How To Reject Someone Nicely: A Survival Guide to That Awkward Conversation

“How to reject someone nicely,” is a phrase, I’m certain, the few suitors I did have in high school, punched into their Google search bar.

They would have had the right instincts. I was not like other girls in high school.

But not in the sexy way that would make the hot jock, brush away a stray strand of hair as he lifted my chin and said “you’re beautiful, you know that?” and I–being pretty and not knowing it, unlike other girls, certainly wouldn’t.

This is what I imagine to be the experience of “other girls” on a cool summer’s night. Forever infinite in the zeitgeist of youth! Like a scene from Perks of Being a Wall Flower (a movie I did not see, but reference often).

While at the same time, I, a teenage Danny McBride, was stealing my parent’s minivan and egging my high school at 5 pm in broad daylight. And just like my hero and the greatest HBO TV Character Kenny Powers, my aim was trash, and my high school principal was trying to kill me.

In summary, high school was tough because I was:

1) Four pounds heavier than all my friends.

2) Abused the Facebook status bar.

3) Wore a pink bathrobe every single day.

The pink bathrobe, though not necessarily flattering at the waistline, is the most treasured artifact from my youth.

I acquired the piece through salacious means. I stole it from a Ross Dress for Less, located in the Kihei Strip Mall, on vacation that my parents forced me to go on.

Now that I pay my own rent (and in this economy),I have more appreciation for all-expense-paid vacations.

Though shamefully I admit at the time I felt nothing but hot rage because the four-week prison sentence in paradise forced me to miss Jaime Tobias’ Bat Mitzvah, which was, in earnest, the event of the century.

People were MAKING OUT at Jaime Tobias’ Bat Mitzvah. People that weren’t me. Because I was stuck in the Kihei Strip Mall while my dad bargained for crab legs at Costco, and I updated my Facebook status to: I don’t even LIKE crabs!!! Nobody f**king understands me!! While my mom dubiously swiped her credit card for $9.99 (a steal) at the Ross Dress For Less in the Kihei Strip Mall.

How To Reject Someone Nicely: COMING SOON (but not yet, I’m in the middle of my story!)

I never had a childhood “blankie”, mostly because I trudged out of the womb, warm and full-grown.

As a child, I did not identify with being a child. I thought children were embarrassing; unable to hold up their own heads and forcing everyone around them to spoon-feed them.

Co-dependent narcs.

RELATED: Weaponized Incompetence: How to Respond to the Subtle Manipulation Tactic

My mother recalls, in perhaps the most telling scene from my infancy, that the day I came home from the hospital, I slept through the night. I don’t know much about the habits of newborns, but for all intents and purposes, I deem my behavior very unlike other newborns.

My mother woke up in a frenzy, thinking I’d contracted a routine case of SIDS, but in fact, I was sound in my crib, unbothered by the need for elementary life-sustaining rations of “breast milk.” I exclusively drink coffee (black), how dare they.

My mother took me to the pediatrician, concerned that I was not fiending for her hand-me-down nipple (I’m the third of four children).

The pediatrician sardonically reminded my mother that I was, respectfully, an 11-pound baby, and actually, she should consider putting me on a weight loss plan.

She handed my mother a pamphlet titled: “It’s the mid-90s and we don’t know that calling kids fat from the womb is rude”. And my scared-straight mother got me signed up on an intensive workout program straight away; Gymboree–the baby’s Ozempic.

When I reminded my therapist of this fact– that I was a product of a gestational pregnancy, and therefore never lost that stubborn 4 pounds I was cursed with at birth, AND THIS IN FACT, was the true reason I was going to kill myself- she told me that if being 4 pounds heavier than all my friends was such a big deal, then I needed to get over it and get on a treadmill [paraphrasing]. How dare she.

In a convoluted way, as I reflect on my high school years with full transparency, I can see that perhaps the Ross Dress for Less Robe was a sort of delayed security “blankie”…

I wore it to school despite the certainty of securing a detention slip because of its rebellion against the strict dress code and if I’m being completely honest, my man-repelling, body-shrouding apparel was the collateral from some wrong idea about myself I came up with.

