Hi, Carolyn: A friend is in a "relationship" with a married man who lives in another state but travels for his job. She met him when he was in our region for business. He no longer travels here, so a few times a year she will travel to meet him on his business trip, and they also talk multiple times a week. When they met, he said he was separated and waiting on this or that to divorce. Over two years later, no change. He still lives with and vacations with his wife. He has never spent his own dime to travel to see my friend.

My ex-husband cheated on me, as did hers. It makes me (and all her friends) sick to hear or talk about him. She brings him up more and more, saying ridiculous things that everyone else clearly sees as manipulation and lies.

I have already asked her what she expects out of this relationship and she will say "he needs to tell me what he wants to do." He has clearly told her with his actions he wants to remain married.

— Can't Deal With This Anymore

Can’t Deal With This Anymore: There isn’t a question here, so I’ll take that as my chance to answer however I want. Here’s a homemade Mad Lib for talking to your friend:

“Oh, _______ (proper name) — I know you’re _______ (adj) about this _______ (noun). You’re my _______ (adj) friend and I _______ (verb) you. But I can’t _______ (verb) you _______ (verb) yourself with this _______ (noun). Especially given both of our histories, it feels _______ (adj) to pretend this _______ (noun) isn’t a complete _______ (adj) _______ (noun). Please know, I am here for you and don’t judge you but will also not _______ (verb) this _______ (noun) anymore.”

I’m sad for all parties in this mess . . . well, almost. Compassion says you can hate the stupidity frailty and still love the friend. Say this to her if she’s unable or unwilling to see it.

Let me _______ (verb) how it _______ (verb).

Dear Carolyn: I've just started dating a widower of 10 years. His kids are grown and living independently now but were teens when their mother died of cancer. He and I have had three very comfortable dates covering some of our personal histories, careers, spiritual philosophies, hobbies, but he hasn't spoken of her illness, death, personality, etc.

I'm not clear whether I am supposed to ask gentle leading questions or ignore the subject completely until he opens up on his own. I'm not an experienced dater. I feel like there is an elephant in the room, but I recognize that I may just need to be more patient.

— Wondering

Wondering: When frozen by unbroken ice, talk about the ice itself — it’s an easier point of entry, and gives the other person an easier out. “I don’t know whether to mention your late wife or wait till you’re ready to.” Or, “I’m new to this, so that’s why I haven’t asked about your late wife — I’m following your lead.” Etc. He can then defer, deflect, open up or start a fine conversation about the challenges of conversation.

This applies to whatever “it” is you’re not addressing: Talk about talking about it. See where that leads.