Accept your dislike for fiance's mother, then deal with it
Q: How do I tell my fiance that I don't like his mother? I'm sure he can tell, but I can't bring myself to say it out loud; she is very important to him and very involved in his life. However, she rubs me the wrong way. He doesn't understand when I ask him to keep certain things private. Every time he sees her he expects me to go along, too, which is weekly and way too much for me.
A: You tell him what bothers you about her and why — be specific, but not petty. If you don't know exactly why, try to figure it out before you say anything. And if you've tried but all you have is an unexplained gut reaction, then tell him that, too.
In other words, let the fact of your having to tell your fiance — soon, soon — inform the way you tell your fiance. You are keeping a potentially life-changing truth away from the person who's about to hitch his life to yours. Give him the information he needs, not by dropping a fait accompli on his lap, but by inviting him in on your thoughts in progress: your dislike, your fears of disappointing him, your impulse to protect your privacy, your efforts to honor his mother's importance to him. Introduce it as a problem you need his help to solve, because it is a problem, and you do need his help to solve it.
What you don't need is to flog yourself for your feelings, because to see them as "wrong" is the first step in denying them — and to deny your dislike for someone who is "very involved" in your fiance's life is to deny a runaway train. I suppose it's possible such a train could stop harmlessly on its own by swishing into the world's largest uninhabited shrubbery, but hoping for that is not the same thing as dealing with the problem. A disapproving DIL can be a good DIL if she and her husband work together to adapt; you're only a "mean DIL" if you sabotage, stonewall or lie.
'Maybe' to dinner invitation means stop asking about it
Q: I had dinner last week with a girl I previously dated, and we ended up getting together again later in the week for a movie. It was pretty platonic but we ended up talking about our relationship, and when I realized how much I enjoyed spending time with her, I asked if she wanted to get dinner again sometime. She said maybe and hasn't really given me a straight answer on it since.
I'm not sure what approach to take with that. On the one hand I would enjoy seeing her again, but on the other, "maybe" pretty much always means "no." What would you suggest?
A: "She hasn't really given me a straight answer on it since" pretty much always means you've been asking the question since — and that suggests you've asked more than once, since last week.
That is a pretty sure way to force a "maybe" into a "no."
If you have been pressuring her, then apologize for doing so, and then: "You know where to find me." As in, that's it, stop asking, the end. She will find you if she wants.