So here’s something nobody tells you when you first start sugaring: the texting game can literally make or break your arrangement before you even meet.
I learned this the hard way during my second year in the bowl. I’d matched with this gorgeous tech exec from San Francisco—think Tesla in the garage, penthouse in Pacific Heights, the works. Our first conversation on Seeking was electric. Then I made the rookie mistake of texting him constantly once we exchanged numbers. Good morning texts. Random updates about my day. Memes I thought were funny. By day three, he’d gone completely cold.
My girlfriend Maya—who’d been sugaring way longer than me—took one look at my message thread and literally cringed. “Babe,” she said, “you’re texting him like he’s your boyfriend. He’s not. Not yet, anyway.”
That stung, but she was right. I’d fundamentally misunderstood what texting means in the sugar world versus regular dating. And honestly? Most new sugar babies make the exact same mistakes I did.
Look, Texting in the Bowl Is Its Own Language
After eight years of arrangements across NYC, Miami, and LA—and now coaching hundreds of women through their sugar journey—I can tell you that texting sits right at the intersection of professional communication and genuine connection. Get that balance wrong, and you’ll either seem desperate or ice-cold.
The thing most women don’t get initially is that successful sugar daddies are insanely busy. Like, running-multiple-companies, back-to-back-meetings, assistant-managing-their-calendar busy. My arrangement with Marcus (real estate developer, owned half of downtown Chicago) taught me this viscerally. He’d sometimes take 6-8 hours to respond to texts. At first, I spiraled—was he losing interest? Did I say something wrong?
Nope. He was literally just… working. Building empires doesn’t leave much room for constant texting.
But here’s where it gets interesting: those same men absolutely notice and appreciate thoughtful, well-timed messages that brighten their day without demanding immediate attention. Dr. John Gottman’s research on relationship maintenance shows that small, consistent positive interactions—what he calls “bids for connection”—build stronger bonds than grand gestures. In sugar dynamics, a perfectly crafted text is exactly that kind of bid.
The women who succeed long-term in this lifestyle? They master the art of being present without being needy, flirty without being cheap, and communicative without being exhausting.
Let me show you exactly how.
The Golden Rules for Texting a Sugar Daddy (That Actually Work)
Rule #1: Match his communication style, then add just 10% more warmth.
This is honestly the fastest way to get texting right. Pay attention to how he messages you:
- Does he send paragraph-length texts or quick one-liners?
- Does he use emojis or keep it professional?
- Does he text throughout the day or mainly evenings?
- Is he playful or more straightforward?
Then mirror that style—but inject slightly more personality and warmth than he does. If he’s sending brief, efficient texts, don’t respond with essays. But do add a touch of flirtiness or appreciation he might not naturally express.
Example: He texts: “Dinner confirmed for Saturday. 8pm at Cipriani.”
Don’t respond: “Ok”
Instead try: “Perfect! I’ve been dying to try their truffle pasta. Can’t wait to see you 😊”
See the difference? You matched his efficiency but added anticipation and personality.
Rule #2: The 2:1 ratio—for every text you initiate, let him initiate two.
I know this sounds like game-playing, and honestly, it kind of is. But it works because it creates natural tension and prevents you from seeming overeager. Wealthy men are used to people wanting things from them constantly. When you’re not chasing, it’s refreshing.
This doesn’t mean playing hard to get or being cold. It means being strategic about when you reach out first. Save your initiated texts for genuinely valuable moments—sharing something he’d actually find interesting, following up on something he mentioned, or sending appreciation after a date.
Rule #3: Timing is everything—respect the luxury of his schedule.
Never text before 10am unless it’s responding to him. Most successful men are deep in morning routines or already in meetings. Similarly, think twice about texting after 10pm unless you’ve established that kind of rapport.
The sweet spots? Mid-afternoon (2-4pm) when he might be between meetings, or early evening (6-7pm) when he’s wrapping up work. These are when thoughtful messages land best.
One exception: if you know his schedule. My arrangement with David (entertainment attorney in LA) worked because I knew he was a total night owl. Our best conversations happened at 11pm when his brain was still firing. But I only learned that by paying attention, not assuming.
What to Actually Text (Real Scripts That Work)
Okay, theory is great, but let’s get tactical. Here are proven text templates from my own arrangements and the hundreds of women I’ve coached:
After a great first meet & greet:
“I had such a lovely time tonight. You’re even more interesting in person than your profile suggested—which is saying something 😊 Safe travels home!”
Why this works: It’s warm, specific (referencing his profile shows you paid attention), and ends the conversation gracefully without demanding a response.
