Am I the only one that feels this way? Does anyone else feel embarrassed at the thought of begging friends, family and strangers for money?
No, you are not alone, although I'm not embarrassed exactly. I just don't like asking people for sponsorship like riding a bike over a typical charity ride distance is something unusual for me now. I'm doing a 100 mile day trip later this month, for fun, along with friends and hundreds of others. It would need to be something truly epic to be worth sponsoring.
This attitude now extends to most people who ask for sponsorship for riding: I know most of them have done long rides before and probably won't struggle too much to do whatever one they're asking for money for now. I get a bit "ride if you want to" about it, but you can't exactly say that to them, else you get labelled as some sort of meanie. I don't mind giving money to charity, but I do mind paying people to ride. It really shouldn't be anything remarkable.
As you may have noticed, I get really grumpy about the big "charity" tour operators where the first £x00 goes to the private company organising the tour and paying for their PR staff to get the organised-begging-pretending-to-be-news into the local newspapers and so on. They're really not helping to make cycling commonplace because it suits their fundraising to present it as an extreme endeavour.
So I'm trying to limit the number of charity rides I do and only ask for money for one a year. As far as I know, I will be taking part in one charity themed ride where we'll be taking a collection along the route to the lifeboat station; plus I will probably take part in two other rides - so at one, the donation will only be from me.