What Is It Like To Date A Woman Way Out Of Your League?

Have you ever banged a woman you thought was impossibly hot, too hot for a mere peasant boy like yourself? Chances are, you haven’t. Most men don’t reach for the ass ring. Fear — and sometimes experience — cultivates an exquisite sense for one’s sexual rank, and an avoidance mentality that preempts rejection by sultry specimens thought to be “out of one’s league”.

But most men are not all men. A few warriors of the whiskered wound have banged out of their league, and lived to tell of the tail. Men with game will occasionally, maybe even often, bang women considered by the general population to be too beautiful for them. Other men will luck into an amazing fling with a superb hottie. Usually, some combination of fortuitous circumstance and seduction skill is the backdrop to a stunning mismatch between a regular guy and a boner fried bombshell.

In before the trick-less trolls and baffled haters hijack the substance of this post to nasalize their belief that men’s sexual value is judged by the same looks metric as women’s sexual value, let it be hammered into their blocklike skulls (again) that women judge a man’s mate worthiness by many measures, not least of which is his social value and his seductive savviness. So when we say that a man is shooting “out of his league”, we don’t necessarily mean the spectacle of a very ugly man with a beautiful woman (though it could mean that). We could also mean a man who compares favorably in the looks department with the woman he is dating, but who falls short in other equally important criteria. A good-looking but socially awkward nerd with a hottie is one such mismatch that strikes a discordant note on observers’ pattern-recognition tuning forks.

With that anti-hater disclaimer out of the way, we can move on to the meat and potatoes. Kai Peter Chang, a self-professed informal dating coach and boffer of beautiful babies, describes his experience dating what he figured (that’s the important qualifier) was a woman way out of his league.

Have you ever had the experience of getting a taste of a life light-years above your social class/station? 

Perhaps it’s being a guest at an extravagant $200,000 wedding thrown by a distant relative you barely know. All you can do is marvel at the gorgeous decor and decadent food you can never afford on your own.

Perhaps it’s a wealthy uncle/friend-of-a-friend who inexplicably allowed you take his $120,000 sports car for a spin around the neighborhood. All you can do is pray you don’t crash the car, or pop the clutch and embarrass yourself.

Perhaps you were summoned to an urgent work meeting that requires your presence thousands of miles away, and your employer authorized you to fly on the company jet (ordinarily reserved for its top executives). All you can do is fantasize about the day you’re powerful/rich enough to use a private jet for all your travel.

TL;DR: it’s like that – but involving the deepest part of sexuality and romance.

[A] number of years ago, I dated someone substantially “out of my league” for almost a year.

Her: a former Miss Hong Kong pageant gal, B-list actress/model/TVB television personality. In her prime, she was courted and pursued by the super-Alpha kings of Hong Kong: A-list movie stars, million-record-selling musicians, property tycoons, CEOs and power brokers at the apex of Hong Kong society.

Me: At the time, a Mergers & Acquisitions Analyst at an investment-banking firm – an easily-replacable cog in a financial behemoth, four years her junior. During that period, I commanded a low five-digit net worth, and no status to speak of. A nobody.

She told me afterward that she gave me her number because she was amused by the fact that I clearly didn’t recognize her; in Hong Kong, the only strangers who approach her are autograph-seekers and those who want to pose with her for a photo and I was utterly oblivious to her stature when I was flirting with her.

Nice neg.

It is also helpful to note that during this time, I was at still in first blush of youth – a few years out of college, filled with brazen and unrealistic cocky ambition of what I can accomplish, arrogant to the point of delusion, and impervious to feedback/advice.

I was also insecure as hell, and in complete denial about it.

With all that backdrop, the question was how did it feel as the “lesser” partner?

It was flattering, thrilling and unnerving all at once.

The more beautiful women you bed, the less unnerving (and thrilling, sadly) it becomes. You start to internalize the belief that you deserve them. This is the asshole’s secret of success.

Dating far above my station gave me a glimpse of the life that exists at a completely different strata of society. Growing up a son of broke-ass immigrant parents and attending public schools my entire life surrounded by others of modest immigrant socioeconomic background, the first thing that stood out was her nearly-unlimited access to favors and accouterments of her elevated station.

When you socialize with people who own spare yachts, faraway luxury properties and infrequently-used personal jets, you can cobble together an impromptu exotic vacation with a few phone calls. It will end up costing you little more than the price of a full tank of jet/yacht fuel and the promise of reciprocity of access to your own toys/properties at some unspecified future date.

I, of course, had nothing to offer in these types of trades – and that knowledge was a source of gnawing insecurity; while I was stupidly confident that I was just a few years/career moves away from joining the company of Hong Kong aristocracy on my own, my immediate financial circumstances were far more modest and I flew Coach to visit her, while she flew First Class or via private jet to rendezvous with me.

If you doubt your worth to a woman, she will feel compelled to agree with you. If you don’t doubt, neither will she.

The clandestine nature of our relationship (officially, she was the spoken-for consort of a powerful Hong Kong property tycoon two decades her senior and her lifestyle was bankrolled by his largesse) added a further element of illicit excitement; it was thrilling to be checking into hotels under fake names, arriving to locations at staggered times to avoid being seen together in public.

The sneaky fucker MO. It’s exciting because you know you’re getting something for free (outstanding pussy), that other men have to pay for in yachts and high society access.

In retrospect, I now understand what she meant when, right before the first time we slept together, she whispered in my ear “Please don’t fall in love with me.”

She was wiser and more pragmatic than I; she knew, better than I did at the time, the ephemeral nature of our doomed fling.

After several months of our relationship – which consisted writing letters to each other (she has a gorgeous, calligraphic handwriting and a wry playful prose that was a delight to read) and time-zone-spanning international phone calls, interspersed with week-long face-to-face rendezvous where we exhausted ourselves in hotel rooms in various locations along the Pacific rim, she tearfully confessed “Do you remember what I said to you that first night? I’m having a hard time following my own advice.”

It was as close as she could get to tell me she loved me, but it was clear that whatever we had would end someday.

Better to have loved a hottie and lost her, than to love a fug and keep her.

No doubt losing a pathway to high grade pussy is a blow to a man’s pleasure center, if not also his ego. But it was more dangerous for her to fall in love, because the nature of woman doesn’t allow for shared love between disparate men who offer her competing comforts beyond the wildest dreams of the average representative of her sex. She risked discovery, and the concomitant loss of feminine prestige and resources from her richer suitors. Truly beautiful women possess a degree of pragmatism that those who have little to lose can barely comprehend. Although if your charm is mesmerizing and your confidence imperturbable her love can bond her so tightly even the baubles of princes won’t steal her from your embrace.