...In which Schuyler The Cat (fresh out of rehab!) luxuriates in another round of self-indulgent, egoist, manipulative masturbation in the guise of self-help, all the better to feel he's done a good thing (if only for himself, he is selfish, you see), although it gets scarier and scarier that he refers to himself in second-person narration. Jesus, what's next...
*****
Someone Else's Child - you said: "What would be a graceful way to approach this family, who has never known of my existence?"
A real human being might try using a fucking telephone, asswipe. God, I have to do everything around here. I mean, do you have to do this? Really-really have to? Okay - then do it. It sounds like you fear if you and the "others" are all in one place together at the same time you'll reach some form of bizarre id-driven emotional critical mass and explode into gobbets of organic goo. Listen carefully: you won't, okay? Call. Now. Feel better?
Oh, and by the way: this may not be pleasant for them, Okay? Keep that in fresh in your mind, while Pandora's Box creaks slowly open to reveal...you.
*****
Out and Stuck - You said "How do I tell him that for the last two years I have been in a relationship that our parents want him to know nothing about without creating a rift between him and my folks?"
Sounds like you don't. Welcome to the human race, when men are men and women are women and all are equally as fettered and foible as they are sickeningly entitled to it. You know, I heard somewhere that ( in the REAL world, not here, in Prudie's fantasy land) gay folks are not widely appreciated in some circles. Did you ever hear that? Wait - you're a lesbian. Of COURSE you've heard that! So pick your battles, and pick them wisely. Never mind you should be well beyond these sort of surprises at this point in your life, I would think, that's incidental to the fabricated histrionics of this letter.
You shouldn't be asking for graceful ways to come out of the closet that's been standing wide open for so long, lovergirl. You should be enjoying your girlfriend and asking yourself "why the hell is this still an issue?"
*****
All But Dissertation - You said: "Am I being petty, or is he being pretentious?"
Yes/yes. Shut the fuck up. Pass same advice to him. You are both living proof that the term "Graduate Students" can include Rain Main and Forrest Goddamn Gump.
*****
Haven't forgotten - you said: "Should I tell his family?"
No! I think you should write a goddamn book about it, then sell that to some schmuck in Hollywood and get a movie deal! That will make all this bilious, frantically overdone bullshit FAR more melodramatic than it already is! Scene I: The boyhood frolicking! The sweet music denoting your happy, newly carefree life, healing the wounds inflicted by cold and distant parents where you once wasted away at the stony, lifeless boarding school! Then, dark clouds, ominous tones! The fiery crash!!! Ka-BOOOM, and then soft strings build as you fade to (Scene II) the funeral, graveside, tears streaming down your face as you look at the coffin and sputter "but he was only 18 years old! Why, oh why did this have to happen?" Scene III: Cut to the schoolyard, the memorial plaque embedded in the ground stating "Dedicated to Jimmy - the greatest and swellest pal a guy ever had, though he seemed a rather mediocre pilot."
Scene IV: Years later, you, struggling to accept the fact that, yes, you are a fucking little girl in a man's body, all teary eyed and burdened with the weight of knowing that your bestest buddy and good pal Jimmy is gone, that you don't deserve anything good ever to happen to you because he died and you didn't and you have this...hole in you, this dreadful gap in your existence.
Then let's just cut to the scene where the psychiatrist says "fuck, dude - when are you EVER gonna grow up? Sorry about Jimmy, all that, but, I mean, really, what the fuck? Get a goddamn life! And wait...Jimmy was HOW old, Prudie?"
And the music swells as the truth dawns on you: while you have been scarred by such tragedy and such pain, that life truly, truly goes on, that you are here for a better purpose than moping and being a childish dramatic asshole, and your life has more meaning than all that, and...
Wait. What the hell am I talking about? Cut that last scene: You haven't realized that at all, have you? Maybe just rewrite that part to say you'll die missing Jimmy horribly and evermore, you'll never get over it, because you need that to exist in your heightened state of hyperbolic, overwrought, dramatic, pathetic angst, all the better to Peter Pan your way out of acceptance of your own "late 30's" (albeit successful) existence.
Look - sorry about Jimmy. I buried a lot of friends back in school (although none so cleverly...fabricated as him), and it really sucked a lot. Now get over yourself and grow up.
Next: if you're going to go lay your fucked-up trip on his family, I might recommend: don't. They don't need your drama.
...And now, my friends, we cross back over into the world of the real, where the phone is ringing and meetings are waiting, and my coffee got cold, and it's my wife's birthday and I STILL don't have a clue what to get her; and yet I will go on! I will survive the tragedy of frigid java and a wife bearing no evidence of a gift, all the more I should, as I can aspire to other, greater things; and even now I gain strength and succor from knowing that I - just a plain and simple man thinking always of his cute and wonderful bride and saddled with a thankless, rough cup full of cold coffee - will never, EVER be as fucked up (invented as they are) as these folks. Fade to black...