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Without a doubt, being an escort has its potential risks and possibility to get harmed. Today’s post is all about the emotional risks of escorting, namely: what happens if fondness (or even love) starts to develop between a sex worker and her client. Is it even possible to build a relationship between two people who initially started dating on a paid basis? Do they ever stand a chance? 

Like any other job, sex work can be exciting, dynamic, and stimulating—and deeply frustrating, disheartening, and painfully boring. The main distinguishing factor is that it’s often based on intimately personal interactions. Work closely with enough people, and there’s a high probability of hitting it off, on some level with a few clients.

These intimate bonds are one of the joys of sex work, but they can also be tricky. Sex workers often enforce strict boundaries for their own safety, and while finding a personal connection with a trusted client can feel refreshing, this can still be professionally and emotionally risky. Getting too close can blur the line between paid companion and personal friendship, and (in rare cases) a transactional relationship can start to feel like something more. But work is work, and navigating this ambiguous emotional territory with a client can become too complicated, or too painful to continue. When things get too personal, it may be time to say goodbye—which can come with complex feelings.

My non-representative research contains real stories of sex workers operating in diverse areas of the business. During their professional years, they all experienced  real feelings and sad break-ups with their favourite clients. 

The first story is about Jessica, who was streaming a live cam show when she first met “Jamie”. After throwing her some generous tips in her public chat, he requested a private cam-to-cam show. The slightly upward angle of his webcam wasn’t the most flattering, but, even hunched over his computer and stroking his penis, he was undeniably hot.

Jamie sent Jessica a message immediately after the session concluded to thank her for her services, then bought a custom video and several nude photos. He asked to see her again soon for a longer video session. Jessica was thrilled: she’d not only locked down an exceptionally sweet, respectful new regular who tipped well, but one she felt instant chemistry with. They sexted nonstop for the next few days—and also talked about their favourite movies and podcasts, even sharing their experiences as survivors of sexual assault. Interacting with her regulars was part of the job, and it always felt like a job, but talking to Jamie was different. Jessica was completely infatuated.

According to Jamie’s Twitter profile, he lived in another state, and she knew he had a young kid and a serious girlfriend, so the chances of ever meeting her new crush in person were slim. Still, she was happy to pursue a flirty friendship with someone whom, under different circumstances, she could be much more than a paid sexual object. After a few weeks, the conversations with Jamie became sporadic. He’d occasionally resurface to tell her how much he missed her, pop into her chatroom to remind her that she was his favourite girl, or ask for a phone call just to hear her voice. After a few weeks when Jessica sent him several unanswered messages, she stopped pursuing him. Their “breakup” was more of a slow, painful fade-out, which left her hurt and embarrassed that she’d let herself develop a crush on a guy from her chatroom. I do believe that she had real feelings for him, and possible he genuinely liked her too, but a crush like this will end sooner or later. She might miss their conversations, but surely she misses his money more. 

Hannah, a sex worker in Long Beach, California who recently ended an eight-year relationship with her sugar daddy, said some sex workers she knows refuse to offer “girlfriend experience” or similar services that might offer clients the opportunity to get too close. “Sex work can be a lot of intimacy, and you spend so much time with these men,” Hannah said. She believes anyone who performs this kind of intimate work could potentially develop genuine feelings for their client, regardless of their experience level. I completely agree with this statement. At the end of the day, sex workers are human beings with real feelings and ability to love, hate and get carried away by someone special. 

Beyond mutual camaraderie, genuinely romantic feelings can blur professional lines for both sex workers and their clients. Twenty-nine-year-old cam model and professional dominatrix Julia Ryan was 19 and fairly new to sex work when a madame friend introduced her to an attractive, successful, and generous client. “He lived in Texas, so he would come out to see me in Tennessee four to five times a month,” Ryan said. “He always took me to the most amazing restaurants and bought me gifts.” Ryan fell hard. “The sex was out of this world—I was gaga over him. He made me feel so special, and even talked about marriage.”

Ryan believed he loved her, but she couldn’t shake the suspicion that he was too good to be true. During one of their last dates, the client stopped to make a quick run into a store, leaving Ryan alone in his car. She dug into the glove compartment, where she found insurance paperwork with another woman’s name on it. “I Googled her later and found all her social media and her business stuff,” said Ryan. “He led me to think he was single and just worked a lot, and hid the fact that he had a full-blown family.” Ryan was furious and hurt. “I confronted him and slapped him across the face. I was so mad, I ripped up the envelope of money he gave me that final night.” The client didn’t argue with her or try to defend his behaviour, and after he walked away, they never spoke again. “I blocked him on everything—total ghost mode,” said Ryan. Despite how hurt she felt, she still remembers their relationship somewhat fondly: “He was the first guy to ever make me squirt across the room,” she said. That’s definitely a bonus!

Lastly, losing a favourite client can be more bittersweet than explosive. Nicole’s story is one like that. She was both happy and heartbroken when one client decided it was time to move on. “When we first met, he was shy and reserved. It made me weak in the knees,” she said. “I related to that shyness.” Over time, Nicole’s client started feeling more comfortable around her, and their conversations became personal. “I really began to enjoy being by his side. I remember us cheering each other on in our goals,” Nicole said. “He was an amazing cook. He often gave me extra homemade jams and jellies he made, while telling me about these free online university courses he listened to while preparing them.”

After a few years, Nicole was surprised when her client said they needed to have a serious, strictly platonic talk. “My palms immediately got sweaty,” she said. The client said he could no longer see Nicole, because, thanks to her, he had met someone. He explained that during their encounters over the years, he had gained the confidence to date and ask for what he wanted in a relationship. He had met a partner to share that journey with. Nicole was delighted to see him take that leap of faith. Today Nicole and her client no longer keep in touch, but she cherishes the time they spent together. “I still think of him and smile, and I wish him the best,” Nicole said. “A heartbreak can sometimes be unexpectedly sweet.”

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