113. Why disappointment is normal & how to keep going

If you have children, you’ve probably experienced entitlement.

It can be maddening, but it’s part of growing up and hopefully it passes.

But I see a lot of entitlement in the dating space.

I think the prevalence of Disney movies, romance novels, TV and chick flicks contribute to this.

We know these things are just entertainment and we don’t consciously mean to internalize them the way we do, but it’s clear to me that a lot of us feel entitled to things that just aren’t realistic.

A wonderful romantic relationship with the man of your dreams is one of the most amazing things you can experience in this world, but it is not your birthright, no more than winning the lottery, the olympics or being a CEO is your birthright.

These things may be possible for you with work and persistence, but you are not entitled to them simply for existing.

And in case you haven’t noticed, most people don’t have these things.

What you’re going for is kind of a big deal.

Now, I happen to think that having a wonderful romantic relationship is one of the easier things to get (compared to winning the lottery or the olympics) but it’s still going to involve some work.

Probably a lot.

I suggest that if you really want to experience this, you make your peace with it and roll up your sleeves.

Things you think you’re entitled to but aren’t:

Meeting the love of your life with ease

It’s work to go out and meet people. It takes time and effort. And they’re not all going to be amazing or interested in dating you and that’s ok.

Having a hassle-free dating experience

Drama and hardship can be minimized by learning basic dating skills, but it can’t be completely avoided. You will have bad phone calls/dates/experiences. You will get stood up, ghosted and pull in a few wingnuts. You are playing a big game here and this is the price of admission.

Don’t go to pieces when these things happen. They are normal. You are a grown woman and you are going to be ok. Dust yourself off and keep going for what you want in this world.

Finding a guy who has all of the qualities you desire who also wants to date you

If your list is on the long side (more than 10 traits) and has superficial qualities on it (like height, income, fitness level) you will likely get 70-90% of what you want. Make sure it’s the RIGHT 70-90%. Holding out longer is generally a terrible idea because time is not your friend in the over 40 dating space.

A man who checks all the boxes perfectly

He calls in advance, always makes a reservation to a fabulous restaurant, buys you flowers, is attentive but not clingy, and generally reads your mind. These men don’t exist. Start working on aligning your expectations with reality.

Having a perfect relationship without effort

Even when you find a great guy there will always be some work involved. And that’s ok.

I’m not trying to scold you here. I KNOW how hard it is out there and my heart goes out to you. Dating is not for the faint of heart and you will get your butt kicked sometimes. I want to normalize this experience for you so that you won’t lose heart or quit when the going gets tough because it will.

And when it does, I want you to remember that this is 100% normal. Nothing has gone wrong. Your guy is still out there looking for you and likely going through his own struggles. If you keep showing up, he’ll be able to find you and you’ll both be so glad.

I don’t want you to think for a second that any of these things means that it’s not meant to be for you. Love is meant to be for you, simply because you want it. And you will for sure get what you want if you keep learning from these experiences and don’t give up.

It’ll be a lot easier for you if you question all your beliefs about what you’re entitled to.

I have a great resource to help you write an