Here’s what nobody tells you about meeting wealthy men: they’re not just hanging out at random five-star hotels hoping to bump into sugar babies. They’re living their actual lives—pursuing hobbies, building networks, doing the things that made them successful in the first place. And if you want to connect with them authentically (which, trust me, is the only way this works long-term), you need to show up where their real interests take them.
I remember my second year in the bowl, I was so focused on “being seen” at the right restaurants that I completely missed the point. I’d dress up, sit at hotel bars in Miami, and wonder why I kept attracting the wrong type. Then I met James—a tech investor who I ran into at an art gallery opening in Wynwood. We spent two hours debating a Basquiat piece, and that conversation led to a two-year arrangement that genuinely changed my life. Not because of the allowance (though that was generous), but because we connected over something real first.
So yeah, I’m gonna walk you through 15 places where wealthy, generous men actually spend their time. But more importantly, I’ll tell you how to approach these spaces authentically—because showing up isn’t enough. You need to belong there, or at least look like you do.
1. High-End Gyms and Wellness Clubs (Equinox, Lifetime Athletic, Private Training Studios)
Okay, this one’s tactical as hell, and I love it. Wealthy men are obsessive about their health—it’s how they maintain the energy to run their empires. I’m talking about places like Equinox in Hudson Yards (NYC) or the private training clubs in West Hollywood.
Here’s what I learned: don’t just get a membership and show up in full makeup at 6 AM looking lost on the StairMaster. That screams “I’m here to meet men,” and high-quality guys can smell that from across the weight room. Instead, actually use the gym. Take the boutique classes—Barry’s Bootcamp, SoulCycle, the golf simulator sessions. Show up consistently at the same times. Let familiarity build naturally.
I met David, a hedge fund manager, at an Equinox in Tribeca. We kept ending up at the same 7 AM spin class for weeks before he finally asked if I wanted to grab a smoothie after. That casual conversation turned into coffee, then dinner, then—well, you get it. The key was that I wasn’t performing for him; I was genuinely there for my workout, and that authenticity made all the difference.
Pro tip: If you’re serious about this approach, invest in good workout gear. Lululemon, Alo Yoga, Outdoor Voices—these signal you take wellness seriously. And please, for the love of God, don’t interrupt someone mid-set. Wait for natural moments—the juice bar, the lobby, after class.
2. Golf Courses and Country Clubs
Listen, I get it—golf isn’t everyone’s thing. But if you can learn to play (or at least appreciate it), you’re opening doors to one of the most exclusive networking spaces wealthy men occupy. I’m talking about places like Winged Foot in Westchester, Pebble Beach in California, or Trump National in Bedminster.
The thing about golf is it’s four hours of uninterrupted conversation. No phones (mostly), no distractions—just you, him, and the game. That’s intimacy-building gold. But here’s where most women mess this up: they try to fake interest. Don’t. If you’re gonna do this, actually learn the game. Take lessons at a public course first, get comfortable with the basics, then join a country club or attend charity tournaments.
I didn’t grow up playing golf, but when I moved to San Francisco, I took lessons at Presidio Golf Course for three months before joining a friend at Olympic Club for a member-guest event. That’s where I met Richard, a real estate developer who appreciated that I wasn’t just there to look cute in a golf skirt (though, yeah, that didn’t hurt either). We played nine holes, talked about his commercial projects and my interest in property investment, and by the 18th hole, he’d asked if I wanted to discuss “business opportunities” over dinner.
What actually works: Attend charity golf tournaments, take lessons at upscale courses, or join women’s golf leagues at country clubs. Even if you don’t play, many clubs have social memberships that give you access to dining and events—which can lead to first date opportunities with members you meet casually.
3. Yacht Clubs and Marina Events
There’s something about men with boats, I swear. Maybe it’s the freedom, the status symbol, or just the fact that maintaining a yacht means serious disposable income—whatever it is, yacht clubs are goldmines.
