So there I was at Balthazar in SoHo, second date with a hedge fund guy who’d been nothing but decisive about everything—the reservation, the table placement, even which side of the booth I should take. Then the wine list arrived, and he slid it across the table with this expectant smile: “You choose.”
I froze.
Look, I’d been in the bowl long enough to handle most curveballs, but wine? That leather-bound tome of French regions and vintage years might as well have been written in hieroglyphics. I remember thinking, is this a test? Does he want to see if I know the difference between Bordeaux and Burgundy? Or is he genuinely just being nice?
That moment taught me something crucial about sugar dating dynamics that nobody talks about: it’s rarely about the wine. It’s about how you handle uncertainty, communicate your boundaries, and collaborate with someone who operates in a completely different world than you might be used to.
After eight years and more wine lists than I can count across NYC, Miami, LA, and everywhere in between, I’ve cracked the code on this particular scenario. And honestly? Once you understand what’s really happening in this moment, it becomes one of the easiest ways to build genuine connection with your SD.
Why He’s Really Asking You to Choose (It’s Not What You Think)
Here’s the thing most sugar babies get wrong: they assume it’s a test of sophistication. That he’s sitting there mentally scoring them on whether they can pronounce “Châteauneuf-du-Pape” correctly.
Bullshit.
In my experience with successful arrangements—and I mean the ones that lasted years, not weeks—quality men do this for entirely different reasons:
He wants to see your personality come through. A tech founder I dated in San Francisco once told me he’d rather watch a woman confidently order the house red because she genuinely liked it than hear someone parrot sommelier-speak they clearly Googled five minutes earlier. Authenticity trumps pretension every single time with men who’ve seen it all.
He’s creating space for you in the dynamic. Look, there’s already an inherent power imbalance in sugar relationships—he’s providing financial support, which naturally puts him in a position of control. Thoughtful SDs recognize this and deliberately create moments where you lead. It’s not charity; it’s him investing in making the arrangement feel balanced.
He genuinely wants to know what you like. Mind-blowing concept, right? But some men actually enjoy discovering their SB’s preferences. I had an arrangement with a real estate developer in Miami who kept notes on his phone about which wines I’d enjoyed at different restaurants. That’s the level of attentiveness that separates arrangements from transactions.
According to Esther Perel, renowned couples therapist and author of Mating in Captivity, “Desire needs space to thrive. When one partner always leads, the other becomes passive—and passivity kills attraction.” She’s talking about traditional relationships, but it applies ten times over in the bowl where power dynamics are even more pronounced.
But here’s where it gets tricky: he might also be fucking lazy or testing whether you’ll take initiative in other areas of the arrangement. Not every SD who does this has pure motives, and part of navigating the bowl successfully is reading which category your date falls into.
The Anatomy of a Wine Panic (And Why It Happens to All of Us)
Let me paint you a picture of what goes through most sugar babies’ heads in this moment, because I’ve been there and I’ve coached dozens of women through it:
You’re already managing multiple calculations during dinner—does he seem engaged? Is the conversation flowing? Did I strike the right balance between interesting and available? Is my lipstick still perfect? Then suddenly you’re handed a wine list that looks like a phone book, and your brain short-circuits.
The internal monologue goes something like:
“Okay, don’t panic. Red or white? What are we eating again? Shit, I should’ve paid attention when he ordered. Is that Pinot Grigio or Pinot Noir? Why are there so many French words? The most expensive one is $800—is that a reasonable price or insane? If I choose something cheap, will he think I’m not sophisticated? If I choose something expensive, will he think I’m using him? Oh god, he’s watching me. Say something. SAY SOMETHING.”
And then you blurt out whatever your eyes land on first, or worse—you freeze completely and hand it back with some self-deprecating comment about not being a “wine person.”
I get it. The performance anxiety is real, especially early in an arrangement when you’re still figuring out the dynamics and establishing boundaries.
But here’s what I learned the hard way: the women who thrive in the bowl aren’t the ones who know everything—they’re the ones who know how to handle what they don’t know with grace.
The Scripts That Actually Work (Tested in Real Life)
Alright, let’s get practical. I’m giving you the exact approaches I’ve used and taught that turn this potentially awkward moment into a connection opportunity.
The Confident Collaborative:
“You know what? I’d love your input on this. I’m between the Malbec and the Cabernet—which do you think would pair better with what we ordered?”
Why this works: You’re showing initiative by narrowing options, but inviting his expertise without completely deferring. It’s collaborative, not helpless. I used this approach at Catch LA with an entertainment industry SD, and it led to a 20-minute conversation about Argentine wine regions that was genuinely fascinating.
The Playfully Honest:
“Full transparency? I know cocktails way better than wine. But I’m always up for trying something new—surprise me with something you think I’d like based on what you know about me so far.”
Why this works: Honesty wrapped in confidence is incredibly attractive. You’re admitting a knowledge gap without apologizing for it, and you’re giving him an opportunity to demonstrate thoughtfulness. Plus, how he responds tells you a lot about his character.