Somewhere in between slapping on my spandex for Gymboree and getting the rug of false hope ripped out from under me, from my first real crush on a popular guy two years older than me (who thought my tweets were funny and swore he was totally breaking up with his hot girlfriend “any day now”).

Somewhere along that jagged line, I really did believe I wasn’t like other girls. They were better and I was worse. They were prettier and skinnier and happier. All my friends were fun and gorgeous and I was “funny” (boo) and undesirable (sad), and that’s really how I felt inside.

Except, it took me 26 years of loving myself to be able to type those sentences.

At 16, I had no concept of any of that sh*t. I just thought no one would ever want to kiss me and instead of being sad about it, and despite my 76% average all of high school, I resolved to join the Mensa International Society–like a Joan of Arc reincarnate in Einstein’s clothing.

These delusions are probably what landed me on my court-mandated therapy visits. And by court-mandated, I mean per the recommendation of my high school principal (who was also the girl’s Volleyball coach and actually had no qualifications to stand at either post).*

In the most horrific conversation I’ve ever had with my therapist — to who I’m now deciding this article — she gave it to me straight one day.

I was going off about how all my friends were out there kissing boys instead of being intellectuals–like her and I.

I said this, clutching my copy of The Complete Works of Plato that I never actually read but carried around with me everywhere, in complete earnest.

“Intellectuals?” my therapist countered.

“You and I” I said, gesturing wildly between us.

First, to my 60-year-old psychiatrist and then back to my 16-year-old self, sitting in my pink bathrobe boldly paired with black Crocs kicked up on her coffee table.

Did I miss something? She didn’t tell me too much about herself, but I was pretty sure she was single too. On account of the fact I Googled her name in the public records and her divorce filing came up and also because single people love to give advice.

After five years of sitting in her office and being told to “stop feeling sorry for myself”, I felt I had a right to know. But apparently discussing her marital issues was a breach of a “professional boundary”, which I apparently “continuously disrespected” every time I searched her name in the public records and also called her my “best friend”.

Though she never said it back, and I’m pretty sure she lied about going into early retirement–beneath her stoic veneer I knew, she was the Robin Williams to my Good Will Hunting.

She said a lot of things I never wanted to hear, but this was one of them:

“You’re not better than your friends because you read“

*GASP! I clutch The Complete Works of Plato incensed*.

– A basically real conversation [2013]

She said a lot of other things I wasn’t a big fan of that session like: “romantic connections and sexual feelings are part of life”, and “one day you will meet a wonderful person” and “get your Crocs off my coffee table”. But all of this was psycho-babble.

A-la-Bella Swan in that dramatic scene in Twilight, of three things I was absolutely positive:

1) I would never have a sexual feeling ever because I would bury them.

2) I would never meet a wonderful person because they didn’t exist.

3) I would absolutely get my Crocs off the table because my 60-year-old therapist scared the f**k outta me.

I was wrong about #2. Turns out the world is filled with wonderful people and I would love at least five of them. (I would come to loathe at least two of them again, but I digress).

We Made It Here–The Point I’ve Been Meaning to Make.

As a living, breathing woman, I have experienced my allotted share of rejection.

From Jude Law at the Toronto Film Festival after-party hosted at the worst SoHo House, to the stewardess on AC Flight 537 with service to Hawaii.

In the case of Jude Law, I think he made a big mistake. I opened with, “I have the same name as your ex-wife” and then tried to crush my Adderall in his cocktail, which totally seems like his vibe.

In the case of the stewardess, I think I made a big mistake pre-drinking for the “event” and then bullying my seatmate to order more gin and tonics for me, after I had been cut off (which was not the covert operation I thought it was, because next thing I know, the impending threat of deportation is suddenly being laid on the tiny tray table).

*a bunch of not-important stuff happened but the moral of the story is don’t apologize for who you are*

Eventually, I discovered the power of a flat iron and contacts and had my very own Princess Diaries moment. After a glorious makeover at the wise hand of my dear friend and MUA influencer @SonjdraDeluxe, who taught me everything I know about being a woman at the MAC Cosmetics Counter– I became like other girls.