I spent a summer in Miami, and let me tell you, the scene at Miami Beach Marina and Coconut Grove Sailing Club was insane. Here’s the move: many yacht clubs host weekly social sails, regattas, and dockside cocktail parties that are open to guests if you know a member—or if you’re willing to take sailing lessons there.
I met Marco (Italian expat, luxury car importer) at a sunset sail event at Coral Reef Yacht Club. I’d signed up for a women’s sailing course earlier that month, which gave me legitimate access to club events. We started chatting about his Azimut yacht, I shared that I was learning to sail, and he offered to take me out the following weekend. That three-hour sail turned into a six-month arrangement that included trips to the Bahamas and Turks and Caicos.
The reality check: You can’t just wander into a yacht club off the street. These places are exclusive for a reason. But you can take sailing lessons, attend public regattas, or befriend someone with access. Once you’re in, be genuine about your interest—ask about the boats, the sailing culture, the lifestyle. Men love sharing their passions, especially if you’re actually listening.
4. Charity Galas and Fundraising Events
Okay, real talk—this is where I’ve had some of my most successful meets. Wealthy men show up to these events to network, be seen, and yes, feel good about giving back. And they’re usually in an open, social mindset, which makes approaching them way easier than, say, at a business conference where they’re in work mode.
Places like the Costume Institute Gala in NYC, Art Basel charity auctions in Miami, or local children’s hospital fundraisers in any major city—these are where successful, generous men congregate. And here’s the beautiful part: you already have a conversation starter built in. You’re both there supporting a cause.
I attended a gala for a cancer research foundation in Chicago (through a friend who bought a table). I wore a floor-length emerald gown, bid on a few silent auction items to show I was there for the cause, and ended up sitting next to Thomas, a pharmaceutical executive. We talked about the foundation’s work, his late mother (who’d battled cancer), and by dessert, he’d asked if I’d like to continue the conversation over drinks the next evening. That arrangement lasted over a year and taught me so much about providing the girlfriend experience in a way that felt natural and unforced.
How to access these events: Check sites like Eventbrite or local society pages for charity galas. Tickets can be pricey ($250–$1,000+), but think of it as an investment. Alternatively, volunteer for the organizing committee—many events need help, and that gets you in the door for free while building connections. Just make sure you actually care about the cause, because performative charity is transparent and off-putting.
5. Art Galleries, Auctions, and Museum Openings
There’s a certain type of wealthy man who’s drawn to the art world—collectors, investors, patrons. And honestly, these guys tend to be more intellectually curious and open-minded, which often translates to better arrangement dynamics.
I used to hit up gallery openings in Chelsea (NYC) almost every Thursday. Places like Gagosian, David Zwirner, and Pace Gallery host free public openings with wine and networking. You don’t need to be an art expert, but you should have some basic knowledge and genuine curiosity. I spent months reading Artsy articles and visiting museums before I felt comfortable discussing contemporary art.
That preparation paid off when I met Alexander, a venture capitalist with a serious art collection, at a Basquiat exhibit opening at the Broad in LA. We debated whether Basquiat’s later work was stronger than his early pieces—I held my own in that conversation, and he was impressed. We exchanged numbers, met for coffee at Republique the next week, and within a month, we had an arrangement that included him mentoring me on art investment (and yes, eventually buying me a small piece for my own collection).
Pro tip: Follow gallery Instagram accounts, sign up for mailing lists, and don’t be afraid to ask questions during openings. Men love playing the expert, and asking thoughtful questions is a great way to spark conversation. Just avoid the “I don’t really get modern art” angle—it reads as intellectually lazy.
6. Wine Tastings and Exclusive Wine Clubs
Wine culture is huge among affluent men, especially those in their 40s and up. I’m talking about places like The Wine House in LA, Sherry-Lehmann in NYC, or private tastings at Napa wineries like Opus One or Harlan Estate.
