I Don't Know How to Break Up With People. Help! – Kveller
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dear gefilte

I Don’t Know How to Break Up With People. Help!

Dear Gefilte,

I am a 44-year-old, straight, single male. I still hope to meet someone with whom I’ll spend the rest of my life. I am not afraid of intimacy; I am not afraid of rejection. What I am afraid of is having to reject other people. 

I know this keeps me from“getting out there.” Even on a first date, if a woman is clearly interested in a second date when I’m not, figuring out how to say good night is an anxious and awkward affair. When it comes to breaking up with someone I’ve been dating for a few months—disaster. Friends try to assure me that no one is good at breaking up, but for the record, I am truly not skilled at it. I get so anxious about it that it invariably goes terribly, and I end up feeling awful about myself.

If only there was a breaking-up training program… I mean one that didn’t actually involve dating people. As it is, I’m much more inclined to stay home alone comfortably watching a movie than venturing down a path that might lead me to a place where I have to reject someone.

Do you have any advice?

Unattached, Inept, and Intimidated

 Dear UnInIn,

Before I weigh in on this, there are a few perspectives I think you need to hear:

What, you’re too good for us now?

-Your abandoned couch cushions

If you start dating again, how am I going to cash in on all those DVD residuals?

-Julia Roberts

How about all those lonely Saturday nights when I gave you free delivery even though you only ordered a low-sodium entree and a Fanta?

-Charlie Peking, owner of Peking Charlie’s

You see, Mister UnInIn, you are saying NO all the time. You just have to accept that. And with all due respect to you and Julia Roberts, your NO is not that powerful. It’s the waffling or dishonest YES that’s always more destructive. And staying home to stew in WHAT IF…? doesn’t help anyone, either.

Here’s a smarter person talking about this same idea:

Go not to the Elves for counsel, for they will say both no and yes.

(Thank you, J. R. R. Tolkien.)

Make no mistake about it—saying NO is a skill. One that I’m still doing gefiltesthenics to cultivate every day, because once again, it comes back to kickboxing your fears. Fears about slamming doors shut in windowless rooms, fears about being unloveable or undeserving of love, fears about NO leading to nevermore, nein, nada, or nowayjoseyoulostyourchanceforever.

I have spent way too many years being scared of the word NO. I’ve held onto jeans that cut off circulation, relationships that cut off honesty, and the Le Sportsac my mom carried to the hospital when she died—just because I thought I needed to preserve these as artifacts of possibility.

The first time I remember actively saying no was a painful experience. My mom was already in the “not sure what else we can do at this point” part of her cancer treatment. I had just come home from across the country to be with her. I’d brought my freckled boyfriend with me. One morning, he asked me to get scrambled eggs at a diner with his uncle and then go check out the apartment we were going to rent. My mom said she wanted me to stay home instead.

I said no to her.

A week later, she was dead.

UnInIn, it’s taken me over a decade to shove that space in between those two sentences. I spent many days, nights, and therapy sessions thinking I killed my mom with that NO.

I didn’t. Disease killed her body. And as far as I’m concerned, her spirit swims on.

What I see now is that I should have practiced saying no to her in my teens or even early 20s so we could find a way to disagree and come back together. But as I said, I was too scared of that two-letter ogre. And much too scared of shutting my mom out of my life. So I slept with the door open and a nighlight on and I waited until I was 30 and my mom was about to take her last breath before I let us both experience this. Maybe it was my way of helping us both let go. That part is still up for debate.

Here’s a darkly beautiful quote from the late and great David Rakoff:

I will forever be grateful to my oncologist for opening the door and saying, ‘Damn it, the tumor’s 10 percent bigger,’ before he even said hello.

Listen, this magically nasal monosyllabic word is never going to be sexy, cute, or particularly fun. But it is neccessary, and liberating.

So let’s hop on the lifeboat called NO together.

I have a fun assignment for you and me, and whoever wants to play along at home. It comes in three parts (because I can’t say NO to any of these activities):

1. Clean out your closet and give away five things you don’t love

2. Make a list of things you find easy to refuse (I’m talking about you, mayonnaise-flavored skydiving!)

3. Reach out to someone who said no to you at any point and thank her/him.

To dare is to lose one’s footing momentarily. To not dare is to lose oneself.

Søren Kierkegaard

This is how we make space for spangled culottes, clear skies, and the truth.

With love and schmaltz,


Read More:

My Major Issue with My Son’s Valentine’s Day Homework Assignment

After Divorce, Finding Love

My Son Didn’t Want to Change Schools, But Now He’s Glad He Did

Have a question for Gefilte? Send it to deargefilte@kveller.com, and you might just get an answer. 


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