Look, I’m gonna be honest with you—after eight years in the bowl and countless conversations over champagne at The NoMad and quiet corners of Catch LA, I’ve developed what I call my “bullshit radar.” And honey, it’s finely tuned.
My third arrangement almost derailed my entire perspective on sugar dating. He was a hedge fund guy from Greenwich—impeccable on paper, charming at our first meet at Balthazar. But within two weeks, I was walking on eggshells, second-guessing every text, rearranging my entire schedule around his unpredictable moods. The allowance was generous, sure, but I felt like I was constantly auditioning for a role I’d already been cast in.
That’s when I learned the most expensive lesson of my sugar baby career: red flags don’t get better with time—they just get more expensive to ignore.
Here’s what nobody tells you when you’re starting out: red flags aren’t always dramatic. They’re not always the guy who shows up drunk or asks for nudes before you’ve even met. Sometimes they’re subtle—a comment that makes you pause, a pattern you can’t quite name, a feeling in your gut that something’s… off.
Dr. John Gottman, who’s studied thousands of couples over decades, says that contempt is the single greatest predictor of relationship failure. And guess what? That applies to arrangements too. The way someone treats you when they think you need them more than they need you? That tells you everything.
So let’s talk about the 20 red flags I wish someone had spelled out for me before I wasted six months on arrangements that were never going to work—no matter how good the allowance looked.
1. His Communication Pattern Feels Like a Slot Machine
You know what I mean—sometimes he’s texting you paragraphs at 2am, other times you’re left on read for three days straight. There’s no predictable rhythm, no consistency you can rely on.
I dated a tech founder in San Francisco who did this. When he was between funding rounds, I’d hear from him constantly. The second he closed his Series B? Radio silence for a week, then he’d resurface like nothing happened with “Hey beautiful, miss you.”
Here’s the thing: inconsistent communication isn’t about being busy—it’s about not prioritizing you consistently. Rich men are busy, yes. But they’re also extremely good at managing what matters to them. If he can respond to his investors within an hour but leaves you hanging for days, you’re not in his priority column.
What consistency should look like: A quick “Slammed today but thinking of you” text takes 10 seconds. That’s the bare minimum of respect.
2. He Needs to Know Where You Are. Always.
There’s a difference between “How was your day?” and “Where are you right now? Who are you with? Send me a photo.”
I once had a potential SD who, on our first date at Carbone, casually suggested I share my location with him “for safety.” When I politely declined, he got visibly uncomfortable and spent the next twenty minutes explaining how “his last sugar baby loved that he cared so much.”
Yeah, we didn’t have a second date.
Look, protective is one thing. Possessive is another. And the guys who blur that line early on? They’re not going to magically respect your boundaries later when there’s money and intimacy involved.
Your independence isn’t negotiable—it’s the foundation of a healthy arrangement. Any man who makes you feel like you need to justify your time or whereabouts before you’ve even established exclusivity is waving a red flag the size of Texas.
3. The Allowance Conversation Keeps Getting Postponed
“Let’s just see how things go first…”
“I want to make sure we’re compatible before we talk numbers…”
“Don’t worry, I’ll take care of you…”
Girl. No.
I learned this the hard way with a real estate developer in Miami. Three dates in, including an overnight trip to the Keys, and we still hadn’t discussed actual terms. He kept saying he “wasn’t transactional” and wanted things to “develop naturally.” Know what developed naturally? Me feeling used and him acting shocked when I finally brought it up.
Anthropologist Wednesday Martin, who studied wealthy communities extensively, notes that transactional clarity actually strengthens relationships by removing ambiguity. And that’s exactly what the allowance talk does—it creates clear expectations.
A real sugar daddy isn’t afraid to discuss terms because he values transparency. The guys who dodge this conversation? They’re either not financially stable enough to be SDs, or they’re hoping to get the benefits without the responsibilities.
4. He’s Pushing for Intimacy Before You’re Comfortable
This should be obvious, but I’ve seen too many smart women ignore this because “the allowance is really good” or “he’s been so generous already.”
Your comfort timeline isn’t up for negotiation. Period.
I remember a POT in Chicago who kept steering every conversation back to sex—what I liked, what he wanted to do, when we could “really get to know each other.” Meanwhile, we’d met twice for coffee. When I suggested we have a few more public dates first, he actually said: “I don’t have time for this. I thought you were serious about an arrangement.”
Yeah, that tells you everything you need to know about what he values.
The right SD understands that genuine connection requires patience. He’s not auditioning you for a role—he’s getting to know a whole person. And if he can’t respect your pace? He’s not going to respect much else either.
