The Right Time to Start Dating Again

Many singles come to Innovative Match (IM) asking how long it will be before they should start dating after losing a loved one, whether they experienced an unfortunate death or a divorce. While there is no perfect timeline, the questions and insights served up in this IM blog can help you to find and use your own “dating/relationship compass."

Lisa Field’s article on WebMD is an IM favorite. Field’s piece aggregates expert advice from leading authors, PhDs, counselors and psychologists focused on divorce and relationships and provides excellent insights to help you assess your “dating readiness.”

Being ready to get back on The Romance Highway depends on your emotional state and your motivation. Re-entering the dating arena could take a few months or years. However, if you are able to thoroughly address the following questions, you may be on the right path:

1. What have you learned from your past relationships?

Each ended partnership is a lesson. In order to avoid repeating things that caused you pain in the past, you should examine the pros and cons of each major previous relationship. We highlighted a proven exercise in a past blog that you can do with a confidante. If you can be honest about what worked and, more importantly, what didn’t work with your exes, you may be ready to look for a new partner.

2. How are you different today?

When we jump back into the dating scene, we often falsely believe that we are the same person whom we were when we engaged with our last partner. Perform a self-assessment – how have you changed since then? Have you cultivated new hobbies or have your priorities shifted? Maybe the exit of your last partner has lifted a burden off of your shoulders and now you want to pursue ideas you have kept bottled up inside. You are likely a changed person from when you entered your last relationship, whether changes happened because of choice or because of circumstance. Realize those changes and the changes you want to make before engaging with someone new.

3. How are you going to meet new people?

This is perhaps the hardest question to answer, even when you are emotionally ready to start dating again. Some people may choose to invest in matchmaking services. Cassie Zampa-Keim, IM’s CEO and Founder, is a firm believer that (whether you invest in professional search services or not) you should also be your own matchmaker.

Finding a new date is a bit like networking; put behind your fears and attend events and engage in activities that interest you! Ask friends and family to introduce you to other singles. Online dating can seem like an ocean, but if you know what you’re looking for you can create a strong pool of candidates to choose from. Use the sites and search parameters that are best for your current situation. Most importantly, be honest about your status: separated, divorced, widowed, etc. Only when you can acknowledge your current state are you truly ready to move forward.


It may feel uncomfortable to let yourself be vulnerable in the dating arena, especially since it has been a while since you’ve tried to meet other singles. While you may experience “learning detours” and “emotional speed bumps” along the way, with the right attitude and resilience, you can present the best version of yourself to potential matches and enjoy an expansive, new relationship journey. Once you have established what you want and learned from your past relationships, you are likely to be successful on The Romance Highway.