How Do You Know When You are Ready for a New Relationship?

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Sally Connolly, LCSW, LMFT has been a therapist for over 30 years, specializing in work with couples, families and relationships. She has expertise with clients ...Read More

Questions to Ask Yourself After Ending One Relationship and Before Beginning Another

Many people make the mistake of thinking that the best way to heal from a broken heart is to get right back into a new relationship. Rarely is that the best way to heal. It is like trying to cover up a wound without cleaning it out first.


Lost relationships deserve to be grieved. Even if the choice was yours to end it, there is still the loss of the hopes and the dreams that must be faced.

Go slowly into a new relationship. Take time, significant time. While there is no “magic number” for how long to wait before beginning a new relationship, think in terms of months rather than weeks. Some experts suggest that you should wait a month for every year that you were in the relationship before jumping back into another one.

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Thinking, journaling, talking out loud with a trusted friend or therapist will help you walk this walk in a way that will allow you to come out stronger, smarter and with more emotional intelligence.

Here are some suggestions for questions to journal, think and talk out loud about. Be sure to go through them several times. With distance, there can be new understanding.

Questions about the relationship that just ended

Look to the relationship that has just ended for learning about yourself in a relationship. Understand, as well as you can, what you did well and what might help you choose and/or be a better partner in a new relationship.

These questions are good ones to ask yourself as a relationship is ending, several weeks after it is over and again several months later. Distance often brings new perspective.

  • Why do I think that my last relationship ended?
  • What would my partner say was the reason that the relationship did not work?
  • Is there any pattern between the ending of this relationship and the ending of other relationships?
  • Is this relationship truly over or is there unfinished business with that partner?
  • How intense are my feelings for my former partner, both positive and negative?
  • Have I accepted completely the end of the relationship and the hope that it will pick up again some day?
  • Have I fully grieved the loss of that relationship?

Questions about my choice in a partner

Some people seem to make the same mistakes over and over again. Choices are often made that are familiar and feel comfortable. When the choices are healthy ones, then the possibility of a good relationship is high. When choices in partners are negative ones, it is only a matter of time before the relationship develops problems.

Ask yourself these questions about how you make choices in a partner.

  • What have I learned about the choices that I make in partners?
  • Do I seem to be picking the same kind of person or making the same mistakes over and over again when making a choice? (Do I often pick partners that are disrespectful? Distant? Have difficulty with affection? Abusive? Have addictive personalities?, etc.)
  • Have I clearly identified what characteristics, qualities and values are important to me in a partner?
  • Am I looking to find something in someone else that I don’t have in myself?
  • Am I more concerned about whether or not the other person is right for me than if I am right for them?
  • Do I know that I cannot change another person?

Questions about my part in the relationship, both the positive and the parts needing change

No relationship ends completely because of one person. Even if the choice was a bad one, part of the reason it got bad has to do with the dance between you and your partner. Carefully look at how you handled situations and ways that you treated your partner.

  • What have I learned that I have done well in relationships?
  • What have I learned that I need to do differently?
  • Do I sabotage myself in relationships?
  • Have I received any advice from a trusted source that might give me information about how to be a better partner in a relationship?

Questions about my readiness for a new relationship

Being part of a healthy relationship requires being a whole and healthy person. While it is very nice to have a companion and a witness to your life, it is important to feel comfortable with yourself and with your life when you are on your own and before entering a new relationship. Here are some questions to help you assess your readiness for a new relations.

  • Do I feel strongly about myself and about my own identity?
  • Do I get my sense of self from people that I date?
  • Do I know the components of an emotionally intelligent relationship?
  • Do I know how to be a healthy and emotionally intelligent partner?
  • Do I have other things going on in my life that are fulfilling and rewarding or do I spend my life around my dating partner?
  • Do I have other intimate (non-sexual) relationships?
  • Is there anything that I am afraid of or avoiding?
  • Do I have any behaviors that are out of control (drinking, shopping, work, etc.)?
  • Do I know what I want to get out of dating … a committed relationship? Fun?
  • Do I know how to be open and direct about my needs with my partner?

No one ever figures everything out about themselves and others in relationships; however, the better that you define what you want and need in a relationship, the more likely it is that you will find someone who can be whole, healthy and a good fit for you. The more you understand yourself and ways to observe, act and assess yourself and your partner, the more likely you are to be half of an emotionally intelligent relationship.

How Long Should You Wait to Date After a Breakup

Breakups can be hard. They can leave you feeling lonely and broken, with the question of when is it okay to start dating again lingering in your mind. You may feel ready to jump back into the dating scene right away or you may be hesitant, not sure if you’re ready for a new relationship yet. No matter how you feel, there is no one-size-fits-all approach.

Dating after a breakup depends on many factors, such as the length of the relationship, the reasons for the breakup, and how you’re feeling mentally and emotionally. It is up to you to decide when you feel ready to start dating again. If the breakup was particularly painful or difficult, it may be beneficial to wait longer before beginning a new relationship. Give yourself time to work through any feelings of depression, guilt, or loneliness that you may be experiencing. Talking with friends and family can be a great way to process your emotions, as well as getting professional help if needed.

There are several online therapy providers available if you’re looking for quick and accessible therapists. Some popular online therapy services include BetterHelp, Amwell, Talkspace, and ReGain.

When you do decide to start dating again, take things slow if needed. Start with casual outings and conversations, such as going out for coffee or having lunch together. Take your time getting to know the person before deciding whether or not this is someone you want to pursue a relationship with.

There is no “right” timeline – everyone moves at their own pace and it is important to be gentle with yourself. It is perfectly normal to want companionship and love after a breakup, but take time to make sure you are ready before entering a new relationship.

Keep Reading By Author Sally Connolly, LCSW, LMFT
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