposure through being friends with a popular person, they probably won't appreciate it, with good reason.
But if you seriously want to strike up a friendship, go ahead and ask.
Some will say yes. Some will say "no" or ignore you. Others (like me) might prefer to let the friendship grow naturally rather than just declaring it official right off the bat.
Whatever happens, it won't be the end of the world, unless you REALLY don't handle rejection well and you have access to a doomsday device.
Sure, the possibility of rejection stings, but in my opinion, the chance of a great friendship - and of making your favorite artist's day - is worth it.
Is there a person you've been wanting to make friends with?
Did this blog post inspire you to take the leap and reach out to them?
I'd love to hear from you!