The Decisive Move:
(After a quick scan for anything you recognize) “Let’s do the Sancerre. I had something similar at [insert real place if you can, or just say ‘a friend’s dinner party’] and loved it.”
Why this works: Decisiveness is underrated. Even if it’s not the “perfect” choice, making one confidently demonstrates you can handle pressure. I once ordered a wine I’d literally never heard of at The Grill in NYC purely because the name sounded pretty—turned out to be exceptional, and my SD was impressed by the boldness.
The Sommelier Redirect:
“Honestly, this menu is impressive—let’s get the sommelier’s recommendation for what we’re having. I find they always have great insights.”
Why this works: You’re taking control by delegating to an expert, which is actually what smart people do in high-stakes situations. Any SD worth his salt will respect this move because it’s exactly what he does in business—bring in specialists when needed.
Here’s what you should never do: Immediately push it back with “Oh, I couldn’t possibly choose” or “You’d be better at this than me.” That’s not humility—it’s diminishing yourself, and it sets a precedent that you’re uncomfortable with agency in the arrangement.
Building Your Wine Confidence (Without Becoming a Sommelier)
Look, I’m not about to tell you to take wine courses or memorize French regions. But if you’re going to be dating men who frequent places with serious wine programs, knowing a few basics will serve you well—not to impress them, but to feel comfortable navigating these situations.
Here’s my crash course based on what’s actually useful in sugar dating contexts:
Know Your Personal Baseline
Figure out what you genuinely like—not what you think you should like. Do you prefer lighter, crisper wines or fuller, richer ones? Fruity or earthy? I discovered early on that I love New Zealand Sauvignon Blanc and Oregon Pinot Noir, and I’ve ordered variations of those confidently for years. That foundation makes everything else easier.
Pro tip: When you’re out with girlfriends or on casual dates, actively pay attention to what you’re drinking. Take notes on your phone if needed. Building your preferences doesn’t require expensive tastings—just mindfulness.
Learn the Foolproof Pairings
- Seafood/light fish: Sauvignon Blanc, Pinot Grigio, Champagne
- Chicken/pork: Chardonnay, Pinot Noir, Rosé
- Red meat: Cabernet Sauvignon, Malbec, Syrah
- Pasta with red sauce: Chianti, Sangiovese, Barbera
- When in doubt: Champagne goes with everything, and ordering it shows you know how to celebrate
These aren’t rigid rules—wine people will tell you there are exceptions to everything—but they’re reliable enough that you’ll never embarrass yourself.
Understand Price Context
This is crucial. At a nice restaurant in a major city, wines by the bottle typically range:
- $60-$100: Solid, respectable choices
- $100-$200: The sweet spot for most upscale dates
- $200-$400: Premium selections that show you appreciate quality
- $400+: Either he specifically said to go wild, or you’re celebrating something major
When I was at Scarpetta in Miami Beach with an SD who’d just closed a huge deal, I ordered a $250 Barolo because the occasion warranted it. But for a typical dinner at Quality Italian in NYC, I’d land in the $120-$180 range. Context matters.
According to research by anthropologist Dr. Helen Fisher, expert on romantic love and attraction, “Sharing novel experiences—including trying new foods and drinks—triggers dopamine release and increases emotional bonding between partners.” Translation: The actual wine matters less than the shared experience of choosing and enjoying it together.
Reading the Subtext: What This Moment Reveals About Your Arrangement
Okay, here’s where my years in the bowl really come into play. How he handles the wine moment—and your response to it—reveals a LOT about whether this arrangement has legs.
Green Flags:
He’s patient and encouraging when you’re figuring out your choice. Not hovering, not taking over, just giving you space to think. I had an SD who, when he saw me hesitating, casually started talking about the restaurant’s architecture to take pressure off—that’s emotional intelligence in action.
He builds on your choice regardless of what you pick. “Great choice” or “I’ve been wanting to try that region” shows he’s focused on the shared experience, not judging your wine knowledge. Quality men understand that making you comfortable serves everyone.
He uses it as a conversation starter about your tastes, experiences, travel. When I ordered a Spanish Albariño at Jaleo in DC, my SD launched into stories about his trip to Galicia, which led to planning a future trip together. That’s what you want—moments that deepen connection.
Red Flags:
He corrects your pronunciation in a condescending way or makes jokes at your expense. If he’s more focused on demonstrating his superiority than making you comfortable, that dynamic will permeate the entire arrangement. Trust me, I’ve seen it play out.
He looks annoyed or impatient when you take time to decide. This suggests he’s not actually interested in your input—he just wanted to look like he was. Men who get irritated during small moments of vulnerability will not support you during bigger challenges.
He immediately overrides your choice with “Actually, let me order” or contradicts you to the server. This is about control, not wine. If he can’t let you lead in this tiny way, consider what else he’ll need to dominate.
I’ll never forget a dinner at RPM Italian in Chicago where I ordered a Brunello, and the SD immediately told the server, “Actually, bring us the Amarone instead—she doesn’t know what she’s talking about.” I should’ve walked out right then. That arrangement lasted another miserable six weeks before I ended it, and every single issue traced back to his need to control everything.
