Find out what your maintenance intake is and eat over that a day. That will enable you to put on muscle easier. You will gain some fat but thats ok because once you have gained enough muscle you'll...
There is also this thing we like to call "common sense". It can usually answer very simple questions such as this. My common sense is telling why OP is in the red.
Side question, will they take OP in the military? Sounds like it may be to risky for them to do it as he could easily become a hindrance to the team if his knee busts up in the middle of a fight and...
Seriously, do something with the two of you. Not dinner and a movie. Girls hate generic bs. Figure out something fun that she doesn't do often if at all as long as you think she'll like it.