What should a girl do when her "boyfriend" and her are in an "awkward spot in the relationship??

All you gotta do is talk to him. It is the only way round it but you have to be mature about talking to him so you's both get things sorted out or it won't work. You say he doesn't do the whole confrontation or sharing feelings well you just have to take it lightly, don't come on too strong with talking about loads of things just bring one thing up at a time in a normal conversation, then maybe day or so later bring something else up. You's can work through it