I’ve been dating a married man for just over a year. We met through work and instantly hit it off. I’m totally in love with him. But when I thought, after six months, that I couldn't take the situation anymore, I tried to end it, thinking he’d never leave his wife (and having never asked him to, because I assumed the relationship would then be null and void).  
He confessed that he never brought it up because he thought I didn't want a serious boyfriend. We agree that we both wanted each other and that things would change. Six months later, things are still the same. I hear that it’s going to happen, but I'm terrified to ask for answers because I don't want to pressure him. And frankly, I'm not sure I want to hear the answer.
I'm willing to put my life on hold for him but I need some timelines. Is that wrong? He’s an amazing man – kind, funny, and there’s no one I trust more. But I’m afraid I'm not seeing something that EVERYONE else is seeing, about this relationship. Will this ever work?
- Frustrated

Here’s what everyone else can see clearly: he’s neither kind, funny, nor trustworthy when it comes to dealing with his family; the longer he prolongs the affair, the longer he’s more a cheater than Mr. Wonderful.
Yes, some affairs do work out … but only if the married person faces up to the fact that he/she has obviously been unhappy enough in the marriage to want to stray, and needs to make a clean and responsible break (equitable division of property plus child support, etc.). It’s also the only way the next relationship can proceed with some decency and the crucial caring about the welfare of his first family.
No, so far, this scenario – his lack of communication with you about what he’s thinking and doing or not doing about the situation – doesn’t look like one that’ll ever “work” for you.

I’ve long known that I sabotage my relationships, and recently cost myself a five-year relationship. He has his short-comings but we were both mostly able to look beyond each other’s imperfections.
However, I lost his trust twice before; this time there's no chance we’ll work it out. What is it that drives people like me to always completely ruin anything positive that happens in my life? I’ve seen a therapist about this and don’t believe that going back will help.
- Destructive

Therapy certainly can’t help those who negate it from the start. All you’ve learned is the lingo – sabotage. But maybe you didn’t hear nor want to explore reasons why you possibly feel you don’t deserve happiness, or you have to test people till they can’t take it anymore.
I urge you to take a fresh look at your earliest relationships, where you’re most likely to have learned to respond to close people this way … with no trust on your part.

I’m 20 and don’t have a girlfriend. How can I get one?
- No Idea

Practice. Focus on your friendships (NOT romance) with females you already know through school/work/neighbours, etc. Get to know them better and feel relaxed in their company.
Be open about wanting to “practice” your social skills so you can find it easier to chat up potential girlfriends. Most women friends would be happy to help. Get confidence first and then finding a girlfriend will come naturally.

When I recently gave birth, I left a message with my boss of the birth announcement. I didn’t get a call, email or any type of congratulations. Is it because she’s the boss that she doesn't have to? I also left a message with our one major client and the same thing occurred. No congratulations. Is there new-baby etiquette?
- Curious

Most etiquette of this kind is a combination of common sense, sensitivity and good taste. The normal response to a baby’s birth is, of course, congratulations … whether from a boss, client, or the dry cleaner you frequent.
Babies are a blessing meant to be welcomed into the world, especially by those who are part of yours. But these people may be thoughtfully giving you time to adjust, before calling. Also, good taste calls for more than a voice-mail message, when possible, so eventually send out baby announcements (or e-cards) and they’ll likely respond.