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15 Questions to Ask Yourself Before You Start Dating Again


By Audrey Cade

So, you’re newly single and have a license to get back out there? If you’ve been in a relationship for a while, the prospect of dating can be downright terrifying!


What if you end up in another bad situation?


What if no one likes you?


What if you don’t find anyone you’re interested in being with?


How the heck do you even get started?


First of all, let me shout it from the rooftops that “you don’t have to date! You don’t even need to be in a relationship to be happy!”


That’s right. You shouldn’t look outside of yourself to find happiness or contentment with your life! This does not mean that being in a quality relationship can’t be a source of happiness or enjoyment; but, the path to personal satisfaction and love starts within yourself!


Be careful not to dust your memories in so much glitter and fancy that you forget the bad parts too.


If you’re fresh from a break-up or a divorce, you may have sentimental longings for the elements of companionship you had in your partnership. Every break-up situation is different, but I’m going to go out on a limb here and speculate that there were also some negative aspects of your relationship- at least enough to send you in separate directions. My point here: be careful not to dust your memories in so much glitter and fancy that you forget the bad parts too!


Don’t linger on all things negative, but take a giant dose of reality and see things for what they were.


Look back

Now, step back, and as objectively as you possibly can, review what went down in your relationship. Make some mental notes about:

  • The dynamics of your relationship (how you communicated, the sense of equity between you, and so on)

  • What aspects of your relationship you felt were lacking (e.g. intimacy, communication, common interests, and values)

  • What brought you together in the first place (did you have a solid foundation of compatibility or was this more of a merging of two lonely people?)

  • How you agreed and disagreed (was their respect, give-and-take, fairness in settling differences, any violence or inappropriate displays of manipulation?)

  • What led to the demise of your relationship? What was your role and what was your partner’s?



Okay, now process all of this valuable information so that you have a sort of “exit report” to summarize what went down in your relationship, how well the two of you fit together, what you would or would not repeat in a future relationship, and what qualities you are now better aware that you would desire in a partner. Now, add this data into your perspective, moving forward, so that you are equipped to even consider dating or relationships!


  • This is when you ask yourself “why do I think I might want to date or enter a relationship?”

  • What do you hope to gain from a relationship (companionship, sex, true love…)?

  • What do you feel you are able to give to a relationship at this time? Are you interested in something serious and long term, or perhaps something more casual for friendship and good times?

  • Are you ready to take the next step because you are truly excited by the opportunity to bust out of the divorce doldrums, or is it because you feel this is what is expected of you now?

  • Are you completely over your former love? Will you find yourself tempted to use your former love as the measuring stick by which you review all prospective newcomers, or have you left that in the past? Is there any part of you jumping into the dating circuit out of a sense of fear of being alone and not having someone?

how-to-know-ready-date-again (1)

Date Yourself

Now ponder how many of your reasons for considering dating could be fulfilled in other ways.


I’m not suggesting a life of solitude and celibacy, but I do highly recommend to any female who will listen that you should be complete as a person and able to stand on your own two feet before ever adding another person to your life! Don’t count on another person to love you, support you, entertain you, or complete you as a human being. We never know what the future brings or how long we have with the ones we love; therefore, it’s unwise to put all of your needs in someone else’s basket when you don’t know if (for whatever reason) they may be capable of fulfilling our hopes!


  • Honestly, do you not feel complete unless you’re in a relationship? If so, what are you afraid of?

  • Do you love yourself? Do you respect yourself? Do you like yourself?

  • Do you believe in yourself?

  • What steps have you taken to protect your interests? Can you support yourself? Do you have a good handle on how to take care of most things in your life?

  • What would you need to do to get your situation in a place that you would be more confident about?


Most likely you will discover that you can afford to take your time, be selective, and add a partner to your life because you want to, and not because you need to.


My suggestion, at this point, is to go ahead and date if you’re ready for it; but, perhaps date yourself first! Fall in love with yourself, rediscover all of your amazing gifts and qualities, dream some dreams, and get to know yourself again. Most likely you will discover that you can afford to take your time, be selective, and add a partner to your life because you want to, and not because you need to.


When the time is right, someone is going to be very fortunate to have you as a date, and you will be in the best mindset to select someone worthy of you!

About the Author
Audrey Cade is the author of “Divorce Matters: help for hurting hearts and why divorce is sometimes the best decision” (on Amazon) and the matriarch of a blended family of eight. She is an experienced “divorce warrior” in the areas of co-parenting, step parenting, parental alienation, and re-marriage, and enjoys sharing these experiences with others who are also committed to raising happy and healthy kids. Audrey’s professional experience is as a case manager social worker with the developmentally disabled, families with young children, and homeless populations. She holds degrees in Early Childhood Education, Human Service & Management, and a Master’s in Psychology. She enjoys family outings, a variety of arts and crafts, cooking, gardening, and writing. She is a featured blogger for Divorced Moms, has work regularly appearing on Divorce Force, and articles appearing in Step Mom Magazine, The Good Men Project, and others.

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