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Perfect Time #1: After the Wedding (Way, Way After...)

Back when I was younger and idealistic, I believed that if you thought your friend's upcoming wedding was a bad idea, you should gently, lovingly tell her. I did this twice: once, the night before the wedding, when the groom was partying at an "exotic dancer" club and the bride was crying in the corner of the hotel suite, and then again when a (different) bride revealed to me that she had had an affair a few weeks before the wedding was to take place. In both cases, I took a big, horrible breath and posed the question, "Are you sure you want to do this?"

And in both cases, the brides got married anyway. And then things got distressing. They didn't not talk to me for a few years; they simply talked to me in bright, chipper sunshine voices about their jobs and houses and plans for vacation, but never, never about their spouses. I did my part in these conversations. I was as bright, chipper and sunshiny as a dandelion watered with Dr Pepper. I didn't want to lose my friends. I knew this phony veneer was the only way we were going to make it through.

Until...a few years later, when the first one called to tell me her husband had stolen all of her money, and the second one called and told me she was depressed: She was not in love with her husband, she wondered if she'd ever been in love, and she wasn't sure what she was going to do exactly. Right then I realized that it was in this moment that I should have talked about my worries. Because—and I don't care what anybody says—people about to be married do not want to hear it. Deciding to get married is just one of those things you do on your own. Heartache, on the other hand, is something you do with a friend, especially one who has a list of specific details about why that guy is a lout, starting with the time he cheated at Scrabble.

Perfect Time #2: Before the Margarita That You Drank in Order to Tell the Truth

It always seems like a good idea at the time: You slurp down a nice, strong, salt-rimmed drink to buck yourself up, and after that fortifying margarita (or three), you're 97.82 percent more likely to respond truthfully and extravagantly to your long-time pal when she asks what you really think about her decision to move to China. You're likely to bring up the time she got homesick in Florida over spring break. You're likely to bring up the fact that she has no job there and is leaving a well-paying one behind in order to go to Szechuan cooking school. You might mention that she's allergic to rice, and you might even do some lavish imitations of her trying to ride a bicycle.

In other words, you will tell too much truth, with too many repetitions of essentially the same story, in more and more hyperbolic terms. Worse, if she is also tipsy, she will have a similarly exaggerated response: She will cry, and you will sit there in La Mexicana on Route 17 imagining what would have happened if you both had just eaten at the Thai place that only serves tea with condensed milk, where, instead, you would have said, "Hmm...China? I know you've been looking for some kind of radical life change, but you could just go to L.A. It has a lot of Chinese cooking schools, cars you know how to drive—and beaches."

Perfect Time #3: When You've Done the Same Thing, Only with Worse Results, and You Have Proof

This one applies to pants, haircuts, formal gowns and anything else about our external selves that we're not supposed to care about, but we do. If you're going to weigh in on these aspects of your friends' choices, you need to come prepared with evidence from your own experience. (Models and superhumans can stop reading right now because you do not have the sufficient evidence. You might think you do—a patch of cellulite on your thigh, or pants that split up the butt, right on the runway—but that's essentially a microscopic spot of mold on a slice of manna.)

For example, I have a friend who is hitting her mid 40s. She works very hard; she's single; she was feeling very dumpy. She hired a photographer to take some glamorous pictures of her. She was very excited about this, and I was very excited too. Sometimes something completely external can radically transform the internal.

The shoot took place on a Friday, and that night, my friend sent me the pictures. She asked me what I thought because she was going to put them up on her online dating profile; she was going to put them up on her fridge; she was going to send them out to family. And that is right when I had to send her an email that was not such a good idea: These photos did not bring out her best angles. (Left unsaid: "You look dead in these pictures! You are green! And what is with the twitchy thing your lip keeps doing?") I also told her that this happens to lots of people because taking pictures is hard. I know this because my husband is always trying to take pretty pictures of me so I will feel less dumpy, and this is what happened the last time he tried in Oregon.

Once you share a picture of yourself like this, the conversation quickly turns from what was wrong with your friend's photo to "What is wrong with you? Why do you show this to people? And which Adderall-addicted grandma of yours sent you that hat?"