The beauty of wine tastings is they’re inherently social and sensory—you’re supposed to talk, share impressions, and explore together. It’s intimate without being overtly romantic, which is perfect for initial connections.
I attended a private tasting at a wine collector’s home in San Francisco (got the invite through a friend-of-a-friend situation). There were maybe 15 people there, and I ended up in a conversation with Gregory, a tech executive, about a 2005 Bordeaux we were sampling. He appreciated that I’d done my homework—I knew the region, the vintage, and could articulate what I was tasting. That led to him inviting me to a dinner at Gary Danko the following week, which evolved into a mutually beneficial arrangement.
How to break in: Start with public tastings at upscale wine shops, then join wine clubs or attend winery events if you’re near Napa, Sonoma, or other wine regions. Take a sommelier course if you’re serious—it’s a worthwhile investment that signals sophistication and commitment to learning.
7. Luxury and Classic Car Shows
Men and their cars—it’s a thing, and if you can tap into that passion, you’ve got a serious advantage. Events like Monterey Car Week, the Pebble Beach Concours d’Elegance, or even local supercar meetups attract wealthy enthusiasts.
Here’s what I learned: you don’t need to be a gearhead, but you should show genuine curiosity. I went to a Lamborghini rally in Miami Beach a few years back (my friend’s ex was participating), and I made it a point to ask specific questions about the cars—engineering, design, performance. That authenticity stood out.
I met Vincent, a real estate mogul with a collection of vintage Ferraris, at that event. He was showing off his 1967 Ferrari 275 GTB, and I asked about the restoration process instead of just saying “nice car.” That question led to a 20-minute conversation, which led to dinner at Zuma that night, which—you see the pattern here.
The move: Attend public car shows, follow supercar clubs on social media, and if you’re really committed, take an exotic car driving experience course. It shows you’re not just there to look pretty—you’re actually interested in the culture.
8. Private Members Clubs (Soho House, Core Club, Casa Cipriani)
These exclusive clubs are where the elite go to unwind, network, and—let’s be honest—escape people like us who are trying to meet them. But if you can get access (and that’s a big if), they’re incredibly effective for making connections.
I’m a member at Soho House in West Hollywood, and I can’t overstate how valuable it’s been. The vibe is relaxed, everyone’s successful but not showy about it, and there’s an unspoken understanding that you’re there to connect. I’ve met multiple potential arrangements just by being a regular at the rooftop pool or attending their member events.
The key is not treating it like a hunting ground. These spaces are sacred to members—it’s where they go to not be hustled. So you show up, you’re friendly, you engage in natural conversation, and you let things unfold organically. I met Brandon, a film producer, at a Soho House screening event. We started chatting about the film afterward, discovered we both loved indie cinema, and ended up dating (and yes, it turned into an arrangement) for over a year.
Getting in: Memberships are expensive ($2,000–$4,000/year) and often require an application process with referrals. If you can’t swing that, attend public events these clubs occasionally host, or befriend a member who can bring you as a guest. Just remember—if you abuse the privilege, you’ll get blacklisted fast.
9. Upscale Hotel Bars and Rooftop Lounges
Okay, this is the most obvious one on the list, but there’s a right way and a wrong way to do it. Yes, hotel bars at places like The Polo Bar at The Beverly Hills Hotel, The NoMad Bar in NYC, or The Setai in Miami attract wealthy travelers and locals. But if you’re just camped out at the bar every night looking like you’re working, you’re gonna attract the wrong attention.
The right approach: go with a friend, have an actual plan (dinner reservation, meeting someone), and let encounters happen naturally. I’ve had success at places like Employees Only in NYC and Catch LA—not because I was obviously available, but because I was there enjoying myself, and that confidence attracted quality men.
I met Julian, a hedge fund manager, at The Roof at Park South in NYC. I was there with a girlfriend celebrating her promotion, and he sent over a bottle of champagne with a note. We ended up chatting for an hour after my friend left, and that casual conversation led to a dinner date and eventually a very generous arrangement.
