Learning How to Date Out of Your League

Man in TuxedoEach of us, at one time or another, aspires to greatness, or at least great wealth, power, and prestige. Admittedly, fame and fortune for the vast majority of humans on the planet is a non issue. Most of us will have more or less typical lives, living out our average existences without gaining much attention or distinguishing ourselves from countless others in the same boat.

This is just as true when it comes to relationships. As the old saying goes, water seeks its own level. This means that most of us will scout for significant others in the same banal zone of mediocrity into which we ourselves fall. In this case, like attracts like and, while there is some research to support the notion that opposite personality types are often found to attract, people who are polar opposites on the social scale will generally repel one another.

Money Talks and Bullshit Walks

The easiest lesson to learn is that you can date anyone you want if you have enough money. Money trumps age, good looks, intelligence, and several other factors. A man or a woman with the funds can essentially buy good company or, at the very least, attractive young playthings, trophies if you will, to hang on their arm or toss into bed.

You don’t even need a lot of money. You certainly don’t have to be Donald Trump to exercise this principle. Often, flash money is all that’s necessary; a thick wad of bills in your pocket and the willingness to spend it while showing your person of interest a good time. We used to do this ourselves once in a while, standing in line at the local bank with commission checks of $4,000 or $5,000.

We’d position ourselves in line with an attractive female, usually much younger and prettier than we were used to, and start talking to ourselves. “One week’s pay, oh what am I going to do with all of this?” Once the girl started talking, we never failed to get a phone number right then and there. In California, anything goes. On paydays, we’d have the same kind of luck everywhere, from upscale bars to the produce aisles in supermarkets. Most women, in our experience, have trouble saying “no” to a pocketful of loot.

Dress the Part

The first thing that Richard Gere did in Pretty Woman was to take Julia Roberts shopping. The clothes make the man and the accessories make the woman. They can spot you a mile away wearing cheap, ill-fitting clothes. If you’re looking to go upscale with your dating choices then you have to look and act the part. Lessons on manners come later, but the first and best impression you’ll make is by dressing well.

Again, you don’t have to indulge yourself in thousand-dollar custom suits and outfits to succeed in the major leagues. You just don’t want to look like a hooker or like you only own one outfit and you’ve been sleeping in it for a week. Whether you are big or small, short or tall, fit is very important. We all have at least one friend or family member who has an eye for what will look good on you and where to find it.

We come from a long line of world-class shoppers. Designer duds can be had for a fraction of their original cost on the clearance rack. You should also avoid buying clothes in season. By July, all of the spring and summer ware will be marked down. You’ll find the same kinds of bargains for winter clothes in January. Just make sure you find the appropriate size and/or spend the few extra dollars to have a professional seamstress or tailor alter the garment to suit you.

Put Yourself in Their World

In the major leagues, players demand and receive more respect. It is the same in any stratum of society. The bigger the player, the more powerful, the more prestigious, the more respect he or she will command. To succeed in their world, you need to become a part of it―eat where they eat, drink where they drink, and go where they go.

Learn to be comfortable in upscale establishments, places with maître d’s and valet parking. You don’t have to become a member to understand the rituals and traditions of the local country and garden club set. Learn what the members of that particular group your intended date belongs to are talking about and where their political leanings are.

Find out what they do in their free time and where they spend their vacations. You don’t have to be well-heeled or well-traveled to express interest and hold your own in conversations about any of these things. All you need is a computer or a handy smart phone and you too can be well-versed on what the intelligentsia is buzzing about over cocktails at the club.

Go Big or Go Home

Once you find the right clothes, accoutrements, and atmosphere for your league-hopping dates, enjoy yourself; you may never get a better opportunity. You should also remember that he or she may be looking to date someone out of their league as well.