At a tough spot career-wise... not sure what to do

Probably true but even six or nine months is still nothing compared to waiting nine months to get into school, go to school for a year, THEN look for jobs again all the while still making barely enough to pay rent. I currently live in my parent's house so I'm not completely broke all the time but I'm starting to feel like a loser, I can't stand it. It's pretty embarrassing to go on dates with girls and have to admit sooner or later I live at my parents' house with my mom and 2 younger brothers,

Nothing comes easy. Sounds like you thought you'd be able to snap your fingers and choose which job offer paid the most $$ shortly after graduating. Rarely can one walk into a dream job fresh out of school without spending some time in the trenches. Going into the debt hole more by getting your Masters probably isn't the best idea either. Depending on how reputable the graduate school is, having a very little experience for the group/team work projects in is going to make it more difficult. Having 22 to 28 year olds with little experience but think they are 'know it alls' in graduate school is frustrating for the 30+ year olds who actually have real world experience who also know they don't 'know it all'. If you do get your Masters, you will then complain that you are over qualified for all the entry level jobs that 24 to 26 year olds are applying for yet you won't get the jobs for folks who have 5 to 10 yrs experience since you don't have the experience.

That crop duster gig isn't so simple because if it were, everyone would be a crop duster pilot. As another pilot has already pointed out, the investment to get your ppl and then commercial license will put you in the poor house pretty quickly. Then you'll have to work in the middle of nowhere as a pilot since the pilots with experience will be flying in the desirable places.

As for the girls you go on dates with now, if you think you need a good job or a place of your own to get respect/credibility, then you need to work on your confidence. They shouldn't like you for what/where you are/have but they should like you for you instead (ie: personality/character).