When To Move On: How Many Chances Should You Give Someone?

Relationships can be beautiful and life-affirming, but they can also be complicated, especially when hurt or disappointment enters the picture. Many people ask, “How many chances should you give someone?” It’s not always easy to know when forgiveness is helping a relationship grow or when it’s preventing you from moving forward.

Small transgressions, such as dismissive comments, forgotten commitments, or inconsistent communication, may seem minor on their own but can accumulate over time. These recurring issues slowly chip away at trust and emotional safety, leaving you asking, “Should I give him another chance?” over and over again.

On the other hand, major breaches of trust or significant life-altering decisions made without your input can deeply shake the foundation of a relationship. One single action may make you question whether or not it’s worth it to stay.

Recognizing the cumulative impact of both large and small hurts is essential when determining whether to give a partner another chance. These events may occur at the very beginning of a relationship, as tiny red flags put you on high alert, leaving you wondering if it’s worth sticking it out. Or, they may come along much later, when your relationship is already serious, and give you a gut-wrenching feeling.

Here, we’ll explore the signs, emotions, and faith-based wisdom that can help you navigate the decision of whether or not to move on from a relationship with clarity and confidence.

How Many Chances Should You Give Someone? A Real-Life Story.

Take the case of a friend of mine who is starting the divorce proceedings with her husband of 15 years. He has been threatening to leave her for more than five years, but she wasn’t willing to give him the satisfaction of giving up on the marriage first.

She felt that if he was serious about divorce, then he would eventually leave; this summer, he finally did.

I used to ask her why she put up with it. He treated her terribly, chipped away at her until she wouldn’t have any patience left for their three children, and then chide her for losing patience with the young kids. Why was she still there? Part of the reason is that she gave him too many chances. She was unable to figure out when to move on, and move up from her marriage.

In the five years of dating prior to getting married, he would break up with her over and over again. She thought she was being the easy-going, reliable, loyal girlfriend by being there for him as he went through law school and family issues. She wanted him to see her as wife material.

Alas, his dissatisfaction with her, and life in general, didn’t stop once they got married. And so for the past five or so years as he would threaten to leave her but didn’t, she kept up the hope that one day he would see her for the loyal wife and dedicated mother that she is. She wasn’t willing to take the blame for their marriage ending because she wasn’t the one giving up on it – he was.

It wasn’t just her who was having trouble figuring out when to move on. By threatening to leave, then staying anyway, he was giving out the most mixed of mixed messages – suggesting he wasn’t clear in his own head, either.

So, was she surprised when he finally said he truly wanted a divorce and found an apartment? No. But she also didn’t totally buy into it and was expecting him to drop it again and stay put. This time, for the last time, he left for good. She still spoke about taking him back if he changed his mind, and that’s when I asked her, “Do you still love him and want to be with him, or is this your ego talking and not wanting to fail at your marriage?” Meanwhile, her husband was being even more of a jerk than usual, trying to get her to hate him so she would give up and stop holding out hope. His plan worked and she is done with their marriage and has accepted their divorce.

This story begs the question: How many chances should you give someone, and how many chances is too many? Whether you’re wondering whether to call it quits in your marriage or are seeing red flags early on in a relationship and are questioning whether you should stick it out, there are several important things to consider.

Choosing to Stay or Walk Away

It’s natural to hope for change, especially if you’ve invested time and emotion into someone. You might find yourself torn between wanting to believe in their potential and needing to protect your peace. Whether you’ve been let down once or multiple times, deciding if this person deserves another chance can stir up deep internal conflict.

Understanding this dilemma means acknowledging both your hopes and your boundaries. Giving someone a second chance is sometimes the right choice. Other times, it can delay the healing you need.

• Second chances can lead to growth if both people commit to change.
• Repeated chances with no progress may lead to more disappointment.
• Your values and well-being should remain at the center of the decision-making process.

Signs That It’s Time to Move On

Staying in a relationship where your needs go unmet, or your trust is repeatedly broken can leave lasting emotional damage. Some signs make it clear that moving on may be the healthier choice:

• They continue the same harmful behavior, even after promising to change.
• You feel emotionally drained, anxious, or insecure in the relationship.
• Communication turns toxic, and problems go unresolved.
• You compromise your values or self-respect to keep the peace.

These red flags aren’t always obvious at first. However, if you notice them recurring, it’s essential to trust your intuition and prioritize your long-term well-being.

Emotional Costs of Staying Too Long

Staying in a relationship that no longer serves you can take a toll. People often underestimate the emotional cost of trying to fix something that isn’t changing.

