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I'm not sure of the logic that equates graduate student with trust fund baby. Perhaps that is true in some cases, but most of the graduate students I know and have known are or were not independently wealth. In fact, they usually struggle to feed themselves and make the rent.
I laugh openly at the idea that military service would be good for anyone. The only thing I see in returning veterans is a deference for authority, a lack of real world job experience, drinking/drug problems, and difficulty fitting into normal society. Military service is perhaps noble, but its no fix for what ails most young people, a lack of genuine direction and purpose. Remember, the goal of military training is to make the enlisted willing and able to kill and be killed. Nothing more, nothing less.
On the other hand, the LW certainly does seem very immature and self-centered. My advice is to her that you should dump both guys, go to graduate school, and do some foreign service. The experience will do you some good. Also, both of these men seem like losers. Being intelligent is mostly genetic. What matters is what you do with your mind, what you achieve. All three of you seem to be moving sideways, not forward. Get off your butt and accomplish something meaningful.