Dating Again After Divorce

Why dating someone that feels familiar can sometimes be a red flag.

Posted Aug 17, 2020

You know that feeling when you go on a date with someone and you think, “I am so comfortable with this person, it is like I have known them forever.” Guess what? You have. When we feel an instant connection or familiarity with someone it is often because their behavior is similar to someone in our past. We might find ourselves saying, “It is so easy with this person.” 

This can at first feel really exciting and reassuring. Being with someone who reminds us of our past might be a positive sign for some, but for many of us having gone through divorce, this can be a red flag.  

I remember vividly when I told a long-time client of mine that in order to find the right partner, she would have to avoid dating anyone she felt a deep pull toward. She was devastated and angry. She had just met the “perfect” man. He was everything she was looking for and most importantly it was easy to be together. 

Once her anger subsided a bit, I asked her to write down the traits that felt familiar to her. She wrote funny, adventurous, confident, brash, and provocative. These were all characteristics that excited her and she found magnetizing. I said, “He sounds like a lot of fun. Does he remind you of anyone you know?” She took a long pause, fell back into the couch, and said, “Yup, my dad.” 

Now, my client’s dad was a fine person, but he had left her feeling alone when she was a child. His arrogance made it difficult for her to connect to him and get the deep love she deserved. As a result, she became a perfectionist, trying to be the best student, athlete, friend, and daughter to guarantee his love.  

Their dynamic was challenging for her and often left her feeling not good enough. Once she made the connection between the behavior of her dad and this new guy she was dating, I asked, “What do you think might end up happening for you if you stayed with this person?” Without hesitation, she said, “I know what would happen because it has happened with most men I am attracted to. We would have a great whirlwind time at first and then he would start to withdraw and I would do whatever I can to get his attention. The more perfect of a girlfriend I try to be, the more resentful I will become. I have been down this road many times.”

This is an example of how we can be drawn to familiar patterns even if they are negative. Sometimes what we know feels better than what we don’t. To be successful in dating post-divorce, I am going to encourage you to spend time with people who have behaviors that are different than what you are used to.

Just the other day, a woman in my online membership program, called Afterglow, shared about her first date in 20 years. She explained that when she spent time with this man, she was surprised by how attentive he was. She hadn’t had the experience in years, and maybe ever, of a man listening to her so intensely. She explained with great insight that a part of her liked it and a part of her was uncomfortable.

Of course, she was! When we experience a new behavior from someone, we naturally question it. My suggestion is to try the opposite action. If you have the desire to never see the person again, then try one more date. We often cut relationships off prematurely when something feels uncomfortable. What would it be like to try to lean into the discomfort rather than avoid it?

Facing fears is the cornerstone of cognitive-behavioral therapy, the empirically validated treatment for anxiety and mood disorders. My suggestion is to consider dating someone different from what feels 100% comfortable as an opportunity to see what else you might learn about them and to challenge the assumption that there is only one person for you.