Does it ever work out the 2nd time around?

Well, I've tried it twice. With two different guys. It's never worked.

:)

Not unless what broke the relationship up in the first place has changed. Quite frankly, it's rare that people change those sorts of things about themselves because they aren't quick and easy changes to make. Relationships don't end because someone makes cookies with raisins instead of chocolate chips which is easy to change. They usually end because of personality traits which aren't easy to change unless the person has a mission to grow into a better person but when that happens they can actually outgrow the other person.

I am sure it works out sometimes but I think that more often it doesn't end up working out.

It might, but then again whatever happened the first time around to cause it to end might still be there.... only way to know is to try i guess... good luck :)