Press LB you will pull out a med kit, hold RT to heal him and LT to heal yourself. If you press LB twice you will pull out defibulators that is used to revive dead teammates while in combat, but you will have to have them charged up to 100% before reviving them, the more you use your med kit, the percentage on the bottom left will drop. Luckily it regenerates allowing you to use it as much as you want.
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They heal 21 Hp
There is no way to heal it unless you have a Splash Potion of Healing/Regeneration. Although there is a rumor that you can heal it by feeding it fish after you tame it.
Use a Paralyz heal or Full Heal. They are very cheap at PokeMarts.
No, it is considered a normal Pokemon battle. Does your poekmon heal every time you get to a trainer? no.
Dragonair can't heal HP, but it can heal status problems like burns or poison. yes, dratini also does ythe same thing