How to Get Past the “Nice-Guy” Syndrome

Let’s start with a short story about a fictional guy, yet someone who is very common in our lives.

Troy is the quintessential nice guy. He’s easy-going, always willing to help, and a non-pushy kind of guy. His approach to women is to be the opposite of the supposed “bad boy.” There is one woman he is particularly interested in, Connie, his co-worker.

He becomes friendly, helping complete her projects, staying late so she won’t be by herself, even going to the supply closet to get her extra pens. When Connie was feeling upset because she was in a fight with her best friend, Troy was there to listen, even checking in over the weekend.

Troy feels pretty good about this. “She’s really seeing what a good guy I am,” he tells himself. Connie enjoys it too, particularly the help and friendship.

One Friday, Troy said to Connie, “Boy, what a long week of work, let’s grab a drink and unwind.” A night out sounded good to Connie, so she agreed.

After some appetizers and a couple of drinks, Troy begins his “move.” He tells Connie how much he enjoys her company and that they should really get together, and he invites her over to his place.

Connie feels confused and politely declines. “I enjoy your company Troy as a friend and a coworker, but I’m not interested in more.”

Troy’s face starts to burn; he feels a flush of heat over his body and the anger and confusion and annoyance is at a tipping point. “Are you serious? After all I’ve done for you? Why did you lead me on? I can’t believe you are being like this! What the hell?” He quickly grabs his jacket and walks out of the restaurant, leaving Connie with the bill.

Connie is left there feeling sheepish, confused, and disoriented; she pays the bill, goes home and collects herself.

Do I have to be a jerk to get what I want in relationships?

Often, we think in opposing terms—it’s all or nothing. Either you’re a nice guy or you’re a jerk. But neither of them are very satisfying. They both destroy relationships.

The nice guy is dishonest just like jerks will be dishonest. In our example, Troy was covertly manipulating the situation to “trick” Connie into being with him. If I take care of her, she will take care of my needs without me having to ask for anything. Troy’s lack of confidence and fear of rejection led to him being disingenuous.

In his mind, if he were nice, then Connie would owe him by giving him what he felt he needed and deserved – her relationship.

But he never said this. Instead, he assumed.

If the answer isn’t being a nice guy or being a jerk, what is it?

It’s being assertive. This means clear, direct, honest, and calm communication. It’s being civil and transparent in relationships.

So, what does this mean for our friend Troy? From the start, he needed to be honest with himself about his behaviors. If he expected “something” in return for his help to Connie, his choices would have been:

·       To ask Connie out (“Hey, would you like to grab dinner some time?”)

·       To be honest with Connie from the get-go (“I am interested in you and want to get to know you.”)

·       Or to do nothing (Get himself in a better frame of mind where he doesn’t feel entitled to something just because he acts nice.)

Troy needs to develop healthy boundaries and embrace his desires to go after what he wants without dishonesty. Being assertive includes genuine kindness and compassion. On the other hand, the nice guy pretends to be kind and compassionate to avoid conflict and get acceptance from others.

Evolving beyond the nice guy syndrome

In our story, Troy loses everything, his relationship with Connie, and his “nice-guy” status. Connie is left feeling confused and distrusting of what men’s motives may really be.

For men, it is critical to move beyond the nice guy routine to have a fulfilling life and meaningful relationships. Moving into an assertive way of being allows us to be honest with ourselves and those around us. We feel in control of our lives and don’t feel resentful over something that we actually caused.

Until we take personal responsibility for our lives, we will inevitable feel like a victim of circumstance. If you find yourself relating to Troy, consider exploring what kind of life you want. Often the guidance of a professional is valuable in dropping the nice guy syndrome.

Evolving beyond the nice guy syndrome by ourselves can sometimes be like trying to look at the back of your head with no mirror. We all have blind spots. Fortunately, there are professionals out there that can be a mirror for you and help you to build the life you want.

Are you looking for someone to talk to about relationship challenges? Our counselors are here to help. Reach out Charlotte Counseling & Wellness today to get the support you deserve.


John Syc, LCSW is a therapist in Hamden, CT. He does not claim that therapy will make you happy, but it will make you think. Mr. Syc’s philosophy to therapy is about developing honesty with yourself and with others. His practice primary revolves around men’s issues. His clients appreciate his logical, analytical, and ‘get to the core issue’ approach in his work. More information can be found at





John Syc