When Feelings Show Up: Care, Clarity, and the Agreement We Kept

I knew from the get-go that developing feelings would be a risk for me. My friends warned me about this from the moment I told them I was thinking about becoming a sugar baby. In fact, they teased me relentlessly about my ability to fall in love with “anyone with a pulse and a nice smile.”  Don’t get the wrong impression. Underneath the teasing, my friends were genuinely worried about me getting my heart broken by some unfeeling older man. And the more I tried to justify myself with platitudes like “I promise, having a sugar daddy will be different. I’ll know that it’s no strings attached. I can compartmentalize,” the more they rolled their eyes.

Despite their warnings, I started chatting with potential sugar daddies online. And, as I got to know them virtually, I felt like I was doing a pretty good job. I wasn’t allowing my emotions to get away from me. I was keeping things formal and distant.

The real test came when it was time for my first in-person meeting. I had chosen the guy who, honestly, had impressed me the least, at least in terms of being able to wow me with conversation. He seemed perfectly normal, even a little bit boring, and only mildly good-looking (Steve, if you’re reading this, I’m so sorry for this description. It was just a first impression!) And he seemed really busy with work and his own life, so it seemed like it might be a good match for someone as easily wooed as me.

To my dismay, Steve was so much more compelling in person than online. He was charming and sweet. I found him interesting, and there was never a lull in the conversation. And, here’s the kicker: he had a cute smile. Dang.

On the way home, I texted the group chat, “Well, I think I’m cooked. He’s a cutie.” In response, lots of straight-faced emojis and a few “girl, get out while you still can” and “we’ll have the ice cream waiting for you when it goes south.”

But, I still hadn’t actually formalized anything with Steve yet, so I decided to talk to him about what my friends called “the flaw in my programming,” i.e., my romantic side. I told him that maybe this wasn’t going to be a good fit after all because I was already starting to feel butterflies when I saw a text from him.

“Look,” he wrote back. “I was married for a long time and haven’t really dated since the divorce a few years ago. What I mean is that it’s not like you’re talking to some ladies' man, here, who doesn’t care about your feelings. And, I agree that we need to have some boundaries because even though I’m not a total jerk, I also am not looking for my second wife (I hope that doesn’t sound horrible.) I think there’s a middle ground here. What do you think?”

What a sweetie, right?

I thought about what we could do to make sure that this stayed as mess-free as possible. And here are a few of the guidelines that we ended up working into our agreement in order to keep our emotions in check:

Non-monogamy as an emotional buffer

My biggest downfall is that my brain wants to fuse itself to one partner, forever and always. So, incorporating non-monogamy into my sugar relationship was actually a revolutionary way for me to break that pattern. Of course, once we decided that we were going to be open, there were a couple of other questions that we needed to answer, like:

• Would we talk about other partners that we were seeing? I essentially said yes to this question because I needed that little reminder that I wasn’t my sugar daddy’s only baby.
• How would we stay safe in terms of health? No one wants to talk about sexual health, but it’s necessary. We ultimately decided that we would use protection, always, and get tested regularly.
• Would we ever be open to bringing in a third? I said no to this one because, well, jealousy. It was enough to know that my sugar daddy was seeing other people; I didn’t need to see it.

Scheduled communication (because there’s nothing sexy about a calendar invite)

I let Steve know that texting was probably too dangerous for me. What would start off as an innocent “It was nice to see you last night, what do you have planned for the rest of the weekend?” would quickly turn into me sending memes at 3 am and crashing out if I didn’t get a response. Okay, I’m exaggerating, but I know myself, and I get hooked on guys through texting.

Instead, we would schedule a one-hour video call once a week, during which we could set up our next date and then talk about anything we wanted. I honestly started to really enjoy this set-up because it almost felt more like a team meeting than a virtual date. Like, I couldn’t get swept off my feet by a calendar invite, come on.

Conversation non-starters

We also needed to keep certain conversation topics off the table, because they would inevitably end up making me fall for Steve; I just knew it. So, I told him, we should avoid:

• His childhood, his family. Sure, he could mention things about growing up, but deep dives into his upbringing were too intimate.
• His marriage. This just seemed too messy in general.
• Our romantic lives outside of sugaring. I was happy to talk about other sugar partners, but I didn’t want to hear about any person that he met on a dating app or had a crush on at work.
• Generally, personal or deep conversations. I mostly just wanted to keep things light and fun and not dive into very heartfelt or vulnerable conversations.

A monthly break-up

Okay, this one sounds weird, and it is a little bit. But basically, because we knew that there was a chance that one of us was going to develop feelings, we told each other we would take things month by month. This meant scheduling an end-of-the-month review to talk about where we were at emotionally, if we needed to make adjustments, and yes, if it was time to break up.

It became a joke between my friends and me that I couldn’t fall in love with Steve because we were only going to last one more month anyway. Maybe it sounds like dark humor, but it really did keep things in perspective for me. Like, hey, enjoy this because it’s not going to last, and that’s okay that it’s not going to last.

There were times when one of us (and not only me!) would admit that we were feeling a little bit more tender for the other person. Usually, this was around the holidays when we had to be around a lot of family members asking us if we were dating and seeing other “happy” couples on social media.

Often, just being able to talk about it allowed us to circle back to what our goals were for this relationship and whether we wanted to keep going. And month after month, we decided we did.

Eventually, Steve and I did break it off, but only because I entered into a romantic relationship with someone and felt that I could finally let my emotions run wild. We ended things on really good terms, and I even recommended him to a friend who was considering sugaring. This friend also struggled with how to navigate her feelings when dating a sugar daddy, and I told her that Steve was certainly the right kind of partner to learn those skills. Because it is a skill, and if a hopeless romantic like me can learn how to have a sugar relationship without getting swept away, anyone can!