This is Part 2 in a series of writings about my journey from Sugar Baby to girlfriend of an inmate. In the aftermath of an abusive relationship and while in a sugar arrangement, I fell in love with Dave*, a man I’d met online two years before, and who lived halfway across the country. We’d never met in person, and although I’d been hesitant to pursue a relationship with Dave, my feelings for him were too strong to ignore. Eventually, I caved and allowed myself to entertain the possibility of a future together.
Aside from distance, there was a major hurdle preventing us from taking things to the next step: I hadn’t been honest with Dave about my sugaring, out of a fear of being unfairly judged. Unbeknownst to me, Dave was also keeping a secret.
The Floodgate Opens
At the time, I was a senior at a prestigious university in Manhattan. As a 27-year-old divorcee who’d gotten a late start on college, I was relieved to almost be done earning my Bachelor’s. I was also feeling burned out by single life and casual dating. The sugar bowl was a lot of fun and was conducive to my lifestyle at the time, so the idea of leaving it for a serious relationship was anxiety-inducing. However, my feelings for Dave and the persisting desire for a deep, committed relationship became increasingly difficult to ignore.
One night after class, I was unwinding at a bar in Manhattan’s Greenwich Village while awaiting the arrival of my sugar daddy. Dave and I were texting at about the same time I received some disappointing news: my sugar daddy canceled last-minute due to an emergency – and it wasn’t the first time.
My mood suddenly turned sour, and Dave detected it immediately. When he asked me what was wrong, I impulsively dumped the entire truth on him about my sugaring. To my surprise, his response was simply “I’m not judging you. In fact, I wish I could take care of you. But I can’t, because I’m facing criminal charges, and I’ve been drained in lawyer fees.”
Dave proceeded to explain that he’d pled guilty to a first-time, non-violent offense, and that his sentencing date was approaching. He anticipated a maximum of two months in county lock-up.
Where Do We Go From Here
Learning one another’s secrets was a game changer: Dave and I were brought closer than ever, and now felt comfortable being completely candid with one another. However, we were left with the burning question of how to proceed with our relationship, if at all. Instead of confronting the issue head-on, we continued along the trajectory of falling further in love via our constant chats. Neither of us wanted to think about his approaching sentencing date.
One January evening, Dave’s sister texted me as I rode home on the subway after a date with my sugar daddy. Her message informed me that despite the two months they’d anticipated, Dave was sentenced to a year in county jail. My heart sank as I fought tears. It wasn’t until this precise moment that I realized how much I’d come to rely on Dave as a source of emotional support, and how I’d grown to naturally expect a future with him.
Life Goes On…Sort Of
For the first three months of Dave’s incarceration, there was no correspondence between us. I had his mailing address, but every time I sat down and started a letter, I hesitated to put my true feelings into words, assuming I would be an added burden to everything he was already going through. Countless pieces of crumpled-up paper made their way into my wastebasket.
I continued sugaring and even looked for a boyfriend. While I hadn’t given up on Dave, I had my doubts: a relationship that was complicated by distance now faced the additional obstacle of incarceration. However, I found myself unable to remain distracted from the thought of Dave by dates with sugar daddies and men from singles apps.
One day while grabbing my mail, I noticed a county jail return address on an envelope. I ran into my apartment and ripped it open. It was a letter from Dave, detailing the depth of his feelings for me and stating that he hoped we could have a future together. I wrote back and included some photos of myself that he’d asked for.
Upon receipt of my letter, Dave called me. Hearing his voice made my heart race. Based on how elated I was, I knew that our connection wasn’t worth passing up simply because of the complications that came along with it.
A Blossoming Love
From thereon out, Dave and I talked on the phone daily and regularly sent letters back-and-forth. I stopped sugaring when we both expressed wanting exclusivity. I knew I’d miss the sugar bowl, but leaving was the right decision.
We’ve established a solid foundation of love upon which to build our relationship. When Dave gets released in December, the hardest part is yet to come: he’ll need to find work as a convicted felon and re-adjust to life “on the outside”.
After graduating from NYU, I came to Wisconsin to await Dave’s release and test out life in an area with a cheaper cost-of-living. Moving made sense for both my financial situation and my relationship.
While maintaining a realistic perspective that the relationship isn’t guaranteed to work out, I’d regret not trying. Dave and I both need a fresh start – for me, a geographic change was in order. He intends to stay on a straight path after his release and regain his independence. We’ve never been physically intimate, because jail visits are facilitated through video chat, but our bond has proven strong enough to withstand the forces of physical distance and incarceration. This decision couldn’t feel more right and is worth every risk that comes along with it!