I keep seeing these animated relationship videos on Facebook, and I have to admit, I find them entertaining.
There is this man, Richard. Richard is handsome, successful, financially comfortable, and seems perfectly capable of planning a beautiful date. He takes these gorgeous women on amazing trips, gives them lovely experiences, treats them well, and somehow the woman is still unhappy.
Something is wrong with the hotel. The vacation is not impressive enough. She wants more. She complains. She does not seem particularly grateful.
And every time I watch one of these stories, I get the feeling I am supposed to come away thinking:
Women are impossible to please.
Except I keep thinking something completely different.
Richard, darling. I think you keep picking the wrong women.
At some point, if the same thing keeps happening with different people, I think we have to stop looking only at the people we dated and start looking at the people we keep choosing.
Because Richard seems to be doing plenty once he gets into the relationship.
I am more curious about what he is doing before he gets there.
Having Options Is Not the Same as Choosing Well
Successful, attractive people usually have options.
That is simply reality.
If you are good-looking, financially secure, interesting, confident, successful, or some combination of those things, more people are probably going to be interested in you.
But I think there is a mistake people sometimes make when they have a lot of choices.
They assume having more options means they have better options.
It does not.
Having twenty attractive people interested in you does not mean any of those twenty people are compatible with you. A hundred matches on a dating app do not equal one healthy relationship.
I know this firsthand from dating apps. I have had hundreds of likes. On paper, that sounds like having endless options.
But likes are not relationships.
Matches are not compatibility.
And having a large number of people interested in you does not mean you are going to want any of them back.
I have opened an app with plenty of attention waiting for me and still walked away without choosing anyone.
That is the part people sometimes miss when they talk about having options. A large dating pool may tell you that you are desirable. It does not tell you that the right person for you is standing somewhere inside it.
Sometimes more choices simply mean more people to sort through.
Options only tell you that people are interested.
They do not tell you why they are interested, and they certainly do not tell you whether the two of you are capable of building a life together.
That is where I think desirability and compatibility get confused.
You can be highly desirable and still repeatedly choose people who are completely wrong for you.
Actually, having more options might make that easier.
What Are They Choosing You For?
This is where I think successful people, especially successful men, sometimes need to become a little more curious.
If part of what makes you attractive is your success, your lifestyle, your home, your travel, your money, or the experiences you can provide, some women are naturally going to be attracted to those things.
And I want to be careful here because wanting financial stability or a comfortable life does not automatically make a woman shallow.
I want stability too.
Most people do.
Success is attractive. Ambition can be attractive. Financial responsibility is attractive.
The question is whether there is enough between two people when you take the success away.
Does she enjoy talking to you when you are not taking her somewhere?
Does she like your mind?
Your humor?
Your personality?
Does she care about the ordinary details of your life?
And the same question works in reverse.
If a man is mainly choosing a woman because she is beautiful, young, sexy, stylish, or looks impressive beside him, then perhaps he should not be shocked later when he realizes he never spent much time learning who she actually was.
If he is choosing her mostly for what she looks like, while she is choosing him mostly for what his life looks like, maybe neither one of them has done anything dishonest.
Maybe they simply chose each other for qualities that had very little to do with whether they could actually be happy together.
Then six months later, he thinks she is ungrateful.
She thinks he is not enough.
Meanwhile, I am sitting there watching another beautiful animated vacation thinking, I think we missed something during casting.
The Woman You Really Want May Be Picky Too
There is another part of this that I find interesting.
Successful people sometimes forget that the people they really want may have options too.
There are beautiful women who are also successful.
Women with careers, money, homes, friends, families, interests, and full lives of their own.
There are women who can take themselves to dinner.
Women who can buy their own handbag.
Women who have already traveled.
Women who are not particularly dazzled because a man booked a nice hotel.
And those women may be just as selective as the successful man who says he has plenty of options.
That changes the dynamic.
Now success alone is not enough.
Now you actually have to connect.
You have to be interesting beyond your résumé.
You have to listen.
You have to have emotional depth.
You have to make her laugh.
You need shared values.
There has to be chemistry.
And she may be looking at you just as carefully as you are looking at her.
The women who are most immediately impressed by what a successful man has may also be the easiest for him to attract.
That does not make those women bad.
But the woman who already has a full life may require something different.
Not more money.
More you.
And perhaps that takes longer to discover.
What Are You Actually Choosing For?
I think this is the question underneath all of it.
What are you actually choosing for?
There is nothing wrong with wanting someone beautiful.
There is nothing wrong with wanting someone successful, ambitious, fit, funny, younger, older, feminine, masculine, adventurous, established, educated, or whatever else genuinely attracts you.
I have preferences too.
We all do.
Physical attraction matters.
Lifestyle matters.
But I think we have to ask whether the qualities getting someone through the front door have anything to do with the things we eventually complain are missing.
If most of your requirements are about appearance and lifestyle, but every relationship ends because you want more depth, gratitude, loyalty, consistency, or emotional maturity, perhaps those qualities need to move higher on the list.
