As you all know, original letters are here.
LW#1: There are a lot of red flags on this play. You read a lot of self-help books, and yet you realize that you're a controlling, judgmental, unloving, abusive creep when you're in a relationship. You want to change, obviously. And I bet you've been flamed to kingdom come by all the right people.
Well, this is a serious problem so I have two tips from you. Number one, get a shrink. Seriously. Like NOW. There should be one on campus, if not some sort of referral service that can help you find a cheap or no-cost alternative.
Number two: Read up on feminism. I swear to God, this is a framework that will lift so many scales from your eyes your mind will blow up. At its bottom, feminism says that women are people, too. Women who are allowed to have the failings you yourself work so hard not to have (like occasional casual sex -- where no one gets hurt -- is a bad thing? Come on, dude!). Women whose worth is not measured solely by their conformity to your ideas of what they should be, but by the profoundness of who they actually are. Women who have histories that you don't have to know because you can know the personality that has sprung from those histories, and cherish that personality.
A special note on jealousy: You need to let the idea that a woman is tainted by her previous relationships go, because guess what? She did not belong to those men and she does not currently belong to you. You have nothing to be jealous of, because she as a person is not yours. You should consider yourself two people who are lucky enough to have the time you have together. Because really, all you have in this world is time, your brain, your body. And that's it.
I'm also totally freaked out by your feeling that you and your girlfriend have to be perfect in all ways. I know you're young, but you're a human being, and as such, you have failings. Denial of your personal failings leads to some really awful, wacked-out behavior that is actually always way way worse than those human failings.
Anyway, get thee to a shrink. A feminist one, at that. And for the love of little baby tree frogs stop doing this ridiculous "we fell in love like superfast" without recognizing that those dopamine drops and instantaneous attractions are clear and present warning signs that you're about to fall into old, destructive patterns.
Special to Orbiters: Isn't it interesting that the inverse of "He's great but he wants me to drop 20 pounds and all contact with my family" is "She's great but she had teh secks before she met me and for reasons of which I disapprove even though I was not a partner to said secks"? That is, that it all boils down to the same problem but from two different perspectives?
LW#2: Hon, you don't owe Ted anything.
That was your mother's money to spend (so to speak), and so she did.
Sounds to me like Ted could use a little tough love from Michelle Singletary (and really, who ARE these people who think a job that requires, max, a high school degree can support a family? What are they smoking? Why do so many Americans totally fail to recognize that the dream of a working father, SAHM and 2.5 kids has only been a reality for a very small group of people for any significant time at all? That it is not a birthright, either?). She would totally call him out for being triflin'.
I would withhold any hush money. Otherwise he'll just become a whiny pain every time he needs something, but to you instead of your parents.
Also, send him a copy of the letter.
The thing you do owe someone is a break, for yourself! You have done everything right, and against the odds. So pay down your mortgage/put a down payment on a home, put some away for college for the kids and use the rest to get that new appliance you need and save for the car repair bills you know are coming eventually.
LW#3: This is a crazy, crazy lady. Just give her a hairy eyeball and walk on.
Look at it this way: She isn't going to stop burning bridges with just you. Eventually, she'll have to go to a whole new neighborhood to wreak her special crazy havoc.
LW#4: Unfriend her. Duh.