Advanced Moves: Turning Wine into Your Secret Weapon
Once you’ve mastered the basics, you can start using wine moments strategically to strengthen your arrangement. This is next-level stuff that I’ve watched create incredible bonding experiences.
Suggest wine tastings as dates. A winery in Napa, a wine bar in the West Village, a tasting class at a local shop—these are intimate, conversational settings that let you both learn together. I did a vertical tasting (different vintages of the same wine) in Sonoma with an SD, and we still reference inside jokes from that afternoon three years later.
Remember his favorites and reference them. If he loved that Châteauneuf-du-Pape at Eleven Madison Park, bringing it up weeks later when you’re somewhere with a good French program shows you pay attention. Men in the bowl are so used to women who are checked out mentally—genuine interest stands out.
Gift thoughtfully. If you’re in a longer arrangement and want to give him something meaningful, a bottle from a region you discussed or a wine you discovered together hits different than generic gifts. I once gave an SD a 2015 Barolo (excellent vintage) from a producer we’d talked about wanting to try—he was genuinely touched because it showed I’d listened.
Use wine knowledge as a conversation bridge with his world. If he mentions a business trip to Bordeaux, asking about the wines there is a natural way to show interest in his life. These connections matter more than you’d think—they demonstrate you can operate comfortably in his environment.
What If You Genuinely Don’t Drink? (Handling the Unexpected)
Quick sidebar for my sugar babies who don’t drink alcohol for whatever reason—religious, health, personal preference, recovery. This actually gives you an opportunity to show confidence and set boundaries, which quality SDs respect.
Be straightforward: “I don’t drink, but I’d love to help you choose something you’d enjoy. What are you in the mood for?”
Most successful men appreciate directness. I’ve seen arrangements where the SB never drank, and it was never an issue because she communicated it confidently without making it a big deal.
Offer an alternative: “I’m not drinking tonight, but let’s get a bottle you’ll like—and I’ll steal a sip to taste it.”
This keeps the collaborative spirit while maintaining your boundary. You’re not refusing to engage; you’re just defining your terms of engagement.
And honestly? If a POT has a problem with you not drinking, that’s valuable information about his priorities and flexibility. The bowl has plenty of men who’ll respect your choices—don’t waste time on the ones who don’t.
The Real Lesson: It’s Always About Communication
Here’s what eight years of arrangements taught me that applies way beyond wine: the most successful sugar relationships happen when both people feel comfortable expressing preferences, admitting uncertainties, and collaborating on decisions—even small ones.
That moment when he asks you to choose the wine? It’s a microcosm of your entire dynamic. Are you comfortable taking initiative? Is he supportive when you do? Can you both handle it gracefully when things don’t go perfectly?
Dr. John Gottman, legendary relationships researcher, found that couples who navigate minor decisions well—showing respect, curiosity, and flexibility—have significantly higher relationship satisfaction. The same principle applies to sugar arrangements, maybe even more so given the unique challenges they present.
Every arrangement I’ve had that lasted more than a year included these little collaborative moments where we both showed up authentically. The ones that fizzled quickly? Usually because one of us—or both—was too busy performing instead of connecting.
Your Next Steps
So what do you actually do with all this? Here’s my challenge to you:
Before your next date: Spend 20 minutes exploring wine beyond just Googling “best wines.” Go to a wine shop, tell the person working there your budget and what foods you like, and ask for two recommendations. Buy a bottle, taste it at home, take notes. That small investment in yourself will pay dividends in confidence.
During the date: If the wine moment comes up, use one of the scripts I gave you—the one that feels most authentic to your personality. Pay attention not just to what you choose, but to how he responds. That response tells you whether this arrangement has the mutual respect foundation to thrive.
After the date: Reflect on how it felt. Did you enjoy taking the lead? Did he make you feel supported or judged? Are you starting to develop your own preferences? This self-awareness is what separates sugar babies who survive the bowl from those who truly thrive in it.
And look—if you completely freeze and hand the wine list back stammering, you’ll survive. I promise. We’ve all had awkward moments. The point isn’t to be perfect; it’s to keep showing up and learning from each experience.
The same confidence you’re building with texting, with negotiating allowances, with navigating the emotional complexities of arrangements—it all applies here. You’re developing a skillset that extends far beyond the bowl.
My Last Piece of Advice
Remember that night at Balthazar I mentioned at the beginning? When I froze over the wine list?
I ended up laughing, admitting I was intimidated by the selection, and asking the sommelier for help choosing something that would pair with our oysters and steak. My SD joined the conversation, we all landed on a gorgeous Châteauneuf-du-Pape, and it became a running joke between us for months. He’d text me photos of wine lists from wherever he was traveling, asking what I’d choose. That vulnerability and humor turned a potentially embarrassing moment into something that strengthened our connection.
So here’s the truth: the wine doesn’t actually matter. What matters is how you handle the moment—with confidence, authenticity, and a willingness to be human. Do that, and you’ll do just fine.
Now go order that wine, babe. You’ve got this. 🍷
