I once dated a “Mr. Big” in New York City, and let me tell you, if you’re looking for someone like him, you need to be prepared for some unexpected, sometimes bizarre, and often inconvenient experiences.

Dating a man with the aura and lifestyle of a character straight out of a Sex and the City episode may seem glamorous and enticing at first, but there’s a harsh reality that comes with it,

one that’s less about fairy-tale romance and more about navigating the unpredictable rollercoaster ride that is life with a wealthy, elusive, and slightly egotistical Manhattanite.

For starters, if you’re imagining a life full of romantic dinners, spontaneous trips to luxurious spots, and endless champagne toasts, you’re only seeing one side of the picture.

Sure, there are moments when everything feels like it’s straight out of a dream, but those moments are often short-lived, and they come with a price.

In this world, your dates might begin well enough with a helicopter ride or an impromptu getaway to the Hamptons, but they will inevitably end with you being unceremoniously dumped at your door at 4 a.m. As glamorous as these dates can be, they often come with a caveat: an unscheduled exit that feels more like a business transaction than a romantic goodbye.

There’s also the issue of time. Your Mr. Big is likely to have a schedule so packed that the concept of “spontaneity” only extends to late-night rendezvous after a long workday. You’ll quickly find that his life revolves around meetings, phone calls, and appointments that he must prioritize over anything resembling a casual, leisurely date. Whether it’s a late-night dinner that ends with him checking his phone every few minutes or an entire evening spent listening to him talk about his business ventures, it can be a lot to handle. The intimacy you crave is often overshadowed by his obsession with work, leaving you to feel like a secondary priority.

One of the more unexpected experiences of dating someone like this is the sheer amount of awkward, sometimes uncomfortable, moments that come with the territory. I remember one date where, over dinner, my Mr. Big casually mentioned his vasectomy like it was an anecdote he was proud of, bragging about how it was a “responsible decision” and how he had “taken care of things.” This sudden segue into his medical history might have been surprising to some, but to me, it was one of many examples of how disconnected he seemed from anything resembling normalcy when it came to relationships. Conversations that might typically explore emotions, past experiences, and future aspirations were often replaced by the minutiae of his lifestyle and an unrelenting focus on how his life worked on his terms.

What made it even more perplexing was how the whole dating dynamic felt transactional in a way. I couldn’t shake the sense that I was just another accessory in his life, a trophy of sorts to show off at parties or bring to his penthouse for late-night company. In the world of a Mr. Big, the lines between affection and convenience can blur, leaving you wondering if there’s any genuine connection beneath all the glitz and glam. His lavish gifts, expensive dinners, and glamorous outings were great at first, but they often felt more like an attempt to win me over with material wealth than any real emotional investment.

And then there’s the issue of exclusivity. In the world of Mr. Bigs, fidelity can sometimes be negotiable. I learned, rather quickly, that when you date someone who moves in the highest circles of New York’s elite, the expectations of commitment can become increasingly vague. They expect you to be patient, understanding, and forgiving when they cancel plans last minute or when they suddenly show up with someone else at a party. You begin to realize that the person you’re dating might have a whole other life that you’re not privy to, full of other women, business contacts, and people who fulfill different roles in his world. At times, it feels as though you’re just one piece of his well-curated, high-powered life, but not the one that comes first.

In the end, dating a Mr. Big might seem like a glamorous affair, but it can also be lonely, confusing, and exhausting. The excitement and thrill of the lifestyle can only take you so far before you start asking yourself whether you’re truly being seen for who you are, or if you’re just another player in his well-oiled, high-society machine. It’s a life full of superficial moments, fleeting affection, and an overwhelming amount of uncertainty, one that makes you question what you really want out of a relationship and whether the fantasy of it is truly worth the emotional toll it can take. If you’re still interested in dating a Mr. Big, just make sure you’re ready to handle the ups and downs—and that includes 4 a.m. exits and unexpected conversations about vasectomies.

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