• Self-doubt: You begin to question your worth or judgment.
• Chronic stress: Emotional tension affects your mental and physical health.
• Isolation: You may withdraw from loved ones or lose your sense of community.
• Spiritual disconnection: When a relationship distracts you from your values, it can affect your faith and peace of mind.

The Role of Boundaries in Giving Second Chances

Sometimes, it’s okay to give someone a second chance. It can be an act of grace, but it’s important to do so with discernment. A second chance may be appropriate when:

• The person takes responsibility for their actions.
• They show genuine remorse.
• They’re actively working to change.
• They change their pattern of behavior.

When considering giving someone another chance, establishing boundaries is essential. They protect your emotional health, help rebuild trust, and ensure that both partners understand the expectations moving forward. Boundaries communicate self-respect and foster a sense of safety in the relationship.

• Set clear communication rules: Establish how and when you’ll discuss difficult topics.
• Define deal-breakers: Be honest about behaviors that you will not tolerate again.
• Ask for accountability: Expect your partner to acknowledge past mistakes and show real change.
• Create space when needed: Time apart can help reset the emotional tone.

Boundaries differ from ultimatums. While ultimatums are a firm set of expectations, boundaries are commitments to your well-being. They help you give another chance without sacrificing your emotional peace.

Practical Steps to Moving On

Once you reach the conclusion that it’s time to move on, the next steps may feel overwhelming. Healing isn’t instant, but you can approach it intentionally.

• Set clear boundaries: Limit contact or go no-contact if needed.
• Seek support: Talk to friends, a therapist, or a spiritual advisor.
• Reflect and journal: Identify what you’ve learned and how you’ve grown.
• Rediscover yourself: Reconnect with hobbies, goals, and community.

Healing doesn’t mean forgetting the past; it means learning from it. It means choosing yourself in the present.

When to Seek Professional Help

Sometimes, emotional clarity requires the guidance of a professional. Individual therapy or couples counseling can help you sort through complicated feelings and patterns, especially if you’re stuck in a cycle of giving endless chances.

You might consider professional help if:

• You’re unsure whether to stay or go.
• You notice patterns in your relationships.
• Your self-esteem has suffered.
• You struggle to envision a healthy future.

According to the American Psychological Association, therapy can improve not only individual well-being but also relationship quality if both partners are willing.

Incorporating Learned Lessons into Future Relationships

One of the gifts of heartbreak is wisdom. Once you move on, take time to apply what you’ve learned to your future relationships. That way, your past experiences can lead to more fulfilling connections.

• Clarify your non-negotiables.
• Notice early red flags.
• Practice open, honest communication.
• Stay grounded in your faith and values.

Letting go isn’t failure. It’s preparation for the kind of relationship you’re truly meant to build.

What Does the Torah Say?

Jewish tradition values forgiveness but also teaches self-respect and wisdom. The Torah reminds us to pursue peace, but not at the cost of justice or personal dignity. For example, in Ecclesiastes 3:1, we read: “To everything there is a season, and a time to every purpose under the heaven.” This includes knowing when to let go.

In Proverbs 4:23, it says: “Above all else, guard your heart, for everything you do flows from it.” Giving someone another chance should never come at the cost of your emotional or spiritual well-being.

Faith can be a powerful guide in moments of uncertainty. Trust that letting go can be an act of strength, not surrender.

What About Divorce?

Jewish law permits divorce as an unfortunate necessity and has for thousands of years. While traditionally, only men could initiate divorce, today, that is no longer the case. Still, many people of the Jewish faith struggle with the question of whether or not to end a marriage and how it may be seen in the eyes of God.

The Torah acknowledges the complexity of relationships and permits divorce under specific circumstances. Deuteronomy 24:1 states: “When a man takes a wife and marries her, and it happens that she does not find favor in his eyes… then let him write her a bill of divorce.” This passage introduces the concept of the get (Jewish bill of divorce), emphasizing that while marriage is sacred, there are times when parting is necessary.

Jewish tradition sees divorce as a last resort, but not a failure. The Talmud reflects this balance by stating, “Even the altar sheds tears when a couple divorces,” highlighting the sorrow of a broken union while also acknowledging its necessity in cases of irreconcilable differences, harm, or disrespect.

In modern Jewish life, divorce is both a personal and communal decision, and the Torah reminds us that peace — shalom — is the highest value, even when that means choosing peace apart rather than together.

When to Move On: The Bottom Line

If you’re asking yourself, “How many chances should you give someone?” take time to reflect, pray, and listen to both your heart and your values. The answer won’t come from guilt or fear but from clarity, confidence, and faith in the path ahead.

You deserve a relationship founded on respect, love, and spiritual harmony. Trust yourself to choose the next right step.