And women do this too.
We can keep choosing the same charming, exciting, emotionally unavailable man in a different body and eventually ask:
Why are men like this?
At some point, we have to ask ourselves the same question I would ask Richard:
What keeps attracting me to this particular type?
Sometimes our “type” is simply the pattern we have not questioned yet.
Maybe we choose chemistry when what we really need is consistency.
Maybe we choose excitement when what we keep asking for later is peace.
Maybe we choose someone mysterious and then spend six months wishing he would communicate.
Maybe we choose the beautiful woman who loves the lifestyle and later wonder why the lifestyle matters so much to her.
We cannot always separate ourselves from the patterns we keep repeating.
Being Picky Is Not the Problem
I actually think people should be picky about relationships.
Very picky.
This is someone who may eventually share your home, your finances, your body, your family, your problems, your mornings, your future.
Please do not choose that casually.
But being selective and looking for perfection are not the same thing.
There is probably no human being who will walk into your life checking every single box you wrote down before meeting them.
And sometimes the boxes themselves are the problem.
Maybe the woman who would make you incredibly happy is a little outside the age range you imagined.
Maybe she is busier because she has built a life and career of her own.
Maybe she is not immediately impressed by you.
Maybe she challenges you.
Maybe she says no sometimes.
Maybe she does not need you financially, which means you have to find out whether she actually likes you.
That might be uncomfortable.
It also might be exactly what you need.
And women can do the same thing with men.
Maybe the man who would make you feel secure is not the one who gives you butterflies within five minutes.
Maybe he is not mysterious at all.
Maybe he actually texts back.
Terrifying, I know.
Sometimes we become so attached to what attraction is supposed to feel like that we keep choosing the same feeling instead of looking at where that feeling actually leads us.
Repetition Is Information
This is probably the biggest thing I would say to Richard.
If the same problem keeps appearing in different relationships, pay attention to the repetition.
If every woman you date eventually seems more interested in what you provide than in who you are, perhaps you are leading too heavily with what you provide.
If every girlfriend is beautiful but you later complain that you cannot connect with her emotionally, maybe beauty is doing too much of the screening.
If every person you date becomes demanding, unavailable, jealous, chaotic, distant, or whatever the repeating issue happens to be, eventually the question has to become bigger than:
Why do people keep doing this to me?
It becomes:
Why does this particular person keep feeling attractive to me in the beginning?
That is a harder question.
But probably a more useful one.
Because there is information in repetition.
You Cannot Love Someone Into Compatibility
This is also where I think generosity gets misunderstood.
You cannot make someone compatible with you by treating them better.
You cannot take someone whose values are completely different from yours and love them into becoming the person you hoped they would be.
You cannot create gratitude with a luxury vacation.
You cannot create character with gifts.
You cannot create emotional maturity by being patient enough.
You can certainly inspire someone.
People grow inside good relationships.
But there has to be something compatible there to begin with.
Otherwise, you are just pouring more into a relationship that was never built for what you want from it.
That does not make either person bad.
Sometimes two perfectly decent people simply want different things.
Sometimes the woman who loves luxury is not shallow. Maybe that lifestyle is genuinely important to her.
And maybe the man who wants simplicity is not cheap.
They may just want very different lives.
That is incompatibility.
No villain required.
The Wrong Person May Be Easier to Attract
I also think there is something else successful people sometimes overlook.
The person who gives you a chance most quickly is not necessarily the person best suited to you.
Sometimes attraction is immediate because the things you offer line up perfectly with what the other person is looking for.
Sometimes that is wonderful.
Sometimes it is not.
The woman who is impressed by your lifestyle may respond very quickly to that lifestyle.
Meanwhile, the woman who already has her own life may be watching longer.
She wants to know what you are like.
How you treat people.
What you care about.
Whether you are emotionally available.
Whether you are kind when nobody is impressed.
Whether you can be a partner rather than simply a provider.
She may not fall at your feet.
Maybe that is why you should pay attention to her.
The Ordinary Tuesday Test
I think this is where all of this finally comes down for me.
At some point, you have to decide which qualities actually determine whether you can love this person on an ordinary Tuesday.
Not in Greece.
Not at the beautiful resort.
Not when everybody is dressed up and everything is going perfectly.
On Tuesday.
When somebody is tired from work.
When someone had a terrible day.
When dinner needs to be figured out.
When there is laundry somewhere.
When nobody has anywhere exciting to go.
When neither person is trying to impress the other.
Do you still like each other?
Can you talk?
Can you laugh?
Can you disagree without destroying the evening?
Do you feel safe?
Do you respect each other?
Are you still curious about the person sitting across from you?
That is where compatibility starts mattering more than options.
There is no perfect person.
But I do believe there can be someone who fits you beautifully in the places that actually matter.
Finding that person may require something more difficult than having choices.
It may require learning how to choose.
Because being able to get almost anyone you want is not particularly useful if you keep wanting the wrong person.