I’m thrilled to say, it really turned around for me. A few people wanted to kiss me and because of it, I now I have the pleasure of writing this article for you wherein I chronicle the ways in which I have rejected people, nicely.

And SO after the most adieu — I present to you:

How to Reject Someone Nicely: A Hot Girl + Guy Guide

Because if there’s one thing I learned in all my years of being a human person, honest communication is not just all around cooler, it’s sexier too

A good match is hard to find, okay? You don’t need to feel bad about having standards for a serious relationship or someone you’re going to kiss at least twice.

Though similar to my high school principal, I have absolutely no qualifications–I consider myself somewhat of an armchair expert and dare I say, relationship coach when it comes to considering how to reject someone nicely.

Here’s a little index I’ve put together for you influenced by all my years of therapy (before it was cool).

On Calling, Texting, of Face-To-Face

“To see or not to see, that is the question!”

– William Shakespeare, probably.

I have some hard and fast rules about this one when it comes to how to exit a romantic connection!

The Rule: Face them, always*

1. If you have been seriously dating someone–break up with them in person, bro. Be a man (even if you’re a woman).
2. If you have been casually dating* someone…break up with them in person.

*Casually Dating = if you have seen them for 4+ Saturdays

Okay, I lied. There are no hard and fast rules here. There’s always exceptions.

The Exception: Toxic relationships.

Cut the chord. Text them. Who cares. Chances are they’re not gonna let you break up with them if they can help it, so you just get dragged into the Bermuda Triangle of “Closure”.

RELATED: 5 Signs You’re in a Toxic Relationship, and What Steps To Take Next

The Other Exception: You’re not actually dating.

If you have gone on like, one date– relax. Texting is fine. Don’t be creepy and schedule to see them. To tell them you will no longer be scheduled to see them. Politely decline their advances and move on.

On Break-Up Speeches

In Person/On Phone (because no one actually subscribes to my face-to-face rule): I don’t think it’s ever wise to plan out what you’re going to say too much.

You get tripped up if you forget one of your carefully crafted lines and then you’re all flustered, dragging the beaten dead horse all across the living room floor, while their roommate has their ear to a styrofoam cup against a wall in the next room.

Skip the speech. Have a few talking points. Don’t drag it out.

On Text: Fine. You can draft your breakup message in notes and send it to 10 friends for feedback. I’ll allow it, but I discourage it and here’s why:

1. It’s important to exercise trusting our own intuition and not outsource validation. Your friends/mom/therapist can’t reject someone for you. Manage your own conflict start-to-finish. It’s the most useful skill, honestly.
2. We can make things more dramatic than necessary. Maybe it’s just me, but drafting my text directly in the chat bubble works this psychological voodoo where it forces me to be more honest. When I’m drafting notes, I get it in my head, and feel contrived. Direct chat bubble = I keep it more real and don’t try to get it perfect (which it never will be).

On the “Right Time”

The Rule: There is no “right time” to break up with someone.

Sorry, it’s a myth. It’s always gonna be hard. It’s never a “good time” to hurt a person’s feelings and guess what? They don’t have to like you afterward. They don’t have to want to be your friend.

In fact, I skip even offering this. I think it’s sort of rude to offer the “friendship” consolation prize. Because 99.9% of the time you don’t actually want to be their friend. You don’t mean it. So don’t say it.

And if you do mean it, consider why it is you want to have a friendship with someone who is attracted to you and wants more than that. Perhaps it is so you can create a power dynamic where they are subservient to you. Perhaps not. But also perhaps. (It is).

No judgment. I’ve done it, but when I do, it’s always because I’m peak insecure. It’s not hot to use people. Be hotter. Be better.

