From Sugar Baby to Girlfriend of an Inmate: Part 3

By Katya

Dec 19, 2017

In the previous two installments of this series, I discussed my journey of falling in love with a man who was facing jail time, while simultaneously participating in the sugar bowl. My conflicting feelings about leaving the sugar bowl for a serious relationship have been a recurring theme throughout my story. I’d stopped sugaring once for a boyfriend who proved not to be worth it – was I ready to do it for Dave?

The benefits of an arrangement and those of a relationship sometimes fall on opposite ends of a spectrum. A big question that I asked myself while trying to decide which lifestyle was right for me was “which one will I get more out of?” The answer is anything but simple, since human needs and desires fall into myriad categories and are not fixed, static things, but are ever-changing. I’ll reflect on this difficult choice by describing how I came to my decision and comparing things I loved about each type of dating.

Do I Have the Time/Energy/Resources for a Serious Relationship?

At times, despite wishing I could have a relationship, I lacked the ability to be a stable, consistent factor in someone’s life. Sometimes it was my job or education that got in the way; others, it was family or financial issues. Sugaring made the most sense when I wanted to experience romance on some level, but couldn’t fully commit due to other obligations.

How Deeply Involved Do I Want to Be?

In the aftermath of my break-up with my abusive ex, it would’ve been lunacy for me to jump straight into another relationship. Sure, I’d already fallen in love with Dave, but I wasn’t emotionally ready to live up to the expectations a man typically has of his girlfriend. I couldn’t be someone’s rock when I was healing and learning how to better care for and respect myself. The timing was perfect for establishing a light, no-pressure connection with a sugar daddy.

I Want to Feel Something

As fulfilling as arrangements can be, I eventually found myself wanting a deeper emotional connection than mine allowed. Since arrangements demand varying levels of commitment depending on the terms set in place by the parties involved, it’s possible for some sugar babies to take things to the next level with their daddies. However, I relied on sugaring when I wanted a clearly delineated boundary prohibiting heavy emotional involvement. To keep myself “in check”, I sought sugar daddies with circumstances that limited how deep our attachment could realistically become. Therefore, when I felt ready for a more serious situation, my existing arrangements weren’t options, and it made the most sense to look for a boyfriend instead of a new sugar daddy. Luckily, I already had Dave.

As Milestones are Achieved, Relationship Goals Change

Graduating college was an accomplishment that influenced other changes in my life, including my decision to leave NYC, an increased focus on my career goals, and deciding I was ready to have a boyfriend. At the same time, I wasn’t in a rush to “settle down”. Dave was in jail when I graduated, and we’d been talking daily for several months. We weren’t ready to focus solely on our relationship, but things were going in an established direction. As my life went through many changes at once, the pieces began falling into place accordingly.

Age Had Something To Do with It

Am I too old to sugar? Heck no, not even close! If I hadn’t met Dave, I’d probably still be doing it. But I’m no longer equipped with the mentality that I have infinite time to get my life where I want it to be. A life partner is near the top of my wish list. At almost thirty, it feels like the right time to pay attention to this desire. In terms of priorities, that translates to seizing the opportunity if I think I’ve found “the one”. When I fell for men during my younger years, I was more apt to think ‘I’m having fun dating casually – another one will come along.’

The Heart Wants What it Wants

This is what my choice to leave sugaring ultimately boiled down to: Dave is “the one” – my soulmate. As I stated before, if Dave wasn’t part of my life, I’d most likely continue sugaring until commitment material came along. In fact, when Dave and I agreed to be exclusive, I truthfully wasn’t quite ready to leave the sugar bowl – but love requires sacrifices. Fair is fair – I don’t want him seeing other women, so I’m not going to see other men.

The Best Choice Wasn’t the Easy One

I never felt “trapped” into sugaring, but as Dave and I grew closer, I’d grown to rely on my allowances for supplementary income. In a short-term sense, sugaring was incredibly fulfilling – it bridged a gap between my income and my bills, and provided me with much-needed company and entertainment. Being spoiled made me feel special, and being doted on made me feel beautiful.

I realized, however, that things like new perfume, fancy dinners, travel, and an authentic-but-limited connection didn’t satisfy me the way simple things from Dave did – a letter, a hand-drawn birthday card, the sound of his voice. In fact, I started scheduling dates with my sugar daddy at times that wouldn’t interfere with Dave’s phone calls.

Shortly thereafter, I told my sugar daddy the truth about Dave. To my surprise, he was non-judgmental, mentioning that I’d seemed happier in recent months and encouraging me to follow my heart. We parted ways amicably.

I then made one of the most ballsy (and perhaps crazy) decisions of my life. Having become fed up with the cost and pace of living in NYC, I posted a “housing wanted” ad in the Wisconsin section of Craigslist. However, I soon realized that I’d underestimated the costs of moving.

I then received an e-mail entitled “Opportunity”. A family of six needed a last-minute caretaker for their elderly dog. They were scheduled to depart for a six-week trip to Europe in five days. In exchange for the care of their dog, they offered free room and board.

I responded to the offer with an unhesitating “YES!”

And thus began a fresh, new chapter of my life, as I sit at my laptop in this family’s home, patiently awaiting Dave’s release, at which time we will stay with his sister while we look for our own place.