Ask Jessie: How do I handle a controlling friend?

Dear Jessie,

How do I handle a controlling friend?

I became friends with one of my besties a couple years ago. It’s hard to meet friends as adults and she was a godsend at an office where I didn’t quite fit in. She was all in from the beginning, always there whenever I had a crisis and willing to give the shirt off her back.

For the past year or so, however, we have really struggled. We have SO much fun together and she often feels like a partner in crime, but there are a lot of moments where she acts strangely.

For example, there’s always this feeling that I owe her for the times she was there for me in the past, she gets really offended if hang out with other people without inviting her, and she either tries to talk me out of goals or ideas I have or decides she wants to do it with me (e.g., I quit the job in our terrible office and moved to my dream city and she decided to do the same thing six months later, even though she had never been here before). Her behavior has only gotten worse since I’ve started dating someone.

I’ve had SO many talks with her about this and tried every tactic imaginable. I’ve asked calmly and rationally, I’ve had mutual friends mediate, and I’ve had screaming matches. All that ever seems to happen is that we find peace for a few weeks until I seem to step in it and the cycle starts all over again.

She’s such a good person when she isn’t plagued by what seems like paranoia and jealousy. Is our friendship salvageable? How do I handle a controlling friend? 


Friendship Shouldn’t Be This Hard

Dear Friendship Shouldn’t be this hard,

I had a friend exactly like this (down to the moving after me to my dream city) and what led to me setting the necessary boundaries was asking myself, “Would I make friends with this person again if I had known this is how she would treat me?” “Would I allow a boyfriend to treat me this way?” and “Why do I stay?”

The first two were easy: no and no.

The truth of the matter is that your friend is just as much the unstable, unsupportive person during the bad times as she is the loving, generous version in the good times.

And I don’t know about you, but those good times never feel as good when you know you’ll be getting guilt tripped about it later.

She’s set you up for emotional debts you can never repay. Rather, what she’s doing is keeping you in her energy through guilt so you can’t leave her for how she treats you.

Instead, you feel compelled to stay until your debt is paid up. Only then can prove to her you’re a good enough friend that she doesn’t need to panic and everything can go back to normal.

Friendship, these tests are never going to end. You will never repay your debt. This cycle will be on repeat until you decide to leave. And, unfortunately, that’s the only solution here.

The second part to figuring out “How do I handle a controlling friend?” is this:

Ask yourself, “why do i stay?”

I really spent a lot of time on that last one when I was living through my traumatic friendship.

What it essentially boiled down to was because I was afraid she would talk shit about me. So, I questioned that fear.

“Our friends know nothing she says is accurate, so who am I afraid she’ll slander me to?”

And it came down to her future friends. Just like she had talked trash about her first best friend leaving her after getting a boyfriend, I was afraid she would say the same things about me to future people.

I was literally holding myself in that relationship bc I was afraid of the opinions of STRANGERS I WOULD NEVER MEET. What?!

I also asked myself about the emotions she elicited in me. Were they recreating a familiar dynamic? What did it make me think of?

My dad.

He’s not an easily impressed man. He was focused on raising strong MEN, including me and my sister. Whether he intended it or not, I always felt like I needed to prove I was worth loving. And I never felt like I could.

That’s exactly how this friend made me feel.

You deserve friends who don’t make you prove your worth

To answer your question, “How do I handle a controlling friend?” is simple: Break up with her.

Here’s how I did it.

I waited for my friend to pick the next fight (literally didn’t even take a week) and I told her I needed a break from our friendship to think. She took that as a break UP because she couldn’t allow me even some time apart.

I felt relieved almost immediately. Part of me felt guilty, but the larger part of me just felt so deeply relieved and at peace.

The month after our breakup, I just felt so fucking peaceful and happy that I knew I would never return. I found out from a mutual friend that she felt the same way and it just made me more secure in my decision.

Even now, three and a half years later and despite all the mistreatment, I hope she’s doing well. Sometimes it’s just easier to love someone from afar.

I never check in or ask any mutual friends about her, but I rest assured knowing (1) this was the right decision for us both and (2) anyone who hears her story of woe that TWO best friends left her after getting boyfriends will see it as a red flag about her behavior as a friend.

Hope this helps. If you would like any guidance on this or anything else, feel free to either book a coaching session or a general card reading to tap into the energy of both you and your friend.

Jessie Da Silva

Craving more from your life & business?
I can help.

After months of largely crickets in my online business, I was able to do enough inner work that I could follow my true calling without fear. Once I snapped into the right mindset and habits, the money began to flow effortlessly. And now I'm ready to teach you to do that, too.

Jessie Da Silva

Make More Money Today
Everyone needs balance to find alignment. Take this quiz to figure out where to focus your effort so you can call in more abundance! Check your email after for free resources.


Submit a Comment

Your email address will not be published. Required fields are marked *

This site uses Akismet to reduce spam. Learn how your comment data is processed.

YOU might also like

Picture of an alter with lavender on it with the words "How I manifested more than 20k in one launch" with Jessie DaSilva written on the top

How I Manifested More Than $20k in One Launch

Today, I want to tell you about one of my biggest money manifestations in business to date: How I manifested more than $20k in one launch. It all started at the tail end of 2020, but came to fruition earlier this year. In the post right before this one, I told you...
Picture of an altar with lavender and the words "how I manifested my dream career" with Jessie DaSilva written over the picture

How I Manifested My Dream Career

People have scoffed at me when I’ve spoken about “manifesting” your dream career or dream business, but it’s only because they’re more familiar with its other names:  Mindset. Positive Thinking. Risk-taking. Leaps of Faith. Saying, “Fuck It” and Doing it Anyway....
Picture of someone on their laptop with the words "Free Resources and Black Friday Sales" with Jessie Da Silva written over the picture.

Free Resources and Black Friday Sales

Hey new and old friends! So you’ve found me on TikTok or Buzzfeed, and you’re intrigued by what it is I do. But you're not sure where to go from here? I'm going to go over some Free Resouces and my Black Friday Deals with you. Which Facebook Group is for you?  5...
A picture of ladies working at a desk with the words "My new Facebook Group is now live!" on top with Jessie DaSilva

My new Facebook Group is live!

Hey new and old friends, so I know I said I was making another BRAND NEW GROUP for those who want networking, job hunt, and career advice and I have good news…  My new Facebook Group is ready!  Here’s the link Check out my Black Friday Sale Offers! I also wanted to...
Picture of Jessie DaSilva with words "I've been featured in Buzzfeed!" on top.

I’ve been featured in Buzzfeed!

Hey old and new friends! I wanted to take a minute to introduce myself on my socials since being featured on Buzzfeed for my viral TikTok content!  I’m Jessie DaSilva, also known as the Millennial Money Witch, a name given to me by Forbes for my brand of coaching...