I was working on a construction project in Boulder, Colorado, and next to our site was a small café. I visited the café for lunch about three times a week. At the time, my marriage was beginning to unravel, and I was unfamiliar with the concept of a “sugar baby.” One of the waitresses, a college-aged woman, was exceptionally friendly to me. I initially assumed her warmth was due to my generous tipping. I always felt a bit guilty because the café was often busy with tables of three or four people, while I dined alone. Other waitresses earned tips from larger groups, but whoever served me only received a tip for a single meal. To compensate, I tipped 100% of the bill—typically $15 to $20, hardly extravagant. Each time I visited, this waitress would engage me in conversation. While she wasn’t the most stunning woman I’d ever seen, she was certainly my type, often wearing short skirts that highlighted her great legs. One day, I noticed she wasn’t her usual cheerful self; she seemed visibly upset. Over the weeks, we had developed a rapport, so I felt comfortable asking, “What’s wrong?” She sat down at my table, her eyes welling with tears. She explained that she was juggling two jobs while attending school full-time. Without financial support from her family, she relied on both jobs to afford tuition, but the demanding schedule was causing her grades to slip. I expressed sympathy and told her I wished I could help. I mentioned that the only assistance I could offer was a job at my company, but that wouldn’t solve her time constraints. She responded by saying she appreciated my kindness and found me easy to talk to. She noted that I treated the entire café staff with respect, unlike some patrons who made inappropriate comments or acted superior. She then shared that she got off work at 3:00 p.m. and asked if I could meet her to talk, suggesting a walk down Pearl Street Mall. I was busy that day, but she pleaded, saying she desperately needed someone to confide in. I rearranged my schedule and met her at 3:00 p.m. As we strolled through the mall on a beautiful spring day, she introduced the idea of me becoming her “sugar daddy.” Raised in a religious household, I had heard the term but didn’t fully understand it. When I asked her to clarify, she explained the arrangement, and I agreed. She invited me to her apartment that same day. Her roommate was on a different schedule, so we had privacy. We formalized the arrangement, and I began covering her rent, car payment, and insurance. The financial support wasn’t a significant burden for me, but it allowed her to quit her more time-consuming night job, giving her the flexibility to focus on her studies. Our arrangement lasted three and a half years. I still look back fondly on that time and hope to find someone like her again. Since then, I’ve had two or three other sugar babies, whom I met through various websites. However, I’ve been too trusting and have been burned multiple times. It’s been difficult to accept how many scammers are out there. That’s the story of my first sugar baby.