Buddy-sour Horses

What is the best way to get a horse fine with going out alone? One horse that I frequently ride (used to be mine but is now my cousin) is mostly an angel on the "trail". But I tried to take him out alone once and it didn't work to well. Both Ronnie (the horse) and I have been arena babies, so I don't have much confidence and just got off and led him home. Yes, I know that was encouraging the behavior, but we were right by a road and I wasn't in the mood to die
Also, I'm seriously considering buying friend/ex-trainer's 2 year-old gelding. (I get to help break him! Haha, so excited.)

Can someone tell me how to cure Ronnie of his loneliness? And how to best get the colt, Ryan, used to the trails and riding them alone. thank you :)

What I would do is start by ponying the younger horse with a older, steadier horse that is good on the trail by itself, no problem. That way, he can get used to being on the trail and have the confidence of the buddy system being right there. Really build a strong relationship with him by doing ground work, grooming, feeding, ect. This can help when it comes to backing him and so on later on in the future.

And, if you dont have any confidence, the horse wont have any confidence. Start going out on the trail with friends and their horses at the barn where you are at so you can get used to being on the trail. When you are alone, the horse looks to you as a leader. They need to be able to trust you. But when you are just as nervous as the horse, that does no good. Hope this helps, keep us updated on your progress!

You could just lead him out a few times, so hes used to your company instead of another horses. Let him see everything wiht you right there besides him.

Also keep the first rides short so its not to much for him to deal with.

Also if you have access to farm land , have a go there, as its kinda an inbetween step from an arena to completely open road/trails and such.

What exactly does he do wrong when he's out alone? Does he spook more? Or just plain silly? Please describe!