The Exception: If it is your birthday and your fiancee picks you up from the office after a long day and you walk into your house together–and all the lights are off, and standing in the dark, you think this is a good time to take the opportunity to say “I want to break up”, so you do, when suddenly all the lights go on and 100 people hiding in your living room yell “SURPRISE” and your fiancee is staring at you heartbroken, mouth agape. This is the wrong time.

On Ghosting

I’m proud to say I’ve never ghosted anyone in my life–because I think it says more about you than it does about them.

The Rule: Ghosting is lame. You’re not too busy to reach out. It takes two seconds. We like to think we’re really important. Like we just have so much going on we forget to be a decent person?

Subconsciously we want to support the belief that we’re so desirable we can’t help but break hearts in every room we walk into (guilty as charged). We think our suitors will never get over us if we end it, so we avoid it, because it’s easier. I’m here to tell you, they will. In truth, most of the time we need to get over ourselves.

The Exception: If they creep you out, ghost the f**k outta them. Block ’em. Ignore ’em. Run if you see ’em! Never compromise your personal comfort to spare someone who (if they are creeping you out) clearly doesn’t care about your personal comfort.

On Sparing Feelings

The Rule: All you can be is honest, nothing more nothing less.

Ultimately, if you are being honest that is the kindest thing you can do, even if the other person doesn’t entirely understand it, and even if they blame you for it.

Sometimes we think we’re doing the right thing by being “nice”, when really what we think is “nice”, actually hurts the other person more in the long run, because it’s dishonest.

They don’t have the full picture, so they can’t make informed decisions. We don’t give them the opportunity to, because we’re being dishonest, because it’s easier than being real but uncomfortable.

At the end of the day, we try to spare people’s feelings because it makes us feel more in control. Hurting people sucks, and being direct is hard. We don’t like being the bad guy in someone else’s story.

On Being the Good Guy

The Rule: Breakups always suck. Don’t try to reinvent the wheel.

You don’t need to be a d*ck, but that doesn’t mean you’re a hero.

Ugh. Don’t get me started on the good guy. Trying to be the good guy stole at least 17 years of my life, ok? Until I finally learned in one of my break ups, it’s not about that at all. In fact, being the good guy is always more about me than the other person.

Being the “Good Guy” in a breakup is often in direct opposition to being honest.

The good guy wants to break up, but needs to still be seen as the good guy while they’re doing the breaking up!

The good guy doesn’t want to look like the bad guy because it makes them feel bad about themselves, because the good guy judges their self-worth through other people’s perception of them. So in avoiding being the bad guy, the good guy avoids being honest, so they “look good” and are “likable”, but their actions aren’t in line with their value system and in the name of “not wanting to hurt their partner’s feelings” the good guy continues pretending to be someone they are not, so they can manipulate their partner into supporting their self-worth.

It’s a vicious cycle.

It’s not on purpose, and we don’t necessarily know we’re doing it, but subconsciously “the good guy” wants to control people’s perception of them, when really what we all need is to surrender and let go–and let the chips fall where they may.

The Exception: When both people are on the same page and want to break up. This is the best case scenario.

On Closure

The Rule: Closure is a lie. Avoid it like the plague.

My favorite quote I’ve ever heard in regard to staying in or getting out of relationships is:

“Are you prolonging life or are you extending death.”

“Closure” is like hooking up a cadaver to a ventilator. Pointless and creepy. Someone always has false hope that there will be a make-up after the breakup. And more often than not, the person who did the breaking up is just waiting to find someone new to come along.

The Exception: Sometimes you really love someone even though you’re not in love with them, it’s hard to let go. It’s hard to release the life you imagined for yourself, that you had with them. It’s scary to imagine a new life without them. It’s scary to imagine starting again on your own or sometimes even scarier–starting again with someone new. That’s okay. You’re doing your best. Hang in there. I promise you, everything will happen exactly as it’s meant to when it’s meant to. As far as I’m concerned, I think you’re doing great.

And if you’re still not sure…

Because I am feeling generous, for the small fee of emailing my amazing editor and telling him how much you love my column (yes, that’s what we’re calling it now), you can DM me on Instagram and I will ghostwrite your break up texts because that’s how much I appreciate you.