Coaching clients often ask, “How will I know when it’s time to start dating again after a break-up?” This is a classic question and one that is 100% subjective. I’ve heard silly things like waiting one-fourth of the time of the relationship (for example, if you dated 4 years, then wait 1 year before you begin dating again) or “the best way to get over someone is to get under someone new”. I disagree 100%.

But the decision of when to date again depends on several factors. The biggest factor is “self-awareness”. Eckhart Tolle says that, “Awareness is the greatest agent for change”. If you’re interested in NOT repeating patterns of former relationships and laying a new foundation for who and how you date, you must first be aware of your motives and rationale for diving back into dating. 

Here are some things to ask yourself before deciding whether it’s time to move forward or just chill and heal for a bit longer. As usual, be honest with yourself: Why do you want to date again?

  1. Are you trying to get over your ex? Some people prefer to jump back into the dating scene right away, to get over their ex. From my experience (and the experience of my clients), this could lead to temporary, rebound relationships and the hurt feelings and disappointment that come with them. Allow yourself some additional time to heal from the previous situation before diving into something new.
  2. Are you trying to fill a void? If you’re dating because you’re trying to fill a void in your life, consider another alternative. Better yet, take some time to figure out exactly what’s missing in your life BEFORE you recruit someone to fill that void. It could be boredom (get a new hobby). It could be feeling insecure without a man (love yourself first). And it could be that you’re missing sex (there are plenty of toys that can do the trick and take the edge off WITHOUT the risk and drama). Another human being is NOT a temporary placeholder that you can plug and play when you need to fill a void.
  3. Are you whole by yourself? I hate the notion that a relationship “completes us”. Bullshit! You need to be whole and healthy and in love with yourself whether you have a significant other or not. Relationships should supplement all the good stuff we already have going on. If you feel less than whole, work on building yourself up before you begin to date. Figure out what that means for you (it’s different for everyone) but you owe it to yourself to fill your own cup and date from your overflow.
  4. Can you share your story without getting emotional? At some point in the first few dates, you may be asked one of the infamous questions like, “What happened?” or “Why did your last relationship end”? Can you give a high-level overview of the situation without getting misty-eyed? I say “high-level” because the person you’re on the date with does NOT need to know all the messy details when you’re on the first few dates. This is not an invitation to vent. If you can something like, “We cared about each other but we had different values and wanted different things in a relationship” instead of “He was a total asshole, liar and a cheater”.

I once went on a date and spent the entire time ugly crying (literal tears) about my ex. The guy I was on the date with was a sweetheart, trying to comfort me while convincing the waiter that he was not the reason I was crying. Of course, I never heard from him again.

In essence, only YOU can decide when the time is right to begin dating again. Whatever your motives are, be transparent with the other person before things start to move too fast. One date could easily turn to two or three and the next thing you know, you’re in a relationship at best or a “situationship” at worst. Practice self-awareness. Hold yourself accountable. Be wise and guard your heart…..not just from others but from your own justifications.

“Yes, love yourself. But also, analyze and be critical of how you think, act and behave. Self-love without self-awareness is useless. Be accountable.”

– Unknown