My boyfriend of four years and I are both 40s and child free. He’s never been married; I’m divorced and own my home. He stays with me though he officially lives with his parents and has never owned property.      
      He treats me really well, helps around the house and is generally sweet and kind, but we have no meaningful conversations.     
      I completed college; he didn’t. I read a lot and take courses regularly; he does neither. We never discuss feelings, the relationship or anything weighty, but spend time together as companions/roommates and take care of our beloved dog.     
      He gets aggravated if I try to talk about anything personal. I have many hobbies and goals such as world travel, further education, home improvement and investing; he does not.     
      I also feel sex is important, but he has many inhibitions and the sex is unsatisfying for me.    
      It’s basically just companionship, but every man I’ve ever loved who satisfied my desires, ends up leaving. Should I just be happy with what I have, keep looking or give up and remain alone?
      - Confused

Here’s one personal topic he’s sure to discuss: Joint custody of the dog. It’s time for you to move on. You’ve been accommodating to something that doesn’t feel right, fearing you can’t do better. It’s an unfair way to deal with this man, or yourself.    
      Change the set-up: He stays at his place and you see each other only periodically, only as pals. Meanwhile, you get personal counselling.       
      You need to shuck your defeatist attitude about finding love, and examine your own choices of previous men who didn’t stick around.
      You may be more educated and progressive than this man, but that attitude about him is part of the problem. Stop settling for less than what you both deserve - someone to share real happiness with you, and someone to really respect him.

I’m a high school girl who travelled to visit my brother and his new wife. She’s nice, adores my brother, but tends to get very serious and emotional.   
      I’m 30 pounds overweight which has hindered my self-esteem, especially coming from a family of health nuts. She immediately began complimenting me on my other features before suggesting I lose weight.    
      She talked about my weight in front of her friends (strangers to me) and began weeping. Every time I ordered a soda or glanced at a french fry, she’d sigh loudly.       
      I appreciate that she’s concerned, but find it humiliating, awkward and offensive, especially since we’ve only just met. I spoke to my brother about it. He shrugged it off and told me to loosen up, and maybe take her advice.     
      I want us to have a good relationship, but she gets genuinely scared and anxious for me whenever the topic of food or obesity comes up. What should I say to her?
      - Upset

Say thanks, but no thanks. Yes, she’s shown great concern and you can start as diplomatically as she did by saying you appreciate her caring.  
      Then remind her that all teenagers, as she once was, do better with support and encouragement rather than constant reminders of their sensitive areas.     
      If you want to tackle your weight issue then tell her you’re willing to learn, privately, about better nutritional choices and will try to practice them when you’re ready to do so.    
      If she continues to cry and embarrass you in public, end the visit as soon and as pleasantly as you can.

My high school best friend has changed: he got jealous fast and depressed. I once went out with his girlfriend (as friends) and he lost it. For 10 years afterward, he brought it up. At a recent guys’ get-together, he rambled on about his failed relationships.   
      I listen to him vent, but he doesn't take my advice. He’s bored and depressed and depresses friends when we talk to him. I want to remain his best friend, or has that ship sailed?
      - Curious

This is about his mental health, not the friendship. He needs more than buddy chat, because something’s affecting his moods beyond what your advice can solve.
      If you value the best-friend connection, step up to a more serious task and try to convince him to see his doctor.
      Accompany him there. He needs to discover whether he needs therapy, other treatment, or has a health problem debilitating him.