When you want to stay on his radar mid-week:
“Random thought: remember when you mentioned loving that Japanese whisky? I just walked past a liquor store with a whole rare collection in the window. Made me think of you ✨”
Why this works: It shows you actually listen to him (which is rarer than you’d think), creates a visual, and flatters him by saying he crossed your mind—without being clingy.
Following up after he sends allowance/gift:
“You just made my entire week 💕 Treating myself to that boutique I told you about tomorrow. Thank you for always being so generous and thoughtful.”
Why this works: Expresses genuine gratitude, tells him exactly how you’ll use it (men love specificity), and reinforces that you value both the gift and him as a person. Want more guidance on this crucial conversation? Check out this detailed breakdown of navigating allowance discussions.
When he’s been MIA for a few days:
“Hope everything’s going well on your end! Know you mentioned that big deal closing this week. Fingers crossed for you 🤞 Miss our conversations.”
Why this works: Shows you remember details about his life, acknowledges he’s busy without being accusatory, and gently expresses you’d like to hear from him without demanding it.
Playful/flirty check-in:
“Just got asked out by a guy at Whole Foods. Told him I was already seeing someone infinitely more interesting 😏 How’s your day going?”
Why this works: Creates mild jealousy/preselection, positions you as desirable, compliments him, and asks about him—all in two sentences. Use sparingly though; this only works if your dynamic is already flirtatious.
The Texts That Make You Look Desperate (Stop Sending These)
Real talk—I’ve seen these tank more arrangements than I can count:
The “good morning” marathon: Texting “good morning ☀️” every single day when he hasn’t established that rhythm first. It reads as desperate for attention and makes you seem like you’re sitting around waiting for him.
The interrogation: “Hey” … “What are you up to?” … “Did you see my last message?” … “Is everything ok?” within a 3-hour span. This is the fastest way to make a man retreat. If he hasn’t responded, he’s either busy or not interested—another text won’t change that.
The crisis spiral: Unloading about drama with friends, family issues, work stress, or other arrangements. Unless you’ve been together for months and he’s explicitly said he wants to be that support system, keep heavy emotional dumps off text. It positions you as high-maintenance.
I learned this one painfully. Early in my sugaring days, I texted a pot daddy this whole saga about my roommate drama. He literally responded: “Sounds stressful. Good luck with that.” We never met. Maya later explained: “He was looking for an escape from stress, and you just gave him more of it.”
The naked ask: “Can you help me with rent this month?” out of nowhere, especially before you’ve even established an arrangement. The allowance conversation should happen in person or at least after significant rapport. Random financial requests via text scream scammer or user.
The “just checking in” every 24 hours: If you have nothing specific to say, don’t text just to text. Quality over quantity always. Anthropologist Wednesday Martin notes in her research on modern relationships that “strategic scarcity” actually increases perceived value. You’re not playing hard to get—you’re being genuinely busy with your own fabulous life.
Reading Between the Lines: What His Texting Style Tells You
After years in this, I can decode a man’s texting style like a translator. Here’s what to look for:
The good signs:
- He asks follow-up questions about things you’ve mentioned = genuinely interested in you as a person
- He initiates conversations, not just responds = invested in maintaining connection
- He shares details about his life/work = trusts you and sees you as more than transactional
- He confirms plans well in advance = respects your time and is organized
- He sends the occasional unprompted compliment = thinking about you outside of logistics
The yellow flags:
- Only texts late at night = might only be looking for something physical
- Takes days to respond but is active on Seeking = you’re an option, not a priority
- Conversations always redirect to sex = probably not interested in actual arrangement
- Vague about meeting or making plans = could be a time-waster or already has someone
The red flags—run:
- Asks for explicit photos before meeting = either a pic collector or planning to ghost
- Promises large sums before meeting = classic scammer tactic
- Gets angry or pushy when you don’t respond immediately = controlling behavior, will only get worse
- Refuses to video chat or meet in public first = catfish or married guy who can’t risk being seen
For a deeper dive into identifying problematic patterns, this guide on spotting fake sugar daddies has saved countless women from wasting time.
The Advanced Move: Creating Texting Rituals That Build Connection
Once you’re in an established arrangement, texting can actually deepen your bond—if you’re strategic. The couples therapist Esther Perel talks about creating relationship rituals that maintain intimacy, and this absolutely applies to sugar dynamics.
With my longest arrangement (two years with a finance guy in NYC), we developed this thing where I’d send him a photo every Friday afternoon of whatever cocktail I was drinking to kick off the weekend. Sometimes it was at some trendy rooftop bar in Williamsburg, sometimes just my apartment. Didn’t matter. It became our thing. He’d respond with where he was, and we’d have this brief, fun exchange that kept us connected even during busy weeks.
