New year, new dating style. Courtesy of a former sugar baby.
Being a sugar baby had its (obvious) perks, but the most significant ones didn’t center around the material benefits. To date, I have a bigger appreciation for the lessons I’ve learned and applied them to my dating life.
Dating men of higher social status shortened my tolerance for a lot of things I was convinced were normal. I blamed the universe for attracting undesirable men when it was my fault for allowing undesirable behavior. An interesting dichotomy between those guys and sugar daddies was the treatment I accepted.
It was easier to put my foot down with men of opulence because their privilege meant there was no limit to meeting my desires. Plus, recognizing my own worth made them (the good ones) want to treat me with the same high regard.
I’ll admit you don’t NEED to be an SB to enhance your dating style, but that’s the path I journeyed. It taught me how to be gracefully tough on men based on the simple fact that I’m invaluable. I’ll never convince anyone to be an SB, but feel free to pick a few gems I learned that might take your 2025 dating style to the next level.
Don’t overdo it by showing gratitude.
Let’s stop praising men for the bare minimum.
Yes, it’s okay to make a man feel affirmed but don’t let those affirmations come off too intensely, especially for things that require minimal effort. Don’t tell him about your ex never opening the passenger door for you, don’t brag about him being "The One" because he texted to make sure you got home safely, and most definitely don’t offer up the cat just because he paid a $150 dinner bill (give it because you want to, not out of obligation).
To be honest, I barely even say thank you when a man finds me attractive. “You are so beautiful.” I would respond, “Aww, you’re so sweet.” When he holds the door open, I graze his arm and smile.
Showing too much excitement about the bare minimum strokes his ego and draws a ceiling, which he doesn’t feel he needs to surpass. It tells him you’re not used to regular treatment, so you’ll be grateful for anything. Why do more than necessary? I like my men reflecting at the end of our date, thinking, “What can I do to impress her?”
Don’t stop having manners, though. Just keep it simple and move on.
There’s no such thing as “dating for potential.”
Hold my hand with this one.
There comes a time when the word “potential” shouldn’t be a part of your dating vocabulary. It’s nothing more than the encouragement of false hope. He’s not flaky with time because his schedule is too busy between balancing family and work. It’s because you’re not important enough to prioritize making time for.
He’s not stingy on dates because he’s having a rough time handling all his financial responsibilities. It’s because he’d rather spend his money on things that don’t involve you.
Trust me when I say men don’t date with potential in mind. Many of them hold themselves in very high regard with an “I can do better” mindset, and so should you. There’s A LOT of weight in the saying, “If he wanted to he would.” So stay away from Mr. Shoulda Coulda Woulda because, at the end of the day, he didn’t.
*P.S. If he ever says he doesn’t deserve you, he’s not being sheepishly humble. Take his word for it and run.
Do NOT be afraid to say no.
How many times have you put yourself through something you didn’t want to do based on feeling obligated? You compromised yourself in order to please the person you’re dating because it seemed like the easier option. Let me just remind you of the old saying, “Nothing good in life comes easy.”
I like comparing men to children, not to demean them but to draw similarities. Children often like to push and see how much they can get away with until the parent says no. Once you allow them to get away with one thing, they’ll nudge the limits to see how often they can skate by.
Dating is just like this. Get comfortable giving rejection. It can be an uncomfortable concept for some, so consider saying no and following it with a light reason. For example, “Do you want to come over and watch Netflix?” “No, I don’t feel comfortable going to strangers’ houses.” If his response is anything but understanding with a Plan B, on to the next.
Those boundaries were created to protect you. Any man who respects you will respect them too.
Don’t lay all your cards on the table.
When a man asks, “So what exactly are you looking for?” The vaguest response comes to mind.
It’s a common mistake to think men (not all) ask questions for unselfish reasons. That one, especially, is basically like asking for cheat codes to a game. Describing your idea of a perfect man, dating intentions, etc. allows him to know who he needs to morph himself into in order to get what he wants. Enter love bombing, physical intimacy, delusions of potential, then ghosting.
I’ve said the below on a few first dates and wasn’t surprised by how quickly the guys weeded themselves out.
"I’ve been having fun figuring things out as time goes on. There are times when I love going out to meet new people and times when I love cuddling up on the couch. It depends on how I’m feeling.”
I just said a whole lotta nothing, leaving it up to him to decipher. It’s open-ended, which forces him to show his intentions and let things play out naturally with as little manipulation as possible.
The first date defines how he views you.
This is where all those conversations leading up to this day come into play.
The perfect first date doesn’t only have to consist of 5-star dining and lavish wine collections. Those are merely perks. The perfect first date is valued based on how much effort he put in to show he’s been listening.
You’ve been dropping subtle hints that tulips are your favorite flowers. Did he show up empty-handed? You shared your discomfort with driving to far places at night. Did he book a 9 p.m. reservation somewhere 30 minutes away? You told him about your new venture into veganism. Did he take you to his favorite steakhouse?
These aren’t small things and they’re DEFINITELY not things for you to take on as a challenge. These could be easy signs of a life full of selfishness and laziness if shrugged off by the belief you should be satisfied with him making time for you.