Avoid this mistake: Don’t sit alone at a bar on your phone looking bored. Don’t dress like you’re going to a nightclub (hotel bars are sophisticated, not sexy). And for God’s sake, don’t accept drinks from every man who offers—it sets the wrong tone. Be selective to avoid fake sugar daddies who just want free company.
10. Business Conferences and Industry Events
This is an underrated strategy. Conferences like TechCrunch Disrupt, Milken Institute Global Conference, or even local chamber of commerce events are packed with successful, ambitious men who are in networking mode—which means they’re open to meeting new people.
The trick is you need a legitimate reason to be there. I’ve attended conferences as a “consultant” (which, honestly, I kind of am now), and I’ve volunteered at registration desks to get free access. Once you’re in, work the room—attend panels, ask thoughtful questions, and network during breaks.
I met Stephen, a biotech entrepreneur, at a healthcare innovation summit in San Diego. I was genuinely interested in the topic (I’d been researching health tech investments), and we ended up in a debate about FDA regulations during a coffee break. That conversation impressed him enough that he invited me to dinner to continue the discussion, and we built a connection from there.
The strategy: Choose conferences in industries you’re actually interested in (tech, finance, real estate, healthcare). Do your research beforehand so you can contribute to conversations. And dress the part—business professional, not cocktail attire. You want to be taken seriously first, attractive second.
11. Ski Resorts and Mountain Retreats (Aspen, Vail, Park City)
If you can swing a winter trip to a luxury ski destination, do it. Places like Aspen, Vail, and Park City are playgrounds for the wealthy during ski season, and the apres-ski scene is perfect for meeting men in a relaxed, fun environment.
I spent a week in Aspen a few winters ago (stayed with a friend who had a condo), and the amount of wealth concentrated in that small town was staggering. We hit up spots like Cloud Nine Alpine Bistro for lunch on the mountain and Caribou Club for evening drinks—both packed with successful men unwinding after a day on the slopes.
The vibe in ski towns is different—everyone’s more open, more adventurous. I met Christopher, a private equity guy from Chicago, at the base of Aspen Mountain. We were both waiting for the gondola, started chatting about the conditions, and ended up skiing together for the afternoon. That turned into dinner at Matsuhisa, which turned into a winter arrangement that included trips to his place in Vail.
Pro tip: If you can’t afford the trip, consider working at a resort for a season—you’ll get access to the social scene and might meet someone. Or, if you have friends with places in ski towns, visit during peak season and make the most of it.
12. Theater, Opera, and Symphony Performances
The cultural arts scene attracts a specific type of wealthy man—educated, refined, often looking for intellectual companionship. Places like Lincoln Center in NYC, the Lyric Opera in Chicago, or the LA Philharmonic at Walt Disney Concert Hall are prime spots.
Here’s the thing: you can’t fake a love for opera or theater. Well, you can, but it’ll show. So if this isn’t your world, maybe skip it. But if you genuinely enjoy these performances, they’re incredible for meeting quality men.
I attended a production of La Bohème at the Metropolitan Opera (splurged on a good seat in the orchestra section), and during intermission, I struck up a conversation with Edward, a corporate attorney, about the soprano’s performance. We ended up getting drinks after the show at The Smith, and that led to a months-long arrangement where he’d take me to performances and dinners—with a generous monthly allowance that made it more than worth my time.
The approach: Buy single tickets to performances (subscriptions are expensive), dress elegantly, and use intermissions to socialize. Ask about someone’s impressions of the performance, discuss the production—let your genuine interest guide the conversation.
13. Polo Matches and Equestrian Events
Polo is the sport of kings, and the social scene around it is as exclusive as it gets. Events like the Bridgehampton Polo Club matches or the Palm Beach Polo season attract serious wealth.
I went to a polo match in the Hamptons with a friend who had connections (sensing a theme here?), and the whole scene was like stepping into another world—tailgates with champagne, designer sundresses, men in linen suits. It’s less about the sport and more about the lifestyle, which makes it perfect for sugar dating.
