[KMonte85]

The group thing sounds like a good idea! Get to know eachother without the awkward "date-ness" and pressure of one-on-one time!

[LanaBear]

Then maybe it would make more sense if we went somewhere alone? My goal is to kind of get to spend more time with him in different environments to see how it goes. I don't want to even have to worry about her maybe having to get used to the idea if it ends up being a bad one.

I think this is what you want to do. Personally, I think just the two of you for the first couple of times. Make sure you two hit it off before you start involving other people in your group, getting outside influences, etc.

[CHANDLERS WISH]

That's probably a good idea because you say he's younger and I don't know how old you are, but he may not feel comfortable around your age group of friends.

This will give you both time to test the water.

You just need a new attitude. With each relationship that breaks away in life, always be their friend... That doesn't mean you need to remain in contact, rather, it's okay, it didn't work, respect. Then it won't affect your friendship with your BFF nor her's with her brother... So make this notation to both of them this is your way of thinking in life, pertaining to "any" relationship.

It's natural to fear but the bottom line, if you adopt the above attitude nothing ever changes.

CW