The Toll of Bad Dating Experiences

Geplaatst op 24-04-2024

Categorie: Lifestyle

“You are the sum total of everything you’ve ever seen, heard, eaten, smelled, been told, forgot – it’s all there. Everything influences each of us, and because of that I try to make sure that my experiences are positive.”

Maya Angelou

As an avid reader, when I finish a book I often judge it on one criterion: Did it change me? I don’t care if the prose is poetry, or the characters are likable, or whether it made me laugh, or cry. I want to be changed. Ideally, my brain will be a little (or a lot) different than before. Sometimes that change is small. Other books have changed the way I choose to live or the way I see the world.

I believe that all of the choices we make change us in ways both big and small. Most of our choices are small and fairly meaningless. Do you want pizza or Thai tonight? Red sweater or navy? We won’t ever need to consider the “what if” of having made another choice.


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Other choices are hugely important and may have an enormous impact on our lives. Our education, our work, where we live, who we marry.

It is natural and human to make bad choices sometimes. No matter how hard we try to be good, or smart, or rational, we’re going to do stuff we regret later. If we’re lucky, the consequences of our actions won’t be devastating to our lives and the lives of others. We won’t drive drunk, or try heroin, or have a one-night stand with a serial killer. We’ll avoid total self-destruction.

But we will make countless small mistakes, and those do become part of who we are. Making the same mistakes again and again – even if relatively minor – can affect our self-esteem and the way we are perceived by others. We feel that people are responding to us differently or even poorly, but we’re at a loss to figure out why.

Courtney is a young woman I know well. She has had several bad dating experiences recently and she can’t figure out why. She asks, “Tell me what I’m doing wrong! What did I do to deserve this?” She’s made some small mistakes, but they’re adding up and beginning to show.

After graduating college in 2011 Courtney went to work for a consulting firm in DC. She quickly met Josh and dated him seriously for three years. He was her first boyfriend and sexual partner. When she decided that he was not the man she would marry, she ended the relationship and returned to San Francisco, which is home.  She quickly found a dream job and an apartment with a college friend.

In the eight months she’s been back, Courtney has dated three men for 2-3 months each. She had sex with each of them. She ended one relationship, and the other two men disappeared shortly after sex. She isn’t quite sure how she could add three sexual partners and still not be in any relationship! How did this happen?

What did Courtney do right?

In each relationship:

Where did she go wrong?

Courtney wanted things to happen organically. She didn’t want to initiate the awkward DTR in a moment where everything was proceeding in a natural and lovely way.

  1. Eric

Eric was attractive and fun, but he became needy and possessive once they’d had sex. He not only wanted Courtney to be his girlfriend, he wanted her to be his soulmate 24/7 and make decisions for him. Courtney felt overwhelmed. After she ended it, she heard from someone who’d known him in college that he had had two very serious girlfriends before and that his MO was to go all in ASAP.

  1. Ian

Ian was great fun to be around. He focused on Courtney and gave her a lot of attention. He was eager to have sex, but when Courtney said she wasn’t ready, he said he understood and continued the full-court press for her affection. On their last weekend together, he came over for dinner Friday night and stayed for two very romantic days.

When he didn’t text on Monday, Courtney had a bad feeling. On Tuesday he texted that spending the whole weekend with her had “freaked him out” and that he “needed space.” After that he texted intermittently for late night meetups, and Courtney did not respond.

  1. David

Courtney liked David best of all. At 30, he was serious about his career and openly stated he was dating to meet his future wife. He said from the beginning that he wanted to move things forward but at a very gradual pace. He did not pressure Courtney for sex at all. He understood that was not fair since he was being careful about emotional intimacy. After 16 very fun dates he told Courtney he was ready to become more serious. They had sex. He disappeared.

Courtney had met David on Tinder, and they had a mutual Facebook friend. When Courtney asked her friend what she knew about David, she learned that he had been heartbroken when his ex cheated on him last year.

What now?

This isn’t the end of the world. Courtney is not promiscuous by any means, and has never had casual sex in the strict sense of the word. She felt comfortable and assured that she was building something real with each of these men. And yet, she was mistaken. Now she feels emotionally exhausted and discouraged. And it shows. It’s palpable.

Dating is shopping for your life partner. You will most likely date several people before you meet the person you choose to marry. But when each of those relationships destroys a piece of your soul, it takes a toll on your outlook and your emotional well-being. Other people may read that as a weakness. You will attract men who are drawn to that.

Courtney failed to fully evaluate and understand her own feelings before sex, as well as those of her partner. After Eric clung to her possessively, she appreciated Ian’s independent spirit all the more. She failed to notice that he saw her as an attractive woman on his arm rather than someone he might become intimately connected to.

David made it clear he was auditioning Courtney for the role of wife, and he indicated she was passing all his tests with flying colors. She was so pleased it was going well that she failed to notice a guarded quality that would have been obvious if she had paid attention. She may have been acing his tests, but they would continue forever.

We’re all prone to misunderstandings, especially early in a relationship. What would have lessened or even eliminated the disappointment and rejection Courtney eventually felt?

You have to talk about the relationship. You have to talk about sex. When to have it and what it means. You have to say out loud what you believe to be true, what you are willing to give, and under what conditions. Then you have to make sure the other person is on the same exact page.

It’s not romantic. If the relationship works out, you’ll have years to be romantic. Courtney went on about 50 romantic dates with these men, and all she has to show for it is a feeling of having been wrung out.

You can have casual no-strings sex, or you can have relationship sex. Those are the only two options. Casual is the default expectation, so if you want to avoid it, you must get a commitment first.

It won’t prevent every disaster. Eric would have gladly committed to a relationship right away, and perhaps Courtney had no way of knowing how clingy he would become. Ian might have agreed to a relationship at the start of his sexy weekend, and still “freaked out” on Tuesday.

But at least you’ll know that when these things happen, it’s not on you. You were honest, you did your due diligence, it didn’t work out. It wasn’t your mistake.