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.