Why is my dog so skittish?

Toby sounds like a high-strung, nervous dog to start. Your little games of sneaking up onto him and scaring him has backfired---onto you!! When you have a little creature like this around---calm and cool is where this dog needs to be. You have broken his trust in you--so now ---walk the mile to earn it back! Talk to him in soothing tones---Never yell at this dog!! You have to make a lot of changes in yourself--to make them in him. A soothing, calm handling, soft voiced commands, and gentle play and encouragement! You will have to work hard with this dog to get him where he needs to be, if you love him you will take the time and work with him with patience and praise. His confidence has been undermined--build it up with play, and training!. If my dogs were afraid of anything (that will NOT hurt them), I clip on their leash and we explored it together. He gets LOADS of praise, and we faced every fear like this---together. He was a "baby lion" before he died, this past April. Your little dog needs reinforcement and encouragement, and soon his confidence will start to grow. A word of caution--go SLOW-- never force him--give him time to re adjust to whatever he is frightened of! If it takes two days to get there---take that time and do it right!