Ready to Make Amends? Here’s How to Do It Gracefully

Written by: the Editors of goop


Updated: November 1, 2022

Ready to Make Amends? Here’s How to Do It Gracefully
Jenny Taitz

You flip your phone open and your finger hovers over their number. You want to reach out and see how this person is doing, but maybe some time has passed and you don’t know if it feels appropriate. Or maybe the last time you spoke, it didn’t end so well. Maybe it’s an ex and you genuinely want to wish them well. Or perhaps it’s a former colleague and you left a toxic workplace behind. But maybe, you think, some things are better left unsaid.

Not so, says psychologist Jenny Taitz. When a relationship becomes strained or ends, we naturally want to seek out answers or an explanation, but it’s easy to get caught up in endless rumination—the type of spiral that ultimately leads to inaction, says Taitz. She teaches patients strategic ways to think through difficult conversations and how to approach them with care using tools from dialectical behavior therapy, which she shares here. “No matter how hard the conversation is, it can go so much better than you think if you approach it with the right tone and content,” Taitz says. If you’re thinking about reconnecting with someone from your past or you’re avoiding an overdue conversation, Taitz’s process is rooted in self-compassion and self-respect. As she explains: “A lot of times, it just feels good to say what you need.”

A Q&A with Jenny Taitz, PsyD

What’s the first thing to consider if you’re thinking about reaching out to someone from your past?

First, it’s important to keep in mind that every relationship will have its conflicts; it’s inevitable with any long-term bond. Ideally, being able to address a rift in a productive way can make you—and your relationships—stronger.

That’s why, as a general rule, I encourage people to live an approach lifestyle: a life where you face what matters to you rather than avoiding it. But there’s a caveat that applies when it comes to reengaging with a difficult person from your past, whether they’re an estranged family member or an ex: Do it only if you believe that it will ultimately prove healing.

The best way to figure that out is to reflect on your long-term goals and the facts at hand. Are you looking to have this person be a source of emotional support? Are you just hoping to get some emotions off your chest? Is it realistic to think that will happen? Think about whether doing any of the above will make you feel better; if you’re not sure, try making a list of the pros and cons of reaching out versus not.

One thing that’s important to do, whatever the circumstances, is to take your own emotional temperature. If you’re feeling especially lonely or struggling with intense negative emotions, as many of us are right now during the pandemic, know that you’re more at risk of acting impulsively than you might otherwise be. I’ve never had a client who has regretted waiting to send an angry email or holding off on initiating a conversation with a long-lost lover via text at 1 a.m.

Is there ever a time when the past should stay in the past?

That depends. If you’ve repeatedly tried to talk to someone and they’ve continued to dismiss you, you have two choices:

1. You can reconsider the way you’re approaching the person to see if you are able to get a more satisfying result. If you’ve tried reaching out before, it doesn’t mean it’s not worth trying again, especially if you change your strategy.

2. You can decide that it’s time to radically accept the breach, that it has more to do with them than with you and your worth, and that it’s healthy to maintain some emotional distance. It might also help to ask yourself what you want your life to be like and whom you want in it. If you know for sure the person is incapable of offering you what you need, then it may make sense to walk away for self-compassion’s sake.

How would you approach this conversation?

If you decide that it’s wise to speak up, set yourself up for a better conversation by thoughtfully rehearsing an empowering way to give voice to your needs. I like a technique known as DEAR MAN, which comes from dialectical behavior therapy, an approach that teaches practical skills in managing emotions and being effective in relationships. The strategy can help you focus on presenting the facts and your hopes alongside a mutual benefit—all of which can be helpful when you’re aiming to get your needs met.

How it works: DEAR stands for describe the facts, express how you feel, ask for what you want, and reward or reflect on what’s in it for the other person. The MAN part is more about how to deliver your message: (be) mindful, act confident, and negotiate as needed. In other words, focus on your intention, remind yourself of your own worthiness, but strive to be flexible.

DEAR MAN helps us escape some of the usual detours that get in the way of accomplishing our goals. When you start off with too much anger, even if it’s justified, the other person will naturally become defensive. Instead, describe the facts in a straightforward way, then express your feelings. So rather than saying, “You’re selfish” or “You were manipulative,” just describe exactly what happened. For example, “When I told you about my depression and you didn’t follow up, I felt hurt.” By letting yourself be a little vulnerable, you’re giving the other person an opportunity to empathize. Then you can ask for what you’d like to happen—“I’d really appreciate if when I’m struggling, you don’t run but reach out”—since no one can read your mind, as frustrating as that may feel. Given that all relationships are two-way streets, also reflect on what you can offer. You might say, “I promise I won’t go on and on. I care about you and your feelings and want to hear about them and be there for you.”

While making your request, also consider your intensity, by rating it from one (for being silent) to ten (for screaming). Then slow down and adjust your tone, if needed. This isn’t so much about catering to another person as about your feeling emotionally regulated and setting yourself up to be truly heard.



  • Describe the facts

  • Express how you feel

  • Assert or ask for what you want

  • Reinforce or reward


  • Mindful

  • Act confident

  • Negotiate, if needed

How do you check in with yourself in that moment?

To keep your composure, try something called coping ahead. If you feel anxious about something, rather than worrying about it, imagine the situation realistically, knowing what you’re likely to face, then visualize yourself succeeding. Doing these mental rehearsals beforehand triggers the same brain areas that are activated when you’re actually in the situation and increases your competence and chances of success in the moment.

Of course, sometimes things take an unexpected or upsetting turn—one we can’t predict. In that case, take a moment to recalibrate, feel your feet on the floor, take a deep breath, and remind yourself of your ultimate objective. If you’re feeling too intensely, it’s okay to ask to take a break until you feel more clearheaded.

What if you don’t get what you’re hoping for out of the conversation? How do you deal with your own guilt or shame?

A lot of people put too much value on the idea of closure, assuming that a perfect ending with someone will erase pain or suddenly help everything make sense. But it may make more sense to work on radical acceptance—actively accepting the outcome, moment to moment—rather than fighting reality by overanalyzing. Ultimately, you have to be open to what is, even if it’s painful.

How do you take care of yourself after the conversation?

Sometimes you have to let yourself off the hook rather than stewing indefinitely. The term “elephant in the room” is a misnomer—too often the elephant is on your shoulders if you’re carrying resentment or overthinking something that occurred in the past. It helps to have a game plan for self-soothing after anything you anticipate will feel painful. Try scheduling some pleasurable, distracting activities, whether it’s joining an Instagram Live workout class or listening to a crime podcast or doing something relaxing like engaging in a gentle skin-care ritual. Call a friend who you know will nourish and nurture you (though skip a long play-by-play if that’s only going to make you reexperience your pain). Whatever the outcome, beating yourself up and wishing all were different will not be helpful in the long run.

Jennifer Taitz is an assistant clinical professor of psychiatry at UCLA and the author of How to be Single and Happy: Science-Based Strategies for Keeping Your Sanity While Looking for a Soul Mate and End Emotional Eating. She offers her clients at LA CBT DBT, her private practice in Beverly Hills, practical tools to live better.

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