Working with Criminals and Inmates Took a Toll on My Love Life, Says Former Prison Worker

Kendra Capalbo, a former clinical social worker who spent 15 years working in a maximum-security prison, has revealed how her job completely devastated her love life.

In her role, the 46-year-old performed mental health assessments for inmates, including murderers, rapists, and criminals. Dealing with these dangerous individuals on a daily basis had a disastrous impact on Kendra’s romantic relationships.

Constantly interacting with these inmates made it difficult for Kendra to let her guard down and trust the men she dated, resulting in her reluctance to pursue committed relationships.

“When you spend most of your time in an environment like a prison, you start to develop a jaded view of the world,” explained Kendra, who is now a licensed sex and couples therapist, in an interview with

“While I genuinely believe that a significant number of incarcerated individuals are good people who made mistakes or were wrongfully convicted, there are also many who are not.

“Listening to countless stories of their crimes, being constantly lied to, and being aware of inmates trying to manipulate me or the system, as well as hearing their derogatory views of women, all contributed to me becoming extremely mistrustful and guarded. I would describe myself as rough around the edges now.

“I’m not sure if I chose to work in a prison because of my disposition, or if my disposition developed as a result of working in a prison.

“Unfortunately, this style didn’t work for everyone in the dating pool. It was challenging for me to let my guard down outside of work.”

At the beginning of her career at the Rhode Island Adult Correctional Facility, Kendra went years without going on a single date, influenced by the impact of her job.

“A lot of the inmates were extremely charming,” she recalled. “I could understand how women could be drawn to them, but I also overheard many conversations among them, where they were not aware of my presence.

“Hearing the details of their crimes, particularly those involving women and children, and witnessing the justifications they used for their behavior made it even more difficult for me to trust.

“For example, I never allowed a dinner date to pay for my meal because I wanted to ensure that I didn’t owe them anything. This energy I emitted was toxic and likely pushed potential partners away.”

However, after developing a crush while on vacation, Kendra decided to reenter the dating world. Unfortunately, her foray into dating did not yield positive results.

“I joke about developing a crush on a guy my friend and I met during a cruise,” she shared. “Nothing came of it, but it reminded me of those butterfly-type feelings and motivated me to give dating another try.

“However, once I made that decision, the lack of success I experienced significantly impacted my self-esteem. At the time, I didn’t recognize the connection between my job and my self-esteem, so I internalized it as personal rejection.

“It wasn’t until I left that career and allowed my true self to emerge that I realized how much of a wall I had built around me. Slowly, I began dismantling that wall.”

Eventually, the toll became too much for Kendra, and she decided to explore other career avenues, particularly in therapy. While still working at the prison, she began doing private practice work and discovered a passion for couples therapy.

“I never even considered leaving the prison as a viable option; it felt like a life sentence,” Kendra explained. “However, as I started to delve into private practice work with clients who genuinely wanted to engage in therapy, I noticed a stark difference in how I felt. Unlike at the prison, where the system dictated who I met with, and most of them did not want to see me, doing couples therapy not only energized me but also made me realize my preference for working with couples rather than individuals.

“One day, I looked at the numbers and had a lightbulb moment. I realized I wasn’t actually trapped and that I could leave the prison from a financial perspective.”

Fortunately, Kendra’s love life also took a positive turn. In 2016, at the age of 40, she met her now-husband, James, 50, through an online dating site, and they tied the knot in July 2020.

“I think my experience working with couples made me realize how much I genuinely wanted to be in a relationship,” Kendra shared. “Even though couples often have their issues, I could see the love and their determination to fight for their marriages, and I desired that for myself.

“My guard was still up, but Jim could see through it and was patient as it slowly came down. Jim was incredibly transparent, almost to a fault, from our first date. His genuine nature made me feel like I wasn’t being manipulated, which was one of my concerns due to my work in the prison.”

Despite the challenges she faced, Kendra does not regret her time working in the prison. She is now thriving in her new career and is content with her life.

“I’m doing great now,” she affirmed. “I have always believed that every step in life leads you to where you are meant to be, and I feel like I’ve reached that place. Looking back, I can see the path so clearly, and while there are things I might have wished went differently, I am happy with where it all led me.

“The lessons I’ve learned, mostly from the most challenging moments in my life, have been invaluable. I strive to use them to improve my career and all the relationships in my life, most importantly, the one with my husband.”

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