Dear Eric: My youngest son (my baby!) had a horrible breakup last year. I still hate her and sob-yelled during an Alanis Morrissette concert to “You Oughta Know.” Yes, I sob-yelled in public. Cue shame. And righteousness. Hate is powerful. Said son is adorable, nice, has a great job that he loves, etc. Yet, he won’t date.

Let’s be clear. I need grandchildren from this boy. He’s the best one of the bunch (don’t tell the others). How do I encourage him to get out there without actually saying those words? Or do I just adopt more cats as my grandchildren?

— Morose Mom

Dear Mom: Cats. As I vividly recall from the Morrissette-fueled sob-yell periods of my youth, the chorus of “You Oughta Know” includes the line “I’m here to remind you of the mess you left when you went away.” Alanis would no doubt remind us that getting over any breakup, particularly a horrible one, can be a long, grueling experience.

There’s a rule of thumb that posits it takes half the length of a relationship to get over the end of said relationship. But don’t go running to your calendar to circle some due date in your son’s future. His mileage will vary.

This process is his own to create and he is currently taking the time he needs to heal. You know how hard it was for you to get over the breakup — indeed, it seems like you’re still working through it — so imagine what a mess he’s left cleaning up in his own heart and psyche. The last thing you want is for him to jump into a rebound relationship and start having babies.

You clearly have a lot of compassion for your son, which is wonderful. But be careful not to slide into codependent tendencies. The breakup may hurt you but it’s still his breakup. Tread carefully and keep your comments in the supportive, rather than prescriptive, range. No mom wants to see their child go through heartbreak, but you’re not going to help him gain the emotional strength needed to jump back into the dating pool by pressuring him.

Dear Eric: I am 67 years old and have kept a daily diary since I was 15. I grew up in the ’70s and things were, shall we say, a little crazy (sex, drugs and rock ‘n’ roll, as experienced by a woman who went to a parochial school and wasn’t exactly a model of obedience). Times were different.

Now, I wonder what to do with all of these volumes of my life. I’m married, but we have no children and no relatives that I would even remotely consider entrusting the good, bad and ugly of my/our lives to. I feel as though they have historical meaning, perhaps significant to some entity, but finding that entity has been problematic. Any suggestions?

It has become such an ingrained part of my life to write every day that I would find it difficult to just stop, but if all of them are destined to end up in a landfill somewhere, I might have to make some hard choices. Incidentally, I’m seriously optimistic that I have at least a couple more decades of diaries left to write, if I do continue.