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15 Questions to Help You Decide You're Ready to Date Again

Are you feeling good enough about yourself to go back "on the block?”

Olena Yakobchuk/Shutterstock
Source: Olena Yakobchuk/Shutterstock

Many relationship-seekers feel like the walking wounded. And although they have more ways than ever to meet potential partners, most of those relationships don’t work out. They're still willing to try dating again, but these warriors are understandably wary. They may feel the weight of pre-defeat, with its accompanying self-protection, and struggle hard to keep their cynicism at bay. There can only be so many lost dreams before people lose their positive attitudes, even though they know that pessimism is neither intriguing nor sexy.

Every relationship seeker has a unique set of reasons for why they are still single, which sets the scene for how much dating energy is left to risk. No one can tell another person when to try again, when to retreat, what to change, or how to approach the next opportunity. There are just too many variables to create a stereotype.

What if, for instance, you are an attractive package who’s just been ghosted by someone you thought was in it for the long haul? You’d certainly feel confusion, conflict, devastation, grief, insecurity, hurt, or anger. You might even feel like stalking that partner to try to find enough information to keep yourself from going crazy about such an unbelievable situation. Or perhaps you’d rush too quickly into another relationship just to find temporary solace. You might even be so off balance that you resort to self-destructive escape behaviors.

Or what if you truly believed that you were someone's chosen one, only to find out that one of your partner's prior flames has re-emerged and you’re now back in a competitive race that doesn’t look good for you? You put a lot of energy and thought into selecting that person, you’re weary of looking further, and ready to settle down. Now you feel powerless to stop what is going on and horrified by the fact that you have to start over. You are understandably reluctant to take another chance, yet you have grown used to the joy of a committed relationship. Do you go back to being single and forego another commitment, or do you plunge back into the romantic abyss? Maybe you’re so disillusioned that you can’t think about taking another chance while your heart is still occupied by the one you lost.

Or maybe you weren’t ready to commit just yet, but your partner was. You didn’t want to prematurely promise something you might not be able to deliver, but didn’t want to lose the chance that it could eventually work out. As your partner persevered, did you abandon him or her, fearful of premature entrapment, and now you regret the loss of a relationship that might have eventually mattered?

Many people repeatedly pick the same kind of partners—even though none of those relationships have worked. Or they haven’t really looked at what they are offering, and whether what they want is even available. Perhaps they continue to create fantasy scenarios that aren’t likely to succeed. Then, daunted by too many disappointing losses, they settle too quickly for someone who can’t meet their standards over time. Loneliness can mask logical and effective reasoning.

Balancing all the data is not easy. Ask yourself these important questions:

  • What are your available potential options?
  • Have you recovered from your past losses?
  • Are you willing to realistically look at your marketability?
  • Are you truly open to the possibilities you have?
  • Are you feeling good enough about yourself to go back "on the block?”

You need to be at your best and ready not to repeat past errors before you open yourself to a committed search, and be resilient if the next relationship doesn’t compensate for what you’ve lost.

No one is ready to successfully date again unless they have sufficiently healed from their prior heartbreak. Lost relationships must be grieved appropriately but should never doom the hope for a new love. Those who are still in the throes of sorrow need to wait until they can be honestly optimistic again so they can approach the next relationship ready to give it their best.

If you still feel pessimistic, cynical, insecure, defeated, anxious, angry, martyred, or exploited, you’ll be likely to approach the next relationship warily, at best. Even more worrisome is that you will want that next relationship to make up for all the pain you experienced from the last abandonment. Hyper-vigilant, you might find yourself ready to catch any hint that abandonment may be on the horizon, and seeking constant reassurance from a new partner who isn’t responsible for what happened to you.

The following test could help you know if you are ready to take on a new relationship. Answer the questions as honestly as you can.

Relationship Readiness Questionnaire

Answer the following questions using this scale:

  • 1 = Rarely
  • 2 = Some of the time
  • 3 = Pretty often
  • 4 = A lot of the time
  • 5 = Most of the time
  1. I think about the next person I’m going to fall in love with. ____
  2. I think that I will eventually find the person I want. ____
  3. I believe that I was a worthwhile partner. ____
  4. I trust that the future holds some great new relationship adventures. ____
  5. People get over the pain from their lost relationships. ____
  6. I believe that losing that important relationship has made me a stronger person. ____
  7. My friends tell me that I’m healed from my loss. ____
  8. I think of the good things I did in the relationship. ____
  9. I believe that my partner did truly care for me. ____
  10. I still trust that people are basically good. ­­­____
  11. I treasure the positives in intimate relationships. ____
  12. I believe that I’ve learned what I need to know to try dating again. ____
  13. I feel renewed confidence in knowing what to do differently the next time around. ____
  14. I trust that most people “ghost” other people because they don’t want to hurt them. ____
  15. Things work out the way they’re supposed to. ____

Now add up your total score:

  • 1-15: You're not ready to date yet.
  • 16-30: You should probably wait a bit and focus on hanging out with good people who love you.
  • 31-45: You’re beginning to heal.
  • 46-60: You're very close.
  • 61-75: It's time to get back out there.

Don’t be discouraged if your score indicates that you’re not ready to go back out there. Dating is hard for everyone, especially when there are so many unknowns. Even when things go well most of the time, it is not easy to date again after you’ve been disillusioned by an unexpected or premature ending. Confidence comes from success, but it can also come from building resilience through continuous honing of your approach.

The more you value yourself, understand what you want and can give, and see relationships as the potentially hazardous but mystical adventures they can be, the more effectively you will be able to discern the good from the bad. It is difficult to keep your self-esteem up in the face of consecutive disappointments, but you can eventually find the partner you want if your search stays light-hearted and smart. Looking for a partner is no different from looking for anything else in life that you want to last. Stay in a sacred place, maintain your aliveness, and stay open to transformation.

Most people are universally attracted to people who are in love with life and who bounce back from loss with renewed commitment and excitement. It is more difficult for anyone to date as their losses mount, but you can still give it your all each time you try again. That kind of courage and optimism will always be contagious and highly valued on the dating market.

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