Hi Jeni! Good for you for helping a new person get drawn into the sport... it's awesome that a 16 yr old is showing interest in such a great and healthy hobby!!
I actually ride with new people on Sunday AM's... a sort of informal introduction ride group... I talk about safety, technique (spin, spin, spin!!!), getting fit to the bike etc... when I take people I have a route that is 24.8 miles COMPLETELY flat... most people that have never ridden cannot touch hills until they build some initial strength in those quads... especially since they are probably riding flat pedals (so not able to utilize all muscle groups yet) ... and still scared to death of clipless! I have a no-drop policy so that a brand new person can ride with us if I have more experienced people with me... sometimes we don't make it the 25 miles... I can look at newbies and sorta tell if they're gonna poop out early...
I also talk about eating prior to and during rides and I remind people all the time to drink!!! Amazing how many people don't drink... often times I suggest stopping to drink as they are not comfortable removing the water bottle while riding... another thing I teach people how to do! I just have to know this is completely a recovery ride for me... and if I want more I go back out after they all leave!
When I was brand new I was riding with my ex, a racer... and his expectation of what I should already know and be able to do was unrealistic... I almost quit due to it... it was just freakin miserable... got divorced in Dec and have done 4 centuries this year so far... HA!
I know what ya mean about getting dropped by a peleton... LOL... makes ya wanna chase that rabbit down huh?
good luck with your new boy and way to go on encouraging him!!!
There is a fine line between "hobby" and "mental illness".