5. His Personal Life Is Classified Information
Some discretion? Totally normal. Complete opacity? That’s different.
You don’t need his social security number, but you should know basic facts: Is he married? (Many are, and that’s fine if everyone’s honest.) What does he actually do for work? Does he have kids? What city does he primarily live in?
I once met a guy who wouldn’t tell me his last name until our fourth date. Wouldn’t say what company he worked for, just “finance.” Wouldn’t even mention what neighborhood he lived in beyond “Upper East Side.” When I finally Googled him after he slipped up, turns out he was married with three kids—and his wife was very publicly active in Manhattan social circles.
The problem wasn’t the marriage (I’ve had transparent arrangements with married men). The problem was the deception.
Secrecy and discretion are not the same thing. Discretion protects everyone involved. Secrecy usually protects him while leaving you vulnerable.
6. His Mood Swings Keep You Guessing
One dinner he’s warm, engaged, making plans for next week. The next time you see him, he’s cold, distracted, irritable—and you have no idea what changed.
This was my reality with an entertainment exec in LA. Our dates felt like emotional roulette. Sometimes I’d show up to The Tower Bar and he’d light up the room, introducing me to everyone, ordering my favorite champagne. Other times—same restaurant, same me—he’d barely make eye contact, spend half the dinner on his phone, and end the evening early with a vague “I’ll text you.”
I spent so much energy trying to figure out what I’d done differently. Spoiler: it wasn’t about me.
Dr. Brené Brown talks about how “clear is kind, unclear is unkind”—and unpredictable emotional availability is the ultimate unkindness. It keeps you in a constant state of anxiety, always performing, never secure.
You deserve emotional consistency, not a relationship that feels like a psychological experiment.
7. The Way He Talks About Women Makes You Uncomfortable
Pay attention to how he describes his ex-wife. His previous sugar babies. Women in general. The server at the restaurant. His assistant.
Is there a pattern of contempt? Does he use terms like “crazy” or “gold digger” casually? Does he make comments about women’s appearances in ways that feel reductive?
I once had a meet-and-greet at Sant Ambroeus where the guy spent twenty minutes complaining about his “psycho ex-wife” who “took him to the cleaners.” Then he pivoted to rating the attractiveness of every woman who walked by. Then he told me I was “smart for a sugar baby.”
I finished my cappuccino and politely excused myself. Because here’s what I’ve learned: how he talks about other women is how he’ll eventually talk about you.
The contempt might not be directed at you now. But contempt is a habit, and habits spread.
8. Promises Evaporate Like Morning Fog
“I’ll send the allowance Monday.” (It’s Thursday.)
“Let’s plan that trip to Tulum.” (Never mentioned again.)
“I’ll help you with that business idea.” (No follow-through.)
Broken promises are death by a thousand cuts in sugar arrangements. Each one individually seems small enough to overlook, but collectively they erode trust until there’s nothing left.
I had an SD who promised to help me with setting up my business accounts properly—he was in private wealth management, so I was excited for the guidance. He brought it up, not me. But every time I followed up, he had an excuse. Eventually I stopped asking, and he never mentioned it again.
Small thing? Maybe. But it taught me he said things to make himself feel generous without any intention of following through.
Consistency between words and actions is the foundation of trust. Without it, you’re building on sand.
9. Your Independence Threatens Him
He gets weird when you mention drinks with friends. He questions why you need hobbies outside of seeing him. He makes subtle comments about your career ambitions like “Why work so hard when I take care of you?”
This is control disguised as care.
I watched a friend’s arrangement deteriorate because her SD couldn’t handle that she was building a successful lifestyle blog. He’d make passive-aggressive comments about her “spending so much time online” or suggest she didn’t need to “hustle so hard.” But she loved that blog—it was hers, independent of him.
Eventually he gave her an ultimatum: the blog or the arrangement. She chose the blog. Two years later, she’s turned it into a six-figure business, and he’s still cycling through sugar babies who make him feel important.
The right man celebrates your independence because he’s secure enough not to need you dependent. Insecurity wears a lot of masks—possessiveness is just one of them.
10. Everything Happens Behind Closed Doors
If six months in you’ve never been to a restaurant, never attended an event together, never done anything that involves other human beings seeing you as a couple… that’s telling.
Now, discretion is understandable. Married SDs need to be careful. I get that. But there’s a difference between being thoughtfully discreet and treating you like a secret he’s ashamed of.
