Back in my younger days, I maintained a stable of lovers I held on retainer. When I wasn’t in a serious relationship, I could call on one to keep me company for a limited time. Each short-term arrangement was carefully planned, never lasting longer than 4–5 months. After that, emotions could develop, so a break was necessary. While not perfect, the system usually worked, keeping both parties satisfied. At the start of this year, I ended all contracts and became a free agent.

Last week, I got an unexpected IM from a guy I know well. “SG, I’m really attracted to you. I’m not good at dating right now. The recession has me stressed, but I’d enjoy a no-strings-attached romp with you.” Really? This isn’t how you negotiate a lover. Timing, strategy, and understanding are essential before entering any arrangement. Casual or not, a careful plan ensures both parties know boundaries, expectations, and the reality of what’s being offered.

There are several essential steps before drafting a lover contract. First, spend time with your prospect in public and solo; this reveals their true personality outside the bedroom. Second, you have to like them as a person and friend—who wants to share intimacy with someone they dislike? Third, learn their preferences in bed gradually, avoiding rushing or ruining potential chemistry. And finally, discuss an exit plan—what happens if things go wrong, and who will handle it gracefully?

Needless to say, I’ll turn down this offer. The market is shaky, and I’d rather wait for someone who meets my standards. Timing matters, even in casual encounters. Waiting ensures a “sure thing” instead of risking disappointment or drama. Being selective doesn’t make you cold; it guarantees quality, respect, and mutual enjoyment. A lover contract, while playful, works best when boundaries, personality, and preferences are fully understood and mutually agreed upon.