The Most Important Question to Ask Yourself Before Dating Again

This piece is written by Jennifer Hurtvitz. Jennifer is a Relationship Expert, Dating Coach, best- selling author, and host of the award-winning Doing Relationships Right Podcast. Divorced since 2014, Jennifer lives in Charlotte with her two awesome, college-aged sons (18 and 20).

Many clients ask, “When is the best time to start dating after my divorce?” or “How long should I wait to get back on the apps after a break-up?” Contrary to what some experts believe, I don’t think there is a set amount of time, nor do I feel you have to be the “perfect version” of yourself to begin dating! You only have to be comfortable with being alone, feel confident and have an optimistic dating mindset. You will never be perfect! And that’s okay. I’m constantly growing and evolving, looking to be a better version of myself- I hope I’m never “perfect.” There will always be room for improvement.

Don’t wait, be happy with who you are, and get out there! Dating takes practice; baby steps, keep your expectations low, and have fun.

But wait… forget the WHEN — what about your WHY?

Sometimes, coaches get so caught up in the timing of the process that we forget how essential the reasoning behind the action can be. Ask yourself this: Why do you want to date? Not are you ready, or when is the best time?


  • Maybe it’s to find a long-term relationship?
  • Maybe to find a friend or companion to travel or hang out with?
  • Maybe, it’s to meet new people and get out of the house?

Any above are perfectly acceptable “whys” if YOU are comfortable, honest, and open from the beginning. Being transparent about your “end game” will make dating easier for you and alleviate stress and anxiety. Knowing why you want to date is far more important than whether you are ready. Hold off if your “why” is to fill a void from losing your spouse or making yourself feel more confident. Value and respect yourself enough so when you start dating, you’re not coming from a place of fear of rejection. Remember, this is about how YOU feel about your date, not how they feel about you. If you lack confidence and have low self-worth, take more time.

Can your “why” change? Sure! As you grow and evolve, maybe what you want from a partner will also; no issue with that! Just remember your motivation for dating should remain the same regardless of the person you have chosen to date. If you want an LTR, then own it! Please don’t say you don’t, to be agreeable, or swipe right on a person that doesn’t want what you want. Can’t fit a square peg in a round hole, ladies!

Know you’re why, be patient with yourself and give yourself some grace. There is nothing easy about dating after divorce — especially as a working mom. But you can do it!

Happy dating and healthy relationships!

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