Adapted from a recent online discussion.

Question: My friend Emily dated Andy a few years ago. They broke up spectacularly. Emily has always said Andy was the most controlling and insecure boyfriend she has ever had, which always surprised me because that does not come across at all when I interact with him.

Andy and I have gotten close over the years and have recently been on a few dates. Emily has totally moved on and is fine with it, but it really bugs me that I feel like I'm waiting for these negative traits to suddenly appear. Is this something I should talk to him about, or do I just discount Emily's opinion until given a reason to do otherwise?

Answer: Seems to me there's a lot Emily can say that will be useful to you. For example, did she see these traits in Andy early, or did they emerge as things got serious? Were there signs she didn't recognize at the time but that his later behavior explained? Were there specific triggers? Dig a bit to see if they had mismatch issues vs. an Andy-is-bad issue.

Also, how reliable is Emily as a judge of character?

I realize some people might recoil at such kiss-and-tell recon, but "controlling and insecure" is serious stuff. Yes, you have your eyes open, that's good, but borrowing a map would just be smart.

As for talking to Andy about it, I don't think you blurt, "Emily said this and I'm wondering if it's true." That could make Andy both defensive and unwilling to look inward. Better to talk about life, love, and hypotheticals, and see who both of you reveal yourselves to be. In particular, listen to the way he talks about his exes. Are they all crazy? Is everything their fault? And, in general, is he a blamer, a perfectionist, a person of strong preferences?

Question: My housemate and dear friend just got very bad news about his mother - cancer returning, this time advanced.

I've been following his lead in terms of bringing it up, etc. What, in your own experience, was most helpful? I don't want to ignore it or make it dominate our conversation, and don't want to make a "sympathy face" all the time. Any thoughts?

Answer: What a good friend your housemate has.

You can be really helpful by just absorbing some day-to-day hassles. Cover some of his chores, grocery shop for two versus one, add an errand of his to your list.

You can also offer distractions, since those can be just as useful as sympathy, depending on his need. Get used to the phrasing "I'm going to [blank]; want to come along/can I get you anything?" Mix it up, too - a movie, a bike ride or walk, an errand.

My own bad-news experience, at least, was that sometimes I needed to circulate, and sometimes I needed to go fetal and screen calls, and the people I appreciated most are the ones who offered concrete things and didn't take no personally. I had two friends who called frequently who had never called much before and who rarely call since. I will never forget them - they just got it, that "normal" rules weren't in force.

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