He’s been my best friend for 10 years - we never dated nor had romantic interest in each other - but I love spending time with him, his parents and his extended family. However, while he’s now dating an exceptionally nice woman who makes him happy, and I want him to be happy, yet I feel I want to cry.      
      I think I’m jealous but don't understand why. He took her to an event we’ve attended together for eight years. I was hurt, but didn’t let on. How do I get over these feelings?
      - Saddened

It’s the end of an era; now, embrace the beginning of another. Do not make the mistake of seeing his girlfriend as competition, or else she’ll feel that vibe and consider you the same way. The quantity of your time together will change, but the quality of a great friendship can be maintained if you welcome her, too.       
      Your sadness is natural … but only if temporary. Otherwise you risk pushing him away. Consider that you two leaned on each other partly due to the absence of romantic partners. So now you can also, like him, be more open to finding your own lasting partner. For next year’s “special event,” invite them for a get-together beforehand, and suggest you attend as a group.

My mother-in-law of four years was rude and abusive to me days before our wedding. Since then we don’t speak to each other. My husband’s been supporting her since her late-50’s, (she’s 63) with no reason for her to stop working, other than she says he MUST take care of her.     
      He pays her mortgage, fees, bills, food, everything. She lived with us for over two years after the marriage, and abused me several times. She checked our room when I was out; we had to lock our door. She divorced when her son was a baby and is jealous of our happiness.
      When our two children were born, she offered no gift or help. When she moved out I didn’t allow my husband to bring the babies there (they were two-months-old) but agreed she could visit them here, though she still won’t speak with me.      
      Also, whatever we do, she demands the same, e.g. when we bought our house, he had to buy her a condo. If we go on a holiday, she must go, too. I love my husband but cannot understand why he doesn’t keep her away from our family and kids. That’s all that I want. It’s his business if he’ll support her.
      - Losing Patience

The important relationship here is between you and your husband; but to protect and preserve it, you need to have some compassion for your mother-in-law, as difficult as she is, or Hubby will lose respect for you.     
      Her fear of losing him has perversely caused her to behave badly with you. You, by contrast, show a reasonable side by understanding his financial support for her. But it’s not reasonable to think your husband can keep her away from his family, UNLESS her abuse has been physical.    
      Otherwise, he must tell her that she must speak to you when in your home. Then, you two need to draw some boundaries, but also agree on inclusions. Example: You need some vacations without her and he can also pay for her to get away without you, if he chooses. If she becomes a more pleasant grandmother presence, you can then take her along on a family trip.

I’m a gay girl, wanting to date my “straight” roomie. That’s in quotes because she’s always been with men, but we’ve had a few intimate adventures. We were just having fun, it’s been awhile, but I’ve been wanting more.    
      I’ve made minor moves, I’ve also commented about our adventures but her responses have been neutral and confusing. She never completely ends the idea. I don't want to come on strong in case I’m wrong and it hurts our friendship.
      - How To Handle?

Treat your roomie as just that. If she wanted more, she’d have let you know … your “minor moves” and comments have been hints that she wouldn’t miss getting. Just like you, she doesn’t want to risk the friendship, or the convenience of your current housing situation.    
      And as a thoughtful person, she doesn’t want to insult or reject you. Lots of straight people have occasionally experimented with “adventures.”