I once had an arrangement where we only ever met at his apartment. Nice place—Central Park West, stunning views—but after three months I started feeling like a houseplant. When I suggested meeting for dinner somewhere, anywhere, he deflected. Too recognizable, too risky, his schedule was complicated.
But you know what? He found time to be “seen” plenty in his professional life. The issue wasn’t visibility—it was visibility with me.
You deserve to exist in the same world he moves through, even if it requires creativity to navigate discretion. Being someone’s secret isn’t the same as being in a discreet arrangement.
11. His Financial Stability Seems… Questionable
He drives a leased Maserati but complains about his rent. He wears a Rolex but his credit card gets declined at dinner (happened to me—awkward as hell). He talks about deals that are “about to close” but never seem to close.
Look, I’m not saying you need to run a credit check. But there should be consistency between his lifestyle claims and observable reality.
The LA entertainment industry is full of guys who look wealthy—right car, right watch, right restaurants—but are actually leveraged to their eyeballs and one bad quarter from a financial crisis. I learned to spot the difference between actual wealth and performed wealth, and let me tell you: actual wealth is usually quieter.
My most generous SD? Drove a five-year-old Mercedes, wore a $200 watch, and never felt the need to announce his net worth. But he owned properties in three cities, never blinked at allowance, and once casually bought me a laptop when mine crashed—didn’t even want me to pay him back.
The guys doing the most talking about their money? Usually have the least of it.
12. Generosity Comes With Strings Attached
“After everything I’ve done for you…”
“I bought you that bag, so…”
“Remember when I helped you with rent?”
Transactional clarity is healthy. Using generosity as emotional leverage? That’s manipulation.
I experienced this with an SD who’d bring up his gifts or allowance whenever we had any disagreement. Not even big conflicts—just normal “I’d prefer to meet Thursday instead of Friday” type stuff. He’d respond with reminders of his generosity, like that changed whether my preference was valid.
Real generosity doesn’t come with an emotional invoice. If he’s keeping a mental spreadsheet of everything he’s done and pulling it out whenever you assert a boundary, that’s not generosity—that’s control with a price tag.
13. He’s Not Curious About Your Actual Life
Ask yourself: Could he name three of your actual goals? Does he know what you’re studying? What you want to build? What lights you up?
Or does every conversation center back on him—his day, his stress, his needs, his interests?
The arrangement that taught me the most was with a venture capitalist who asked me about my business ideas like he actually cared about the answers. He’d follow up weeks later: “How’s that online course coming along?” He introduced me to people who could help. He celebrated my wins.
That’s what mutual investment looks like. And it doesn’t matter how generous the allowance is—if you’re not being seen as a full person with your own dreams, you’re being treated as an accessory.
You bring more to an arrangement than companionship and beauty—and the right SD knows that.
14. Alcohol or Substances Are a Third Party in Every Interaction
A few drinks over dinner? Normal. Needing to be drunk to function socially? That’s different.
I’ve dated high-achieving men who use alcohol to wind down from intense careers—that alone isn’t a red flag. But if he can’t get through an evening without being noticeably intoxicated, or if his personality completely changes after a certain number of drinks, pay attention.
And if substances beyond alcohol are regularly part of the picture—especially if he’s encouraging you to participate when you’re not interested—that’s a boundary issue waiting to explode.
Safety first, always. You can’t have a healthy arrangement with someone who’s regularly not fully present.
15. His Story Keeps Changing
First he said he’s divorced. Then he’s “separated.” Then actually his wife knows about arrangements. Then actually they’re working on things…
Or his job title shifts every time he mentions it. Or the timeline of when he moved to New York doesn’t add up. Or basic facts just don’t stay consistent.
Look, memory isn’t perfect. But when core facts about someone’s life keep shifting, you’re either dealing with a pathological liar or someone who’s hiding something significant.
Neither is a good foundation for an arrangement built on trust.
16. He Wants Exclusivity but Offers Nothing Comparable
“I don’t want you seeing anyone else” + “I’m not looking for anything serious” = math that doesn’t work.
Exclusivity is a two-way street. If he wants you to be exclusive—no other arrangements, no vanilla dating—he needs to offer commitment that matches. Higher allowance, more time, genuine investment in the relationship.
I once had a POT suggest I pause my Seeking account after two dates. When I asked what he was offering in exchange for exclusivity, he looked confused. “I just don’t like to share,” he said.
Cool story. I like to be compensated fairly for what I’m offering. We weren’t a match.
Your exclusivity has value—make sure it’s valued appropriately.
17. Every Ex Was “Crazy”
If every woman in his past was crazy, manipulative, a gold digger, or psycho… chances are the common denominator isn’t them.
