Every Wednesday is Tip Day.
This Wednesday: Eight tips for finding the right thing to say in a difficult situation.

I often feel like I don’t know the right thing to say. I’ll be desperate to find the right words, but in a tough situation, I just don’t know what to say to make a person feel better. I often find myself switching the topic of the conversation — so quickly that I’ve changed it before I realize what I’ve done.

I’ve been trying to come up with some tips to help me figure out what to say. This is what I’ve figured out so far:

1. Try to identify the real problem. It’s quite common for people (like me) to be upset about something, but then to pretend that they’re really upset about something else. Often, when a person’s reaction seems disproporationate to the purported cause, you can figure out what the real problem is, if you try. Once, the Big Girl came crying to me and said, “Everyone pays more attention to the Little Girl than to me!” I had a rare moment of wisdom enough to bite back my first responses: “You know that’s not true,” or “Didn’t I just play ten game of Blink with you?” Instead, I said, “No matter what, you know that you are our most precious, darling girl, and no one would ever forget about you, or think that someone else is more important than you.” That was what she needed to hear, and she skipped off.

You can’t make someone feel better if you’re not talking about the right topic, so taking the time to identify the real problem is a key step.

2. Don’t assume that you know what’s going to happen next. A friend told me that it really upset him, during his separation, when people spoke about his relationship as if divorce were inevitable. Similarly, even positive predictions like “It’s all going to work out” or “You’ll be as good as new” or “Of course you’re going to get that job/get engaged/get into that program” often aren’t very reassuring.

3. Find the right level of questions to ask. People really differ on what kind of conversations they like to have. Some people like to answer probing questions and to get into the details. Other people are just the opposite. So start with general and vague questions, like “How’s it going?” or “How are you doing?” and feel your way.

4. Don’t react with judgment. When something bad happens to someone, the people around him or her often try to identify a “mistake” so that they can reassure themselves that they’re safe, because they would never have made that mistake. But saying things like, “Well, I always said you should stop smoking,” “I never trusted her,” “You should have diversified your investments,” or “You know, you never set any good limits” is NOT helpful.

5. Resist the temptation to show empathy by drawing a comparison to your own painful experience. This sounds like a good idea, but from what I can tell, it doesn’t work very well. A friend whose baby died told me how enraged he was by people who compared his loss to their loss of beloved pets (yes, this really happened, more than once). And a friend whose child has a life-threatening illness was infuriated when people said they understood how upset she was, because they’d been through a divorce. Trying to show empathy by comparing your pain to another person’s is, apparently, not very comforting.

6. Acknowledge the reality of other people’s feelings. This tip comes from all-time favorite parenting book, How to Talk So Kids Will Listen & Listen So Kids Will Talk, and it’s just as applicable to adults as to children. Often, people just want someone to acknowledge how they feel. It can be tempting to say things like, “You’re not really mad,” or “There’s no reason to be so upset,” or “You were never happy in that job in the first place.” But denying people’s feelings adds to their frustration; acknowledging bad feelings helps the feelings to dissipate. This strategy is harder than it sounds to follow, but it really works.

7. Follow their lead. When I’ve talked to people who are very upset about something, I’ve noticed that they often keep circling back to the same point. It seems to help them to keep talking about that same one issue. It’s not always obvious why some aspect of a problem would be the most worrisome, and I used to try to move the conversation along, but now I think that it’s most helpful to follow a person’s lead and to keep talking about whatever is weighing most heavily.

8. Think about what a person needs to hear. Sometimes it’s not obvious that something needs to be said; you must be alert to people’s unspoken thoughts. A friend of mine was very close to her in-laws. She told me that when her brother-in-law got engaged, she felt jealous of his fiancée and was worried about feeling displaced in a relationship that was important to her. There wasn’t any reason for her to worry, but that was how she felt. One night at dinner, the entire family spent the whole time talking about the wedding, and afterward, her mother-in-law said to her privately, in a very loving voice, “Jill, you know you’ll always have a special place in our heart.” Jill told me that she almost started crying, it meant so much to her.

I thought this was just about the perfect thing to say. Her mother-in-law guessed what Jill might be feeling, and wanted to reassure her. She didn’t deny what my friend was feeling. She wasn’t dismissive of the new daughter-in-law. She didn’t make a comparison. But she said exactly what my friend needed to hear.

I wish I had many more tips. When you’ve been in a tough situation, what kinds of conversations have made you feel better (or worse)? Or what rules do you follow to find the right words to say?

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Interested in starting your own Happiness Project? If you’d like to take a look at my Resolutions Chart, for inspiration, just email me at grubin, then the “at” sign, then gretchenrubin dot com. No need to write anything more than “Resolutions Chart” in the subject line.