LW#1: LOL. This is so hilariously fake. "Dear Prudie, I seriously have an enormous wangdoodle, and my wife can't shut up to her bffs about how awesome it is."

Yeah dude, seriously.

But in the interest of playing along. Q #1: How old is this wife? Q #2: Why do you even let her respond with "it's your best feature, and I have to let people know it?" Because at that point, you should just say No. "No, honey, I don't care how awesome a feature it is. It is my business, not my personality. That is all. Don't talk about it." Q #3: Telling chicks she just met? Oy. There is a maturity issue here.

Anyway, the only way to get her to stop is to quit letting her make excuses. This is private info, and you have a right to keep it private, and she, at some level, knows this but really likes trouncing your boundaries. Erect (hee hee) better fences.

LW#2: Who can understand the mind of a three year old?

Maybe you should take him to the store and ask him to help you pick out a suitable jacket, because he needs to stay warm on cold days. It could be worth the $$$. Actually, I've seen jackets for $$ and $ lately. But really, what cost non-fit-throwing weekday mornings?

I'm sure I'll be the millionth Frayster to say this, too, but here goes: This sort of inflexibility might herald some sort of autism spectrum disorder. But if it's only the jacket, this may just be his thing. I refused to wear a rust-colored down jacket when I was a kid because I thought it was ugly. Of course, I was in elementary school and could express that verbally.

LW#3: Well, if you go along with this guy's lies, that's not exactly walking in truth, which is the fundamental requirement for a functional (much less healthy, rewarding and positive) relationship.

What do you mean, "he's not the guy I thought he was?" Do you mean rich? Community-oriented? Nice? Loving? Competant with money? Or just honest about his fiscal position? I'm a little tweaked by this phrase of yours. Money management skills do often reflect certain aspects of a person's character and people's interrelationships, but I'm not sure what you mean here. You might want to reflect on that.

I'm going to advise you to not listen to your mother. You had an education, you're an adult, and while you can totally ditch your parents, they don't seem to have raised you poorly or neglected you. At the same time, I'm going to advise you to listen, as in doing an act of love, to your mother. You probably don't have the fiscal resources at this point to "save" your parents, but you may be able to give them perspectives on how to get over the hump.

Also, maybe you should encourage your dad to get mentally evaluated. There might be more going on here than you think.

You have a very complex problem laid out in front of you. It's hard to give advice other than the sort that encourages you to get all the family "secrets" about money out on the table to plan an attack on the problems that have led your parents to this place. The shame and secrecy have contributed to their poverty, they won't help them get back on their feet.

LW#4: Oh, I once dated for too long a guy who was boring, not too smart and basically a loser because his mother was The Bomb.

While I would say, sure, stay in contact if you want, you have to consider that she may not appreciate it, and if she does, her son might not appreciate it nor his future girlfriend.

But, hey, right now we're talking an email of appreciation that gives the mom closure if she wants it, an opening if that's her choice. How much damage can that do?