Dear Sarah,
"Is it better to be honest even when the truth might make the person you're talking to uncomfortable?"
Honesty and lying are not the only choices.
In my view, you are under no obligation to tell people anything that you do not wish to tell them. Consideration for their likely awkward feelings is a good motive – a good reason not to tell them the whole truth and possibly none of the truth. That is not the same as lying.
If you know your hairdresser as a close friend, sharing some details about your life seems natural, but I suspect most hairdressers just chat to make the session seem like a natural encounter between friends, even when it isn't.
Maybe they and their customers are just uncomfortable with silence (or "dead air," in the case of discussing Melissa) so they chat about the news or they gossip.
I used to go to a barber, now deceased, whose shallow commentary on current events (based on things he'd heard from other customers and on radio) discouraged me from participating, so I'd say things like "I've heard about that" or "People have a lot of strong opinions on that, don't they?" or "I don't know much about that."
Usually when someone says, "How are you?" he or she is just making a friendly social grunt that acknowledges you. In most cases, it's not a question designed to elicit a full or honest answer about negative aspects of your life.
If I'm not really happy at that moment, I sometimes say the flippant "Still walking" or ""Not bad" or "OK, I guess" or sometimes, more fully, "It's been a bit of a rough day, but pretty good overall." Usually, they'd don't ask what's been rough about my day; they may even be getting the hint that I don't wish to go into detail.
In the case of Melissa, you could go into a bit of honest detail with the hairdresser if you wished.
"Sadly, Melissa died in a crash (or plane crash) recently."
"Oh, that's awful. What happened?"
"I'd prefer not to go into detail here [that is, "with you, right now, in a public place"]. I'm sure you understand." The hairdresser may or may not understand, but you'd have just set your conversational limits.
With the hairdresser, rather than saying "My sister lives in Kalispell" you could have said, "I've been there a few times" or "I've heard it's a pretty nice town" or "Do you go back often?"
As for your work colleague in D.C., I think it might have been better to share a bit of intimacy. "Well, Snibbles is my parents' cat, but I suppose you realize he/she doesn't really know how to answer friend requests. He/she used to be my sister's cat and she set up the FB page. My sister died a few years ago and no one knows the password."
It's 4:22 in the morning; I woke up after less than three hours of sleep, so should go back to bed.
More to come,
Greg
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