First Date, No Guesswork: The Playbook That Set Us Up

Whether you’re looking forward to your first-ever sugar date or a first-time meet-up with a new partner, there are a few ways that you can boost your chances of success. Let’s take a look at some guidelines from both the perspective of a sugar daddy and sugar baby so that you can know how to prepare! This is the story of Melissa and Cam.

Melissa, sugar baby

I had a good feeling about Cam from our very first online interactions. He seemed really genuine and even a little bit nerdy (he asked me what my feelings were about sci-fi fiction, bless his heart), which I liked. He instantly made me feel comfortable.

But, this is sugaring. And I had learned that even when you’re dealing with the sweetest man imaginable, it’s still important to follow some guidelines for the first date. Here’s what I mean:

Venue location

I’m not so choosy about where a sugar daddy takes me on a first date. But there are a few things that are non-negotiable for me. For one thing, it can’t be more than a thirty-minute drive from my house. Also, I won’t necessarily share my input on whether or not I like a certain restaurant choice, but I do need to know where we’re going beforehand. No surprises. That’s because I need to know what to wear, and I need to make sure it’s going to be in a public setting in a safe neighborhood.

Cam chose an upscale sushi restaurant one neighborhood over from mine, so that was perfect. The area was familiar, and I knew what to expect from the restaurant.

Dress code

I know that a lot of sugar babies may argue about this, and by all means, I think everyone should wear what they want and what they feel comfortable/sexy in. For me personally, I tend to dress smart casual for a first date, unless it’s clear that we’re going to a venue that requires cocktail attire. I never go full glam or evening wear, because it’s almost always an overshoot and makes everyone in the restaurant stare.

Basically, what I want to convey on the first date is: yes, I put a lot of thought and care into how I look. No, I’m not going to give you overly sensual on a first date, although you can bet that I will look great. Yes, my clothes are high quality, and that’s what I expect from this relationship.

For my first date with Cam, I wore a 60s style white tweed dress with cream Chanel sling-backs and a Chanel bag. I had clean makeup and my hair down. Basically, I looked classy, clean, and (I’m not afraid to admit it) beautiful, and I knew that Can was stunned when he saw me.

Communication

I’m lucky in that I have a group of girlfriends who would literally go to the ends of the earth to find me if they thought I was in trouble. And it’s always been part of my sugaring practice that I fill them in on where my dates will be, who I’ll be seeing (not overly personal details, but a basic description), and how the date is going. I let Cam know, “Hey, I hope that you don’t find this to be rude, but my protocol on a first date is to check in with my friend to let her know I’m safe when I get there and when I’m going home. Other than that, I won’t be on my phone at all.”

There’s actually another element of communication that I find important for a first sugar date, and that’s how I communicate my expectations for what the date will include. A first meet-up for me is strictly about finding out if there’s chemistry, talking about what the relationship will look like, and building some rapport. That’s it. So, I typically tell a sugar daddy that I’ll only be available for 2 hours, 2 and a half at the most, and that I plan on going home alone. This takes any guesswork or awkwardness out of it. In other words, there’s no weird “will they, won’t they” at the end of the night. And it kind of builds the excitement for the next date.

The result

You can see that my playbook for a first date isn’t so complicated. I want to know where I’m going, I want to put some thought into my outfit, and I want to stay safe by keeping in contact with friends. Everything else is based on vibes: how’s the chemistry? Are there any red flags? How does he react when we talk about the terms of the relationship? And with Cam, everything was very easy. But I’ll pass it over to him to see what his guidebook looked like.

Cam, sugar daddy

I don’t think that Melissa knew this at the time, but she was my first sugar baby. So, I was a little bit in the dark when it came to having guidelines or etiquette for a first date. I read what she had sent me, about the venue and other details, and I thought to myself, “Okay, if I were in her shoes, how would I want a sugar daddy to treat me?” And so I came up with my own list of “rules” that I would follow:

Venue

Melissa said that she wanted something not too far from home, but didn’t have any specific requests. So, I decided that I should come up with a set of guidelines for myself for this and future dates. I wanted to choose a place that was upscale without being so stuffy that either of us would feel uncomfortable on a first date. Good reviews. A kind of food that was light enough that we didn’t feel sluggish afterwards. And something that would pair with good wine. I settled on sushi with Melissa, but I could have easily chosen New American Cuisine or Tapas.

Transportation

I wanted Melissa to feel taken care of for the entirety of the date, and that meant arranging transportation for her. For safety reasons, she wanted to book her own ride, which I totally understood. So, I transferred the money to her ahead of time for both the trip to and from the restaurant. That way, she wouldn’t feel like she needed to ask me for more cash when she was ready to leave.

Basic etiquette

I’ve always been a bit of a traditionalist when it comes to dating etiquette. And sugar dating is no different. So, I made sure to check in with Melissa the day before our date to make sure she would still be available. I showed up fifteen minutes before her just to be 100% sure I would get there first. I had a small gift for her, and I let her know right away how beautiful she looked. Throughout the evening, I made her needs my priority. We ordered the sushi rolls that she liked, and I always made sure that her glass was filled, anything she needed.

Follow-up

Melissa and I had an excellent first date. It was clear that there was chemistry and that we were both serious about being a good partner to one another. But I knew that the ball was in my court to make sure that we had a second date, and a third, and however many after that.

First things first, I made sure she got home okay. And then, I didn’t let the conversation go on unnecessarily. I told her that I was glad to hear she was safe and that I had a great time, and then I bid her goodnight.

The very next day, I reached out again to ask whether she would have any availability over the next week for a second date. No dating games, just direct communication. And I think she responded really well to that. It showed that I was serious and confident.

Back to Melissa

I had a feeling that I was Cam’s first sugar baby, but that wasn’t a problem for me because he made such an effort to be thoughtful. And that’s all it really is. Everyone’s guidebook is going to be different. There are going to be things that you think are important that another person may not be so strict about. But the important thing is that you do think about what’s important and create a set of dos and don’ts for your own sugaring experience. That being said, everyone’s playbook should include something about safety, basic decency, communication, you know, the basics.

And if you’re lucky, you’ll find your version of Cam. Because he was thoughtful, he definitely landed himself a second (and third, and what are we on now, fortieth?) date.