Will taking my advice find you a husband faster? Who knows? But, ultimately, dating isn’t supposed to be an earnest search for a man. It should be a time of personal growth while sorting through experiences to find a partner who will appreciate the valuable woman you are.
Having high standards for yourself doesn’t make you difficult or unreasonable. To the right man, it definitely won’t make you undateable. Like I said before, nothing good in life comes easy.
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Skylar sees things differently. At the time, she was shooting content on her iPhone. Temi came into the picture with a new perspective, an understanding of tech, and, eventually, a camera. “He doesn't give himself enough credit,” Skylar says. “He wasn't just my tripod. He wasn't just standing behind the camera and going ‘click.’ He was giving advice. He was giving me insight to how I could look at things from a different perspective. And I was like, 'Oh, he’s an artist.' I think it was maybe a heartbeat of that kind of energy of like, ‘Baby, can you take this picture?’ And it turned so quickly into, we're partners. We can work together in a way where we're advancing each other's creative thinking.”
The pair often says they’re two sides of the same coin. Skylar is an Aquarius. She attended art school, paints, and loves poetry. She’s more than happy to let the couple’s management firm and agency, Kensington Grey, handle their admin work. And, she loves to sleep in. Temi, on the other hand, wakes up early. He’s a Virgo. He loves a to-do list and regularly checks in on the couple’s brand partnerships spreadsheet to make sure everything is on track.
Because his storytelling was steeped in his love of technology, he didn’t always think of himself as a creative person. “Where I [am] the dreamer who wants to pluck things out of the sky and spend all day with my head in the clouds, Temi [is] so good at grounding me and helping me figure out how to make things make sense on paper. We just work together in such a complimentary way,” Skylar says.
It’s been more than six years since Brooklyn-based couple Temi and Skylar started dating, and nearly four since they cemented their working relationship. On TikTok and Instagram, the couple’s travel, fashion, and home content regularly rack up hundreds of thousands of views. They’ve worked with brands such as Coach, Aesop, Away, and Liquid IV, bringing their vibrant perspectives to every campaign they execute. Still, nearly two years since both Temi and Skylar committed to full-time content creation and creative directing, the couple says their romantic connection remains their priority.
“We told each other we would much rather go back to full-time jobs and preserve our relationship than to be full-time freelancers, barely getting a night's rest [and] barely kissing each other because we're so busy shooting,” Skylar says.
Working from home can make it hard to separate work from personal life for any entrepreneur. It can be even more challenging when your business partner is also your lover. Temi and Skylar had already used couples therapy as a tool to help them effectively communicate with one another. When they ran into challenges while working together, their therapist helped them set physical boundaries to help combat the issues.
"We told each other we would much rather go back to full-time jobs and preserve our relationship than to be full-time freelancers, barely getting a night's rest [and] barely kissing each other because we're so busy shooting."
“It actually took us doing very specific physical things to create boundaries between work and play in our relationship,” Skylar says. “So, for instance, we will only have conversations about work when we're out of bed or we're at the table or in the office. Initially, when we started, we had to light a candle to say that, 'Okay, this is a space where we're connecting, we’re not talking about work.' We needed really hard boundaries at the top. And then it became a little bit more organic.”
The boundaries have been crucial to implement, especially because the couple began working together so naturally. When the pair first met, Skylar was NY-based a social strategist for BuzzFeed and was using content creation to drive business to her lingerie company. She was shooting her own content. Temi was working for Microsoft in D.C. He’d recently traded in his DJing equipment for a camera. “I've always loved taking pictures,” he says. “Even when I was a kid, my African mother would wake me up at 3:00 a.m. [during a] party, and be like, 'Come take the family picture.'”
Growing up, Temi says he watched his parents support each other and be the true definition of partners. He knew he wanted the same for his own relationship. But, the couple also wanted to make sure they were being financially responsible. The pair didn’t quit their traditional jobs until they’d saved up two years' worth of their cost of living. And, Temi received his Master of Business Administration from New York University with the knowledge that it could either help him advance in his corporate career or be applicable to his business with Skylar.
Temi and SkylarCj Hart @hartbreakToday, they say their working relationship is more of a “quiet dance.” They still implement some of the boundaries they learned in therapy, but they also lean into their natural strengths and deep love for one another. When we speak, Temi has planned a date for the couple to see Princess Mononoke in 4K IMAX and added it to their Notion so they can factor it into their busy schedules. “I fully plan to date for the rest of my life,” he says.
Skylar says the couple doesn’t just wait for date nights to check in with one another, though. This often happens in the mornings, after Temi has made her peppermint tea and poured himself a cup of coffee. When they ask each other how they slept, she says, it’s not just a “nicety.” It’s a genuine question meant to foster connection.
“A lot of it happens during the day in the midst of work. We'll stop and we'll hug. Or we’ll slow dance in the kitchen,” she says. “Sometimes it's hard to set a whole date night when you have 7,000 things going on. So, we must grasp these moments and check in when we can. And I think it's become so organic to us that I actually didn't even realize how often we do it. But all day long, we're like, 'Are you good? I felt like your energy shifted,' because we're best friends, we just know. We just feel it happen.”
What’s better than being in love? Building wealth while doing it. Watch Making Cents here for real stories of couples who make money moves together.
Featured image by Cj Hart @hartbreak