Dating After Divorce: What If I Choose Wrong Again?

When we decide to step back into the dating world, we come face-to-face with our greatest fear of all…

What if we choose wrong again?

This fear kept me single for more than 15 years and had me swear off marriage just to make sure I was never trapped with the wrong person again!

Dating After Divorce: What If I Choose Wrong Again?

Fear was running my relationship show!

To make matters worse, I could not find any good advice on how I should make the right choice.  

The common advice I would receive was some version of: “You will just know,” or “You will figure it out…”

This felt a lot like: "Just cross your fingers and hope the next one will just work out somehow!"

Have you ever felt this way on your dating journey?

The thought of having to cross my fingers and just hope my next relationship would just work out made me crazy!  

So I studied, dated, read, dated…and grew.

I now know that there are three primary mistakes that most of us make when dating after divorce. (I sure did! I did them all!) Which causes our journey to toe tingling love to be a bumpy one.

Avoid these mistakes and your worries of choosing wrong again will begin to ease up.

Here Are The Three Primary Mistakes To Avoid When Dating After Divorce:

1. Bonding Over BaggageBaggage…we all have it. It’s perfectly natural to try to look for similarities when you’re meeting someone new, but please take my advice. Bonding over your baggage is NOT the way to do it! Yes, it can feel therapeutic. It often feels like you’re connecting on a deeper level and the ability to connect feels great. However, bonding over negative experiences does not create the best foundation for a healthy relationship. I am not suggesting that you run from or hide from your past, however, when we bond because of our baggage, our past can quickly become our future as well. To avoid this pitfall…admit what your past has been AND make sure it is not the only place you are bonding with a potential partner. Focus on where you and your date can connect and bond outside of the baggage of the past…beginning with today.


2. Confusing Desires vs. Deal Breakers - “I will make a list, and I will stick to this list no matter what and this will ensure that I am successful in creating the relationship that I truly desire.”

While a list is a good thing for creating clarity for you…it will not help you overcome the fear we are ultimately facing (choosing wrong again).

As a matter of fact: Your list can heighten your fears and frustrations and give you an excuse to RUN!

You are going to need to move past your list to overcome the panic and fear of choosing wrong.  

My clients often confuse desires and deal-breakers and it’s such a shame. Because of this, it is helpful for us to understand the meaning of each.


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Desire: to wish or long for; crave; want

Deal-breaker: any issue or factor that is significant enough to terminate a negotiation
(or in this case, a potential relationship)

AND, while we are breaking things down, let’s take a look at negotiation because it is part of the meaning of deal breakers for some insights as well.

Negotiation: discussion aimed at reaching an agreement

When we are dating, we have a discussion to reach agreement on whether to move forward or NOT based on our deal breakers.

Deal-breakers are our personal beliefs and values that need to be present in our relationship. They are our guide to help us know when to move forward in a relationship, or NOT move forward when they are present. 

Desires are what we “want” and wish for. They are nice to have, but not a deal-breaker.

It’s great to have a list of “needs” and “wants” when seeking out a potential partner. 

It’s even better if the items on your list reflect experiences and lessons you’ve learned via past relationships. 

Let me give you a few examples:

  • It might be that you would want your next date to be 6 feet tall but if he isn’t, is it really a deal breaker for you?  
  • Or perhaps you would want her to enjoy 80s rock bands but is it a NEED? 
  • Having standards is wonderful but a long list of WANTS closes you off to many potentially wonderful people. The more open you are, the more possibilities you have.

Now it is your turn. What are your deal breakers? 

Here is a wonderful tool to help you map out your deal breakers before you begin dating: 

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3. Expecting Sparks to Fly…Immediately - We’ve become conditioned to think that feeling an immediate spark, or chemistry, is essential to determining whether or not to give a date a chance.  

Sure, an instant attraction can and often does occur but what if it doesn’t? Does it mean you shouldn’t consider a second date? No! 

Many factors can contribute to lack of perceived chemistry on a first date.  

Feeling awkward, shy, or nervous when meeting for the first time, a less than ideal setting for the date, perhaps one or both of you isn’t having the best day…

Whatever the reason, the energy of the date can be greatly altered and account for the lack of spark.  

If you find yourself unsure of how to move forward after a date, ask yourself the following question: 

Do I have even the slightest bit of interest or excitement about seeing this person again?

If the answer is “yes,” it’s worth going out with them again. It can take a few tries sometimes in order for you both to feel safe and secure enough to fully open up. If you are still not feeling anything after the second or third date…well, that’s an entirely different story and should be addressed.  

You don’t want to get too far into a relationship if there isn’t any spark there. Don’t worry about choosing wrong anymore it just sucks the joy out of your dating journey.

Don’t worry about choosing wrong anymore it just sucks the joy out of your dating journey.



Take it one date, one conversation, one choice at a time while you follow the spark to love.

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