Another successful ritual I’ve seen work: the Sunday evening recap. One of my coaching clients texts her SD every Sunday night with her “weekly wins”—three good things from her week. He loves it because it’s positive, gives him insight into her life, and takes 30 seconds to read. She loves it because it keeps her top of mind as Sunday transitions to the work week.
The key with rituals: they have to be low-pressure, positive, and consistent. Not another obligation, but something you both genuinely enjoy.
What Nobody Tells You About Texting Multiple POTs
Let’s be honest—when you’re actively seeking, you’re probably texting multiple potential daddies. This is totally normal and smart (never put all your eggs in one basket until there’s an actual arrangement). But it requires organization.
I cannot tell you how many times I almost sent a text meant for James to David or vice versa. Mortifying. Here’s what saved me:
Use contact names that include key details: Not just “John” but “John – Finance/Allergic to Shellfish/Lives in Tribeca.” Sounds excessive, but when you’re texting three Johns, it prevents catastrophic mix-ups.
Keep notes after conversations: I use my Notes app. After every text exchange or date, I write down: what we discussed, any preferences he mentioned, upcoming plans, things to follow up on. This lets you personalize messages without having to remember everything.
Never copy-paste the same message to multiple people. They can tell. Men can absolutely tell. Each person deserves a message that’s actually for them.
Be careful with voice-to-text. I once tried to text a pot daddy while getting a blowout before our first date. Voice-to-text picked up my stylist talking about another client’s “terrible extensions” and sent it. He thought I was talking about him. That arrangement never happened. Learn from my pain.
When to Take It Off Text (And Why That Matters)
Here’s something I wish someone had told me earlier: not everything should be discussed over text.
Certain conversations—negotiating allowance, addressing issues in the arrangement, defining boundaries, discussing exclusivity—need to happen voice-to-voice or in person. Text is too easy to misinterpret, screenshot, and lacks the nuance of tone and body language.
I once tried to negotiate a higher allowance over text with an SD I’d been seeing for three months. It went terribly. He got defensive, I felt dismissed, and we both misread each other’s intentions. When we finally met for dinner and had the same conversation face-to-face, we reached an agreement in ten minutes that felt good for both of us.
Research from psychologist Sherry Turkle at MIT shows that text-based communication actually reduces empathy and increases misunderstanding in emotionally charged exchanges. Keep the heavy stuff off text.
Green lights for texting: plans, light flirting, appreciation, staying in touch, sharing something fun
Red lights for texting: money negotiations, relationship problems, anything that starts with “we need to talk,” setting boundaries
The Reality Check: Sometimes He’s Just Not That Into It
Look, I have to be real with you about something uncomfortable. Sometimes, no matter how perfectly you text, a guy just… isn’t feeling it. And that’s okay.
I’ve had pots who seemed super engaged in person, exchanged numbers, then faded over text. I’ve had arrangements that were going great until they suddenly weren’t. The texting didn’t cause the fade—it was just where the fade became visible.
If someone consistently takes days to respond, gives one-word answers, never initiates, or goes radio silent, believe what they’re showing you. You can send the world’s most perfect text, but you can’t make someone interested who isn’t.
And honestly? That’s their loss. There are thousands of successful men on Seeking who will appreciate your wit, warmth, and the effort you put into thoughtful communication. Don’t waste energy chasing someone who’s lukewarm. For more perspective on navigating the early stages, here’s what to expect and how to handle first sugar dates.
Your Texting Game Plan, Starting Now
If you take nothing else from this article, remember these core principles:
Be genuinely interested, not just interesting. Ask about him. Remember details. Show you see him as a full person, not an ATM.
Add value, don’t extract it. Make him smile. Brighten his day. Make him look forward to your name popping up on his screen. That’s how you become irreplaceable.
Respect his time and yours. Quality over quantity. Thoughtful over constant.
Stay in your feminine energy. Be warm, receptive, appreciative—but also have boundaries and self-respect. Desperation repels; confidence attracts.
Pay attention to patterns, not individual texts. One delayed response means nothing. A consistent pattern means everything.
The beautiful thing about mastering texting in the bowl? It’s a skill that serves you in literally every area of life. Professional networking, friendships, all your relationships—this level of intentional communication is rare and valuable everywhere.
So go ahead. Look at your text thread with your current SD or POT. What adjustments can you make based on what you’ve learned here? Maybe it’s pulling back slightly. Maybe it’s adding more warmth. Maybe it’s establishing a fun ritual. Maybe it’s recognizing he’s not that invested and moving on to someone who will be.
Whatever it is, you now have the blueprint. The rest is just practice—and trust me, you’ll get plenty of that in this lifestyle 😊