One bad relationship? Sure, happens to everyone. A pattern of “crazy exes”? That’s a guy who doesn’t take responsibility for his role in relationship dynamics.
Dr. Esther Perel, the renowned couples therapist, often notes that how people talk about past relationships reveals how they’ll eventually talk about you. The contempt he shows toward women in his past is contempt that will eventually find its way to you.
Listen for accountability when he discusses past relationships. “We weren’t compatible” is very different from “She was insane.”
18. He’s Rushing Everything
Wants to lock in an arrangement after one coffee. Pushing for intimacy on the first date. Talking about exclusivity before you’ve established basic compatibility.
Speed isn’t the same as enthusiasm. And when someone’s trying to lock you down before you’ve had time to assess whether this is actually right for you, ask yourself: what’s the rush?
Usually, it’s because they’re afraid if you take time to think, you’ll realize this isn’t what you want. Or because they’ve been through so many sugar babies that they’ve commodified the whole process—just want to get to the “good parts” without building actual connection.
The right arrangement can handle a little time and patience. If he can’t, that tells you something.
19. Your Boundaries Are Suggestions to Him
You said you’re not comfortable with last-minute plans, but he keeps texting “You free in an hour?”
You mentioned you don’t like certain intimate activities, but he keeps “forgetting” or pushing.
You asked for more notice before he visits your city, but he shows up expecting you to drop everything.
This isn’t forgetfulness. This is testing to see what he can get away with.
Boundaries aren’t negotiable. They’re information about what makes you feel safe and respected. A man who repeatedly “forgets” your boundaries is a man who doesn’t respect them—or you.
20. He’s Emotionally Unavailable But Wants You Available 24/7
He expects you to be responsive, emotionally supportive, understanding when he’s stressed—but when you need reassurance or connection, he shuts down or goes distant.
This is probably the most exhausting dynamic I’ve experienced in the bowl. The SD who wanted all the emotional benefits of a relationship—someone to vent to, someone to make him feel special, someone to soothe his ego—but who went cold the second I needed anything resembling emotional reciprocity.
One guy actually told me: “I’m paying for an escape from emotional complications.” Cool, but guess what—I’m a human being, not a fantasy dispensing machine.
You can’t have a one-way emotional arrangement where all support flows toward him. That’s not sugar dating—that’s emotional labor with a paycheck.
So What Do You Actually Do With All This?
Here’s the thing nobody tells you: recognizing red flags is actually the easy part. The hard part is acting on them when the allowance is good, when you’ve already invested time, when he’s not terrible all the time.
I’ve stayed in arrangements months past their expiration date because I kept thinking “maybe it’ll get better” or “it’s not that bad.” You know what I learned? Red flags don’t age like wine. They age like milk.
My approach now: I give one clear conversation per red flag. If something bothers me, I address it directly: “Hey, I’ve noticed [specific behavior]. Here’s why it doesn’t work for me. Can we adjust this?”
His response to that conversation tells me everything I need to know. Does he:
- Listen, acknowledge, and change the behavior? Green flag.
- Get defensive, turn it around on me, or make excuses? Red flag confirmed.
- Agree in the moment but nothing changes? Red flag in action.
And if it’s a safety issue—controlling behavior, boundary violations, anything that makes you feel unsafe—you don’t owe him a conversation. You don’t owe him an explanation. You owe yourself protection.
I also keep what I call a “reality check doc” in my phone. Any time something feels off, I write it down with the date. You’d be surprised how helpful this is when you’re tempted to gaslight yourself with “maybe I’m overreacting.” Patterns become obvious when you can actually see them documented.
And look—I want to be clear about something. Recognizing these red flags doesn’t mean sugar dating is toxic or dangerous. It means you’re going into it with your eyes open, with standards, with self-respect.
I’ve had arrangements that enriched my life in ways I’m still grateful for. I’ve met fascinating men who treated me with genuine respect and invested in my growth. I’ve learned things about business, about people, about myself that I wouldn’t have learned anywhere else.
But those beautiful experiences happened because I got better at spotting and avoiding the situations that weren’t serving me. The arrangements that worked were with men who didn’t exhibit these red flags—or who, when something came up, were willing to address it like adults.
Your instincts are smarter than you think. If something feels off, it probably is. You don’t need to be able to articulate exactly why in that moment—trust the feeling first, analyze it later.
And remember: no allowance is worth your peace of mind, your safety, or your self-respect. There are generous, respectful men out there looking for genuine arrangements. Don’t settle for less because you’re afraid there’s nothing better.
Because there is. I promise you, there is.
