› firstname.lastname@example.org 
I'm a 50-year-old man who has gone without sex for too long now. To me, my ex-wife's 35-year-old niece is the true personification of the "MILF." She's had her two kids, got divorced, and still looks as hot as she did at 18, when I first developed an incredibly deep infatuation. Since I was still married to her aunt, I couldn't indicate this in any way. Now I can't stop thinking about her. I know it's holding me back from pursuing other opportunities, but I've found that I really need her ... bad! I guess my questions are, how appropriate would it be for me to make my thoughts and overwhelming feelings known to her? If appropriate, how should I approach this? I don't want to freak her out, but how should I tell her that I've had the hots for her for 17 years now and would do anything to go to bed with her at least once?
Not Really Her Uncle!
We'll get to your questions, but first, "... the true personification of the ‘MILF’”? She “still looks as hot as she did at 18"? Can we talk about this? I know that new parents are notorious one-note bores and I swear I'm not one and will keep writing about other topics, but while I've got you, this MILF business has got to go. First off, nobody looks as good as they did at 18 (and frankly, we could all live without the pressure) and second, what does it even mean, "MILF”? By specifying the "mother" in "mother I'd like to fuck," does the speaker intend to make a distinction between the rare mother worth fucking and the unfuckable masses? Or is it really the "mother" part that intrigues, that sexy whiff of fecundity, that milkshake that brings all the boys to our yard? My personal suspicion is that it's the latter masquerading as the former, that the fascination with the pregnant or baby-toting Heidi Klum or Angelina Jolie is not fueled so much by the fact that they still look "hot" as by the implication that if somebody knocked them up, then so, by extension, could you. But I may be getting a little theory-addled here.
I bring all this up not so much out of a wish to render my readers walleyed with boredom, but because I was so touched by a new blog called "Shape of a Mother" (shapeofamother.blogspot.com) that I'd take pretty much any opportunity to mention it, even in a column about wanting to fuck your ex-niece-in-law (which, by the way, whatever). The concept is elegantly simple: have a baby or have had a baby or in a few cases don't have had a baby, take a picture of your transformed body, write a few notes about how you feel about the changes, and Bonnie, the blogger, will post it. The result is an extraordinarily moving document, whether you see it as political (I surely do) or as mere documentation or even as art. It reminds me, in a gut-punch way — not a "wasn't feminism fun?" way — that sisterhood not only was but can still be powerful. Also, when my absolute best self is not in ascendance, that my own recently ravaged body is not really so ravaged, comparatively. In your faces, stretch-marked bitchez, I got off easy!
No, seriously, this sort of normalization by exposure — see Joanie Blank's pussy-picture book, Femalia, for a similar and similarly successful tool for fostering self-respect and even self-love among women who may have been feeling freakish, ugly, and ashamed of their perfectly normal bodies — works. It may be the only thing that does work, and it's way cheaper than therapy. All it takes is seeing unretouched women (two- or three-dimensional, either way) who don't have a modeling contract or sex with Brad Pitt. It works on men too, although men as a group seem less inclined toward this sort of collective feel-betterism. They can still be cured of a lifetime of self-loathing by mere exposure to the unglamorized truth (it's five and a half to six and a half inches, dudes).
Let's get down to it: this woman is not your relative, your ex-wife is not your wife, and nobody cares. Oh, and she doesn't want to fuck you, so it's time to give it up already.
What you have here is not a crush or a fancy but something verging on obsession and by definition unhealthy. If you insist on trying to get somewhere with her, you should really leave out the part about thinking dirty thoughts about her since she was 18. That's pretty skeevy, pops. If I were her, I'd change the locks.
Ask her out, decently. Emphasize interest over obsession. Try not to sound like you have a secret room in the basement plastered with her photographs, and then take no for an answer. We can only hope that her rejection breaks the spell. She isn't the one holding you back, you know.