I met Philippe, a French investor, at a tailgate party between matches. We talked about his love for horses (he owned a few polo ponies), and I shared that I’d taken riding lessons as a kid. That common ground was enough to spark a connection, and he invited me to dinner at The American Hotel in Sag Harbor that evening.
Breaking in: Attend public matches, volunteer with equestrian charities, or take riding lessons at stables that cater to the wealthy. Even if you’re not riding polo ponies, being around that world gets you access.
14. High-Stakes Poker Games and Exclusive Casinos
If you can handle the intensity, high-stakes poker rooms and exclusive casinos (think Bellagio in Vegas, The Wynn, or private games in major cities) attract risk-takers with money to burn.
I’m not much of a gambler, but I learned basic poker and sat in on a few mid-stakes games in Vegas. The energy is electric, and men at these tables are often in a social, competitive mood. I met Daniel, a tech entrepreneur, at a table at Aria. I wasn’t playing—I was watching and occasionally commenting on hands, which he found refreshing. We ended up talking during a break, and he invited me to join him for dinner at Carbone in the Cosmopolitan.
Important: Don’t try to play if you don’t know what you’re doing—you’ll lose money and look foolish. Instead, observe, be social, and let your presence attract attention. And obviously, be smart about safety—stick to reputable casinos, not sketchy underground games.
15. Luxury Resorts and Exclusive Travel Destinations
This is the long game, but it works. Places like Amangiri in Utah, Aman resorts worldwide, or private island retreats like Necker Island attract ultra-wealthy travelers looking to unwind—and often, they’re open to meeting interesting people.
I saved up and treated myself to a solo trip to Amanpuri in Phuket (okay, I also had some help from a previous arrangement), and the caliber of people I met there was unreal. At the resort’s beach club, I started chatting with Michael, a real estate developer from Hong Kong, about the property’s design. That conversation turned into snorkeling together the next day, then dinners throughout the rest of the trip, and eventually a long-distance arrangement that included meeting up in various cities.
The reality: These trips are expensive, so you need to be strategic. Look for shoulder season deals, use points if you travel hack, or consider working at luxury resorts to get insider access. Once you’re there, be present and approachable—wealthy men on vacation are often more relaxed and open to connection.
What Nobody Tells You About All of This
Here’s the truth that cuts through all the strategy: showing up at these places is only 10% of the equation. The other 90% is how you show up.
As relationship researcher Esther Perel notes in her work on modern relationships, “The quality of our relationships determines the quality of our lives.” In sugar dating, that quality starts with authenticity. You can go to every yacht club and charity gala in the world, but if you’re performing, if you’re pretending to be someone you’re not, high-caliber men will see through it instantly.
Successful men have been approached by beautiful women their entire adult lives. They can spot insincerity from a mile away. What they can’t resist is a woman who’s genuinely interested in their world, who brings her own passions and intelligence to the table, and who isn’t afraid to be real.
I’ve made the mistake of trying to be what I thought a man wanted—more demure, more agreeable, more everything. It never worked. The arrangements that thrived were the ones where I showed up as myself, stated my boundaries clearly, and connected over real, shared interests. That’s when the real benefits started flowing—not just financially, but emotionally and intellectually too.
So yeah, go to these places. Invest in the memberships, take the lessons, attend the events. But do it because you’re genuinely curious about that world, because you want to expand your own horizons. The right men will notice that authenticity, and when they do, the connection you build will be so much deeper than anything you could’ve forced.
And look—I know this lifestyle isn’t for everyone. It takes confidence, adaptability, and a willingness to put yourself out there in spaces that might initially feel uncomfortable. But if you’re serious about meeting generous, successful men who can genuinely enhance your life (and vice versa), these are the places where real connections happen.
Just remember: you’re not hunting. You’re connecting. There’s a huge difference, and the men worth your time can absolutely tell which one you’re doing.
