I’m 47, he’s 38 and we’ve been dating for five years after my divorce. He lives in another city and spends weekends at my place. He helps support his parents and is of a different ethnic background.      
      I’ve occasionally tried to break up with him, but he insists that he loves me and only wants to be with me. Incidents:      
      1) At a party for his sister's birthday, he flirted with the waitress in his language, and asked his sister, publicly, to drop me off so he could be with the waitress.    
      2) His boss called me to say that my partner had just spent an hour in the bathroom with a female co-worker. My partner said it was a joke and not true.     
      3) I checked his cell phone (only once, on a hunch) – he’d called an erotic massage parlour. We entered couples’ therapy, where he gave excuses about “only making jokes” for everything.      
      Since then, he’s attempted to regain my trust. But I feel sad because he can't be open about why he does these things. I love him deeply but have little self-esteem left.
      - Dejected

You may’ve been afraid to play The Older (wiser) Woman, but since his behaviour is sometimes childish and insensitive, you need to set some boundaries.     
      Pranks are for those who find being set-up funny, while in your case, it’s humiliating, especially when others are involved. Then, set a timeline for The Talk: If he wants to be with you, what’s the plan –living together in one city, marriage or other formal commitment?    
      It’s your insecurity in the current arrangement that has you depleting your own confidence, instead of insisting on respect and a clear understanding about the future. Speak up.

I’m holding my mother-in-law’s 90th birthday party at my daughter’s house (larger than mine). She’s recovering from severe postpartum depression, but some anxiety still remains and she doesn’t want strangers in her house.      
      Yet my sister-in-law (the only daughter) keeps inviting her friends and even ex-neighbours! She originally put two friends whom I had rejected back on the list, and has since been inviting friends and telling me later.    
      My daughter’s considering cancelling the party but we don't want to disappoint my mother-in-law.  
      - Bad Feelings

The problem is the original plan as much as your sister-in-law. Someone recovering from severe depression and still anxious doesn’t need this stress!    
      If you move the party to a restaurant and have everyone pay for their own guests, your SIL will swiftly re-think her list and the changed circumstance will provide a perfect excuse.    
      But as for your in-law relationship, consider this: she’s the only daughter, yet you set all the rules even to rejecting her guest suggestions. So she invited more.     
      That’s a two-way relationship problem with both of you contributing. Look for solutions instead of blame.

I’m in my mid-50s, educated in Early Childhood Education, taking extra courses (Personal Support Worker) because I cannot find a full-time position in my field. I working for an agency and its slow for them also.    
      I’ve placed ads in the city and community newspapers and handed out flyers personally. What else can I do?
      - Worried

Experts say that finding full-time employment can take at least six months. You’re on the right track by expanding your field; consider other skills you need to update, e.g. computer use, interpersonal communication, etc.    
      See a career counsellor through your education facility or a social service agency for more detailed help.

My wife of 30 years can no longer enjoy intercourse – intolerable, immediate pain at the entry point. She’s willing to satisfy me in other ways but I don’t have much interest in that.    
      Her two doctors say this is common in post-menopausal women; she’s 55. She says my refusal and disinterest is now my problem.    
      Due to past conditions she cannot take estrogen or other hormone medications. Lubricants haven’t worked. We do have a loving, caring relationship, together forever.
      - Frustrated

Boost both her efforts and your efforts. For her part, she should be seeking more information from a specialist, e.g. what’s causing the pain and whether a minor surgical procedure would help.    
      For your part, in a loving relationship of 30 years, when one partner requires an adjustment, it’s not good enough to say, “not interested.” Explore, enjoy and appreciate your wife’s offer to satisfy you sexually.