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The dos and don’ts of dating “out of your league”

Sometimes, dating "out of your league" can actually work. Just ask Meghan Markle, who is dating Prince Harry.
Sometimes, dating “out of your league” can actually work. Just ask Meghan Markle, who is dating Prince Harry.

How many times have you spotted someone you’d like to date, only to have that little voice inside your head tell you she’s/he’s “out of your league”? Should you ignore that voice – or listen to it? The answer depends on a variety of circumstances. 

As elite matchmakers, we only accept clients who we believe we can match. As we always say, we stress quality over quantity. Yet even catches can have unrealistic expectations. 

Much of this is cultural. Society tells us that “marrying up” – or deliberately searching for someone wealthier, more successful, or better looking than we are — is the way to go. Who among us didn’t cheer for Cinderella when the Prince placed that glass slipper on her foot? Or commiserate with Snow White when she sang that someday, her prince would come? 

Unfortunately, there’s an enormous difference between fairy tales and the real world. When it comes to dating, I always encourage clients to be hopeful and realistic. A man with model-like looks probably isn’t going to be interested in you unless you also look like a model. A wealthy, successful woman probably isn’t going to put you on her radar unless you come close to where she is in life.

But then again, the key word here is “probably.” Because there are those rare – and I do mean RARE – cases where going out of your league proves successful.

A few weeks ago, we wrote about Prince Harry and his romance with actress Meghan Markle. Some would say that Meghan is out of Harry’s league. She is certainly beautiful, but she’s not royalty. And she’s a working actress, but she doesn’t exactly have Meryl Streep’s name recognition. (Not yet, anyway.) 

The key here is that Harry and Meghan both have attitudes and beliefs that could very well transcend the usual norms of wealth, class, and success, and ultimately lead to a trip down the aisle. Harry has the ability to be very open-minded about the type of woman he dates. And even before she met Harry, Meghan possessed a keen sense of who she is. She quite rightly believes that Harry is as lucky to have her as she is to have him.

Too often, it’s a deep-rooted lack of self-esteem that makes people yearn for dating someone out of their league. They don’t like who they are, or where they are, and they’re hoping for someone to “rescue” them. The trouble is, there are very few people who want to do that. Even if they are willing, that’s not necessarily a good thing, because these types often demand someone that they can over-power. This is not anyone’s idea of an equal relationship. 

So, while I don’t normally recommend dating out of your league, I would say it’s okay if – and only if – you know yourself well enough to overcome any obstacles. 

It’s sort of like playing the lottery. There are people in this world who know full well that their chances of winning are slim, yet they still throw in a few bucks just because they know that there’s a chance (albeit a slim one) that they’ll hit the jackpot. When they don’t, they shrug it off, maybe joke a little (“Well, I guess they will see me in the office Monday morning after all.”) and let life go on as normal. This is exactly the type of person you must be to date out of your league.

If you’re really hoping to find lasting love, there’s something to be said for dating within your league. It shows that you know yourself well, and have realistic expectations. After all, love has nothing to do with wealth, looks, or even success. It’s about two people who support one another, understand one another, and stick with each other through thick and thin. It’s about being with someone who feels like a comfortable pair of shoes, someone you can trust and be your true self. This holds true, no matter what league you’re in.


Dr. Nancy



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