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On the surface, my initial sympathies were with the LW and her boyfriend... however, I have to agree with Ken E., as well as other commenters, that there are too many unknowns in this story, in terms of the cultural expectations and the dynamics of the parties' relationships.
Worst possible scenario: the LW's parents-- and perhaps even the host-- do not believe the money was actually stolen, and for this reason the parents decided to repay the host. If so, then the LW's parents are obviously worried about this relationship and may be hoping it will end. If not, then the LW's boyfriend still has an incredibly difficult and uphill battle to win the parents' trust and acceptance, given their expectation that he repay a debt they accepted for him, without his knowledge, knowing that he would find it difficult under his current circumstances.
I can't think of a best-case scenario, since if the money really was stolen, and the father really did interfere (uninvited?) with the agreement reached by the boyfriend and the host, and still expects repayment... then the boyfriend still faces at least two dilemmas: to repay or not; to continue the relationship or not. And the LW really has very little power in the situation to influence a good outcome.
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Still, I also found myself wondering whether this incident actually happened as described, or if it is some kind of a "test" letter, for either Cary or his readers. You know, one of those sociological tests that tries to determine the ethical standards of a group of people...
Or, perhaps someone else wrote this particular column. It reads so unlike Cary, and not just because of the nature of the advice, but even more because of its style. Our beloved Cary, who writes so lyrically and metaphorically, and with such compassion, practically creating a personal myth for each LW... could he really have written this response?
Surely... Cary must have been influenced by the Ethicist at the New York Times, who admirably dispenses ethical advice, but would not be my first choice for a general advice columnist... Oh, wait, the LW's request was for some ethical advice, wasn't it?
After the 2004 election, while trying to reconcile a severe case of cognitive dissonance, I toyed around with my own alternate or shadow cabinet, but called it a Rotissurreality Cabinet.
Reading something that Ivins-- who is also one of my heroes-- had written on torture [http://www.freepress.org/columns/display/1/2004/1015], inspired me to nominate her [http://blogs.salon.com/0004000/2004/12/05.html#a143] to head up the EPA.
After all, she had also written so poignantly in her books on the damage done to environmental issues by this administration with its Orwellian use of language to disguise its true intentions.
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If Quakers could influence the DNC, there would be a nominating committee, whose charge would be to come up with a list of qualified and willing candidates. In an ideal world, Molly Ivins would be its clerk (Quaker for chair).
So much for fantasy...
This is one of those situations where I think gender is really important. In general (emphasis on "in general") young men default to career and new adventures, and young women to relationships and those things that are already known to them. Stretching your comfort zone just a bit means doing the other thing.
For a 20-something woman, that means giving yourself more time to develop more self-confidence about your ability to survive in the city is something you can afford now (what Cary says about those difficulties is true), but probably would not be able to do later on, if you established a more permanent relationship with the boy back home. (If it were me, I probably would not have wanted my mother to come live with me. However, if my daughter faced a similar choice, she would likely have me come stay with her until she feel better situated.)
Also, you didn't mention exactly why he cannot drive a car, but possibly, this condition might also make greater demands upon you than is customary for someone in her 20's. Don't let taking care of the boy back home be what keeps you from learning to take care of yourself in all the very best ways that you can. It is still true, even in 2006, that a woman is more more likely than a man to give up some of her potential in order to maintain a relationship, or get married, or have a baby, instead of testing her ability to achieve something in the world.
Whether you can have it all, or have to choose what's most important, is still under debate. However, I think most people would agree that the order in which you choose things can either minimize or maximize the range of choices left to you. It would be easier to leave Chicago and return to the relationship and a suburban life if your present situation does not work out, than it would be to establish a suburban life and then try to transplant it to Chicago.
Like wheat and corn... spouses, kids, mortgages, dogs, etc. will all take what they need.