The same technique applies to jeans. I have a certain slinky, saddle-bag-enlarging, thigh-thickening, ankle-fattening pair that I wear over to my friend's house when I must inform her that those pants she bought for $150 (and wore twice, so she can't return them) are not her friend. "We all have pants that are not friends," I say. "Look at me."

When you really think about it, engaging in this kind of self-abasement to make your friend feel better is the real act of honesty. You're being straight-up about yourself.

Perfect Time #4: The Moment You Stumble into the One Fragile, Vulnerable Room in the Burning House

Have you noticed something? Problems, unlike yogurt, don't come in single servings. I'm going to give a painful example. I have a friend who constantly has family crises. Her marriage is a struggle; her kids have learning difficulties; her husband is in and out of work. We will meet for brunch, and the news on her end will go something like this: "I don't know, maybe everybody has problems. People fight, don't they? Do you think Jim and I fight too much? Basically, I think it's about power. He wants it. I want it. I think sometimes it affects the kids, because little Sammy is wetting the bed again."

I used to just let her go. She was right on every count, and I wasn't sure if she would listen if I said something—not that she's a narcissist; she was simply upset and didn't get much time to just talk and be listened to.

That is, until I realized after several of these "chats" that I was really worried about little Sammy. Now I do this:
Her: I don't know, maybe everybody has problems.
Me: [Nod]
Her: People fight, don't they?
Me: [Nod]
Her: Do you think Jim and I fight too much?
Me: [Nod]
Her: Basically, I think it's about power. He wants it. I want it.
Me: [Nod]
Her: I think sometimes it affects the kids.
Me: I think so too. Kids sense upheaval. It's really stressful for them. Have you thought about taking him to talk to somebody?
Waiting to be honest about the one point in the whole dark cavalcade that feels the most crucial to you, instead of trying to tackle every problem (in other words, trying to focus on one room of the burning house, instead of the whole burning house), is more likely to help your friend, even if it's in a smaller way, instead of overwhelming her with commentary and not helping her at all.

Perfect Time #5: If (and Only If) You Can Pull Off a Dan Rather

Sometimes you find things out. They are never the things you want to find out. By chance, you discover that your friend's mother has cancer and she's keeping it a secret from the family. Or you suspect your friend might be losing her job. The usual dilemma is whether or not to tell your friend.

Assuming that you want to be honest, that you want to lead a life without the fuss, agony and guilt of cover-ups, consider sticking to a plan I call The Uninterpreted Facts. This is what newscasters do, and everybody loves them, even when they're sitting up there saying things like "a famine has spread through the Sudan, and all the children are dying."

Let me give a few examples: About your friend's mother, instead of saying "I think your mom has cancer," you might say, "I ran into your mother at the hospital yesterday. We were both in the chemo wing." About your friend's job, instead of saying "you haven't been working very hard, and I think your boss—who's friends with my boss—is going to lay you off," you could say, "There's a memo about layoffs in the break room. Your boss is in the office with the head of Human Resources." In the face of this news delivered in a neutral tone, the friend is either going to wonder why this happened and/or why you brought it up, then reach some conclusions on her own—or she will not because she's not ready to deal with it. Either way, you'll have given her the honest information, and she will have the choice about how to move forward.

Perfect Time #6: When Your Friend Is Not There...

In other words, when you're alone. Being truthful with others starts with being truthful with yourself. This is one of those excruciating realities that we all have to live with—because to be honest, nobody wants to be honest with themselves. I certainly don't. I'd much prefer to think I gave my sweater to my neighbor because I'm a nice lady, not because I don't like the sweater and I want to use my neighbor's garden next week and she likes the sweater.

The real truth is complex and clunky and doesn't come with three free smaller bits of wisdom and a set of apple corers. It's not sexy, and it doesn't make you look younger. But it is one of those things that gets more valuable as you learn to use it on yourself with the same compassion you would use with other people. Telling yourself the truth as your husband walks out ("I pushed too hard," "I didn't listen," "I was never really committed," etc.) isn't at all enlightening—and may possibly ruin your self-esteem. Three days later, after you've calmed down, that same unwelcome but much-needed bit of honesty could change your life.

Leigh Newman is a columnist for Oprah.com. Follow her on Twitter: @leighnew

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