Are You Dating Ready?

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How to know if you pass the dating readiness test

Has the thought crossed your mind that you might, just might, dip your toes into the dating pond once again? Maybe you are recently single after a prior relationship ended. Or maybe you are in a new community. Or maybe you’ve been single parenting for a long time, but now you are an empty nester.

Whatever your circumstance, and however the idea of dating occurs to you, you will also likely ask yourself if you are ready to make the commitment. Because dating will demand your attention. To do it halfheartedly will likely result in halfhearted results.

Accept these two givens: Dating will demand from you both quality time and mental energy. But it will also require that you are ready in seven other ways.

Seven boxes to check off before dating again

If you can answer these next seven questions with a yes, you can be reasonably confident that dating again will work well for you.


  • Have you dealt with your emotional baggage? The first work we must do before entering into a new relationship is to close the doors on any old ones. That’s why I advise people to completely exit a prior relationship before dating. If you are separated, you really aren’t out of your current relationship. If you are newly divorced, you haven’t had time to process the emotional undercurrent created by the divorce process, let alone what came before it. So, give yourself time between your old relationship and dating. Be certain that you are emotionally whole before moving forward to date again.


  • Are you being proactive about your health and fitness? Are you dedicated to taking care of yourself? Have you figured out what represents a work-life balance for you? Are you committed to good physical health? If you are contemplating intimacy again, have you thought about what necessary medical visits would help you prepare?


  • Do you know your own self-worth? Before you begin thinking about the kind of person you’d like to date (not just physical attributes, but also personal qualities), you need to reflect on what you value. And as importantly, you need to believe in yourself! Knowing who you are and what you offer will provide you the confidence to meet new people.


  • Are you a direct communicator? Be honest with yourself on this one. Are you able to say what you mean, and mean what you say? Or is your default not speaking straightforwardly about your dealbreakers? Learning to communicate with clarity and self- assurance is one of the most important ways you can successfully navigate the dating world.


  • Can you handle rejection? Get ready to learn you won’t appeal to everyone you meet (just as you will not be attracted to every person you date). Accepting that we can’t be all things to all people is a prerequisite for re-entering the dating world. In many respects, dating is a numbers game (especially online), and it can be jarring to realize that with dating also comes rejection. But if you know your own self-worth, you’ll be able to carry on and move forward. We each have preferences; dating is our way of exercising them.


  • Do you invest in hobbies and interests? The more you demonstrate passion in life, the more compelling and interesting you will be to others. Having hobbies that you enjoy will make it easier and more fun to identify people with like interests. And finding that common ground is an effective way to build enjoyable and meaningful connections.


  • Is there one (or more words) to describe you? Knowing what label you’d attach to yourself is a fun conversation starter. Call yourself a Dreammaker, a Do-gooder, or a Fairy Godmother. Or acknowledge you are a poet, an author, a coach, a consultant, a teacher, an entrepreneur, or an artist. Tell others who you are – or want to be — and then be confident and excited about what you offer to the world.

 Dating = Preparation

As Selena Gomez reminds us, dating means we have a responsibility to initiate showing up. If you have checked the seven preparedness boxes, you are ready. So, don’t delay. If you want to date, you are the one to make it happen. Go outside and let people see you!

I can’t wait to hear about your success! Share your stories at


  • Kate Somerset

    Kate Somerset is an author pen name for the book “Mom…You Just Need to Get Laid: The Adventures of Dating After Divorce”. Following a divorce after 24 years of marriage, and thirty years of being deeply rooted in professional and volunteer roles in Texas, Kate took a chance on a new life in New York City. She immediately fell in love with Manhattan and the many opportunities it offers. Kate’s book about 15 true dating experiences in New York City is an honest, humorous, and inspirational look on how to give yourself and romance a second chance. One of the most universal struggles faced by all of us – building effective social connections – is the focus of Kate’s monthly column for The Three Tomatoes. Published by Brooklyn Writer’s Press, the book and Ebook are available on Amazon. An audiobook produced by The Three Tomatoes is on Amazon and Audible. Learn more about Kate at

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