ADVICE

The Secret to Dating a Woman Who’s Out of Your League

Miss Matchmaker AFA - Thailand
3 min readDec 6, 2023

Does her hair and her eyes simply take you away? Do you sit next to her and stare, slack-jawed with nothing to say?

According to American rock band Stephen Speaks, those signs point to you dating someone who is out of your league.

Silhouette of a man kissing the hand of a woman
Photo by 德綱 曾 on Unsplash

It’s a common phrase used to refer to someone who is either too pretty, too accomplished, or moving in social circles higher than yours.

In modern dating culture, where almost everyone is grouped into different kinds of tiers and compared to all sorts of people, you’ll likely meet a woman who everybody’s going to declare is just out of your league — that is if you haven’t already.

The question now is this: do you shoot your shot, or do you take a step back and accept that some women just aren’t meant to be yours?

Stop Following Invisible Rules

Here’s one of my favorite things to say to my clients and most of my friends every time they let another person’s opinion affect their love life:

“Who made them the boss of you?”

The same goes for you and any woman someone tells you is out of your league. According to whose standards? And why should you follow their judgment?

It’s especially telling if those kinds of comments come from a person who’s supposed to care about you. Some of them are not only insulting you and the qualities that make you desirable, but they’re also letting you know your dating options will always be limited. And that woman you like? Well, she simply isn’t one of them.

Sure, some of those people can mean well, but living your life based on other’s standards and following their invisible rules will only leave you anxious and insecure.

When it comes to dating and relationships, only the opinion of two people truly matters in the end: yours and that of the woman you like.

Do Not Put Her on a Pedestal

Another pitfall that plenty of men should avoid is putting the object of their desires and affection on a pedestal.

It’s one thing to consider a woman being out of your league, but it’s entirely another to think she’s perfect and beyond reproach. That’s usually a slippery slope that can lead you to have very unrealistic expectations.

No matter how beautiful or successful she is, that woman you like is still a flesh-and-blood human. She will have flaws and shortcomings. There will be days when she might even think you’re the one who is out of her league.

But the good news is if she’s looking for a loving and committed partner, she’ll want someone who will see her and love her for all that she is — imperfections included.

Dream Bigger and Aim Higher

Let’s say she really is out of your league. Now what?

Are you going to let that stop you from putting yourself out there, in hopes that she’ll see past all the ways she’s too good for the likes of you?

If social constructs that dictate who can date whom truly matter to you, you can use them as inspiration instead of a barrier. You may not be able to easily address things like physical looks or age or the circumstances of your birth, but there are still things you can do to make yourself deserving of someone you love.

She’s wealthier and more successful than you are? Work harder.

She’s more fit or conventionally attractive? Start taking care of yourself.

She’s smarter and knows a lot about the world? Read and grab more opportunities to improve yourself.

So what if the woman you want to date starts off as out of your league? There are plenty of ways for you to catch up and close the gap.

It’s all going to be worth it for a woman who is all that you need and all that you see, don’t you think?

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