If you have problem with entire group, likely problem is with you
Q: How do you know if you have good instincts when it comes to trusting people? I like to pride myself on that, and I'm sure I've been duped no more than the average person. But after a recent duping, I'm finding most romantic interests (or women in general, really) untrustworthy, and I back away. How do I know if I'm being paranoid or just ran into a bunch of shady romantic prospects?
A: Whenever you have trouble with all (group name here), it isn't about (group name here), it's about you. I've found this to be a useful self-diagnostic tool.
It applies when every boss at every job is a nightmare; when all other drivers are jerks; when all adherents to a belief are monsters, liars or fools. It applies even when there isn't just one group, but instead any group will do: "My teachers hate me," "Only the rich kids make the team," "I was never my parents' favorite."
So when you find "women in general" untrustworthy, that points to a problem with your instincts.
To identify the problem, please start with the whole "I like to pride myself on . . ." idea. What we hold up as our greatest strengths usually say more about our greatest vulnerabilities. Your taking great pride in your judgment of character suggests instead a preoccupying fear of betrayal.
A true strength, on the other hand, will be something you don't think about much; it's so reliable you can afford to take it for granted.
You say you've recently been duped, and you're reeling. This is a fine time to tease out your underlying feelings on trust. Specifically: Why is it so important to define yourself as a keen judge of people? Do you see skepticism as a mark of intelligence? And therefore believing lies as a personal failure? Are you worried about how you'll feel inside after being deceived, or how you'll appear to others?
You suggest in your letter, backhandedly, that believing a few whoppers is a fact of life. Maybe in that viewpoint you have the seeds for a different perspective on deceit: that believing lies isn't a personal failure, telling them is. Lying and paranoia are all about shifting blame to somebody else.
Believing, on the other hand, takes courage, and telling the truth takes courage. They're the two sides of taking a stand, of saying "This is who I am" — and knowing that stand might hurt. There's no shame in a courageous act, even when it turns out to have been the wrong choice.
Getting through to friend who makes poor dating choices
Q: I have a friend who dates married men all the time, yet feels frustrated that she can't find a "man of her own." What can I say to her when she wants to cry a river due to loneliness? I think it's a disgrace that she chooses men who are unavailable, however she doesn't see it my way at all.
A: How about: "Pretend you're a guy, meeting you for the first time. If you'd think you were a great catch, then keep doing what you're doing. If you wouldn't want you, then change whatever needs changing. Either way, it's not up to me."
Now, a rhetorical question: At what point is your taste in friends disgraceful?