In 1975, Paul Simon opined about the “50 ways to leave your lover.” Simon’s classic song focuses on the “how to” of breaking up (“Just drop off the key, Lee”), not on the why or the when.But the why and the when are the hardest parts, so I want to address them here.To begin, ending a low quality relationship can be associated with considerable improvement in our wellbeing. There is a point at which it makes good sense to get out of a bad relationship. This even holds true for children and divorce: Ending a highly conflicted marriage can be good for children in time (a good thing to remember when you’re wondering if you should “stay together for the kids”).Let’s take a look at what to consider before deciding if it’s time to break up.In a prior column, I introduced the idea of an intolerable problem. An intolerable problem can be about virtually anything, but the key element is that you can’t stand it—your relationship problem is ruining your life. You think about it all day; it keeps you up at night, and, quite often, you fight about it with your partner.QUIZ: What’s Your Relationship Style? In many cases, when we have an intolerable problem, we create distance with our partners. We avoid each other, lose our connection, and, over time, drift apart. This distance itself becomes a problem.Fixing Intolerable ProblemsIf you have an intolerable problem, think about whether the problem is solvable. You might come to the conclusion—plain and simple—that your partner is not a reliable or trustworthy person. He or she is, for example, a serial cheater and will likely cheat again. If the problem is unsolvable—and some problems truly are—it’s time to “cut bait” and break up (more on this below).However, perhaps you reason, for example, that you played a role in your partner’s cheating; the two of you had grown apart emotionally and your partner was really just looking for some sort of emotional connection with someone. Well, this sounds like a more solvable problem, and I think you can proceed with caution.If you determine that your problems are solvable, ask yourself if the problem is one of excess or deficit. By that I mean, is the problem one of “too much” (jealousy, talking, selfishness, drinking, rigidity, secrecy, spending) or “not enough” (appreciation, support, sex, emotional openness, alone time)? Be as specific as possible about what you want your partner to do more or less of.Now it’s time to share your thoughts and feelings.COLUMN: How to Fight RightFirst, describe the problem as you see it. To avoid putting your partner on the defense, state your feelings in a descriptive and specific manner.For example, “I’ve gotten to the point where I just can’t handle your jealousy. I know you love me, but every time I get a text from my guy friends, I feel like your response is way out of proportion. You hound me and hound me about it. It’s not just the texting; whenever I go out with my friends I feel like you’re monitoring me all the time about every little detail. For me, it feels like you don’t trust me. I really need and want this to change. What do you think?”In this conversation, you must ask for feedback. Why does this happen? In addition, you must be entirely open to your role in the problems.For example, suppose you want your husband to be more emotionally open with you. You have to be willing to hear him say something like, “Every time we have an emotional discussion, you get so upset that I feel scared to share my feelings. I need you to calm down when we talk about things so that I might be able to go a little deeper.” That’s on you, so to speak.The best possible result from your conversation is to agree on the specific changes that each of you will make to create a better outcome. At that point, it’s time to let go of past frustrations and wait to see if the changes can take hold.A few weeks down the road, maybe a month later, you want to ask yourself if things are getting better in a real and sustainable way. If not, repeat your discussion and identify the barriers to change.I have tremendous confidence that when two people love each other and one person can spell out exactly what’s wrong, positive change will follow.COLUMN: Do You Wish Your Partner Would Change?When to Pull the PlugOf course, there are times when this does not happen. The problems are too entrenched; they’re too overwhelming; and/or, the person won’t or perhaps can’t behave any differently. As far as I see it, you’ve done all you can and it’s probably time to consider ending the relationship.Before you do, ask yourself a series of questions. If the answer is “Yes” to every question, then it’s reasonable to think seriously about ending your relationship.

  • Are you experiencing a relationship problem that’s always on your mind and disrupting the overall quality of your life?
  • Have you repeatedly tried to solve the problem (including, if possible, seeking couple therapy and/or speaking directly with partner about the problem)?
  • Has you partner failed to respond in a way that makes the problem more tolerable?
  • Do you fantasize about what it would be like to live without your partner and to be free of the relationship difficulties?

As I suggested at the outset of this column, ending a bad relationship can lead you to feel much better. If you answered yes to all of these questions, maybe now is the time to consider launching yourself on a new path in life. You can do it!MORE: Beauty Your Way Through a Breakup