5 Questions to Ask About Anyone in Your Life (including myself)

By Amanda Fortini

"Self-deception remains the most difficult deception," Joan Didion wrote in her 1968 essay "On Self-Respect." Few of us are lucky enough to have avoided the heartbreak that comes from trusting someone who subsequently betrays us. The original transgression, the betrayal, is painful, but even more painful is the realization that we've betrayed ourselves—that we saw the signs and could have predicted the disastrous outcome from the start.

Why are we willing to overlook qualities or behaviors that nag us as problematic? Why don't we listen to our blaring inner alarms? Maybe it's simply that we want to see the best in people. Or, if you're anything like I was during my 20s, when I dated a succession of rude, angry and passive-aggressive guys, your motivations are frequently less noble: loneliness, lust, boredom, insecurity. Often, too, others are on their best behavior in the honeymoon stage of a relationship; we allow ourselves to be seduced by fun times or grand gestures and are then shocked when a very different person emerges in times of adversity.

If we had a set of questions that would allow us to figure when someone has made an honest mistake and when they've shown you, to quote Maya Angelou, "who they are," we might save ourselves a tremendous amount of pain and grief. Not to mention energy. And drama. Instead of vigilantly trying to interpret another person's actions (Was that malicious or a misunderstanding? Did he get busy and forget to call, or was he just plain rude?), we could determine for ourselves what's really going on. We went to a handful of experts for help coming up with five questions to ask about any relationship—whether a friendship, a romance or a business partnership:

How does this person treat the busboy?

"When people are acting disrespectful, contemptuous or superior, pay attention to that," says John Gottman, PhD, author of The Seven Principles for Making Marriage Work and co-founder, with his wife Julie Gottman, PhD, of the Gottman Institute. It can be easy to justify less-than-stellar behavior when it's directed toward yourself but more difficult to ignore it when you see it aimed at others. We can learn a lot by observing how the person in question treats his family, his friends, the waiter at the restaurant who forgets to put the dressing on the side. "If they kick their dog," says Harville Hendrix, PhD, best-selling author of Getting the Love You Want, "they're probably not going to treat you very well either."

Is this person truthful?

This seems an obvious question—and yet we're frequently willing to overlook or explain away a person's tendency to fib, mislead, or omit crucial details. Does your friend say she's staying home and later post pictures from a party online? Does your spouse tell you he's investing money back into the family business when he's really spending it on the sly? "You simply can't have a relationship if you lie to one another," says Robert Sternberg, PhD, provost and senior vice president of Oklahoma State University and author of The New Psychology of Love.

Knowing whether someone is honest is important because it raises another question: Can I trust this person? "If you don't have trust, you have no reliability," Hendrix says. "You can't make predictions, and if you can't make predictions then you have anxiety and conflict."

I had precisely this experience when I first began dating my fiancé. The issue was minor—I was flaky when it came to keeping travel commitments—but the effects on our relationship were not. I'd cancel or move a flight without a thought, my fiancé would get anxious and critical, and an argument would ensue. Eventually, I realized that it all came down to one fundamental issue: He couldn't trust me to follow through with plans. Not only was I showing him who I was with this behavior (disorganized, terrible at managing time, anxious when pinned down by commitments), I was also, I realized after we discussed it, showing him who I didn't want to be.

Does this person listen to me, or does he or she "listen"?

This question is particularly relevant now. Your friend, partner or spouse should not be texting, emailing or tweeting midconversation. A few years ago, when I was living in Los Angeles, I spent a lot of time with a movie producer friend whose fingers were flying across his BlackBerry keys each time we met for a meal. "I'm listening," he'd say, eyes lowered. But I decided that his refusal to put down his phone and converse was a clear signal that he valued his cellular goings-on above our friendship, and I quit making plans with him. "In every conversation, a person needs to stop and make eye contact and focus," says Hendrix. This approach may, in the long run, save you time: "It takes two or three minutes," says Hendrix, "but if you don't listen, you're going to have a fight, and it's two or three hours."

Is this person willing to be vulnerable?

"Vulnerability means a person's feelings are available in the conversation," says Hendrix. It also means having the ability (and the willingness) to fess up to guilt, anxiety or confusion. We've all known the friend who can't admit she made a mistake or that she doesn't have all the answers. "Most people," says Hendrix, "live in what is called a 'defended relationship.' They're afraid to be vulnerable. They're afraid to say, 'I'm scared,' or, 'I feel needy,' or, 'I have horrible memories.'" But the silence of someone who's disinclined to lower his defenses can speak quite loudly, telegraphing a fear of intimacy or a desire to remain emotionally in control.

How does this person fight?

Someone who is unable to communicate or be vulnerable often lacks the ability to resolve conflicts—what Jette Simon, a clinical therapist who runs the Washington D.C. Training Institute for Couples Therapy, calls "the capacity to repair." This trait is crucial, of course, because there's not a strife-free relationship on the planet. "It's not so much having conflicts that's going to determine the quality of your relationship," says Simon, "but can you each take responsibility for what you did and then go back and share?" In other words, does this person have the ability to admit that what he or she said at the dinner party or in the board meeting was hurtful? Or, if you're the contrite party, does your apology reach open, forgiving ears? As Gottman says, "You need to be able to talk about a regrettable incident or a fight you've had, to figure out what went wrong and how to make it better, without getting back into it." People who fight to win are showing you that making a point, proving they're right or asserting their own ego is ultimately more important to them than the relationship.

As helpful as these questions are, the experts agree that when you have a gnawing feeling that someone's behavior isn't right, trust that information, subtle though it may be. Believe the person, yes, but above all, believe yourself.