My #1 regret in life

Apr 25, 2024 12:31 pm

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My #1 regret in life: I wish I had taken myself and dating more seriously in my 20s.


Because having a great life partner is one of the BIGGEST life upgrades you can make.

Today, I want to share 8 pieces of Brutally Honest relationship advice that I’d give to my younger self (so you can avoid my mistakes):


1/ Improve yourself

You have to love yourself before you can expect someone else to. 

And if you don’t, it’s a BIG ask to imagine a person will love and fix you.

The best way I’ve found is to focus on the things under your control:

  • You can control your effort
  • You can control your hobbies
  • You can control how you dress
  • You can control who you hang out with

These things don’t guarantee someone will show up on your doorstep like Uber Eats but they guarantee you’ll like yourself - and I promise over time someone else will like you too. 

2/ Be binary about what you’re looking for

When you ask people what they want in a partner, they all say the same things.

“Funny. Attractive. Sweet.”

Cool. But a lot of people are those things. 

Here’s what works better, have binary filters:

• Kids or No Kids?

• Jewish or Not Jewish

• They want to live in Barcelona

Super black and white.

Having more clear filters makes saying no much easier. 

3/ Be where the fish are

Initially, I thought dating a Jewish person was a big requirement for me.

So I went to Israel. LA. New York.

But after dating a few Jewish women, it turned out that being Jewish wasn’t a big deal to me.

The lesson is the same when you’re marketing for your business.

Meet your customers where they are.

My friend went to Colombia to find his wife. I met my wife in Barcelona.

Where does your ideal partner live? Where are you?

4/ The Dinner Test

A while back, my brother asked me a question that I still remember to this day.

He asked, “If you couldn’t have sex with that person, would you still be with them?”

And for all of my past dates, the answer was “No”.

This sheds light that you have to like your partner mentally. 

Realize you will have at least 1,000 dinners with them.

It’s important that you genuinely enjoy being with your partner, you’ll be sharing many meals together.

5/ Don’t settle

A while back, I got engaged to a girl because everything was moving in that direction. I thought that was what I was supposed to do.

But then my business partner Chad asked, “Are you getting what you’re getting or are you getting what you want?”

And boy did that hit hard.

Let me repeat that again…

Are you getting what you’re getting or are you getting what you want?

As adults, we often let society's norms and expectations drown out our intuition.

Go to college. Get good grades. Get a ‘safe’ job. Work 40 hours a week in a boring cubicle. Work until you’re 65+. And save your best adventures until retirement.

But deep down inside, we know when we’re settling.

Now, I constantly ask myself, “How did I trick this woman into being with me?” I feel so lucky to be with Mafe.

6/ Learn the art of being alone

After college, I got cheated on. It destroyed my self-worth. I felt unlovable. Why would anyone want to be with me?

It took me a long time to be comfortable with myself again.

It’s a skill.

• Eat a meal alone

• Go for a walk alone

• Go to the movies alone

Can you be happy with yourself without distracting yourself with alcohol or social media?

The best relationships are when two WHOLE people decide to be together. Not two people who just don’t want to feel lonely.

7/ It takes time to figure out what you want

In your 20s, date a TON of people.

It sounds obvious, but it takes time to figure out what you value in a relationship.

In business, when we're recruiting, we rarely hire the first person we interview.

It’s like going to a buffet. The first time you go up for food, you try a bit of everything. The second time, you know what you like and get more of it.

The same goes for dating.

You have to go through a few dates to figure out what you do and don’t like.

8/ Partnership is #1 life upgrade

Years ago, I thought dating many people was more fun than just one person.

But once I truly committed to taking dating and myself seriously, it took six weeks and then I met Mafe.

My friend said, “If you want variety in dating, date one person.”

What does that mean? Well, when you go on lots of dates, you end up repeating yourself.

• These are my hobbies

• Here’s my funniest joke

• This is my background story

But when you truly get to know the textures and flavors of another human being, that’s special.

Go wide, then go deep.

Rooting for you,

Noah 🌮

Ps. I like to say Million Dollar Weekend is a personal transformation book disguised as a business book. While it won’t teach you how to find your loved one, it will help you overcome your fear of starting and your fear of asking. Check it out! 💚