Rejection letter

One of my favorite scenes from You’ve Got Mail. Yes, it’s cut short. *Sigh*

So today, I was faced with the unpleasant task of having to write a rejection memo. Now, as much as I write and draft key messages and manage relationships for a living, turns out I’m absolutely awful at crafting the perfect rejection letter.

This morning, I received this Facebook communication from Topher (who I am not Facebook friends with):

hi irene~

im sorry, but i just have to ask… would it be ok if you can tell me why you chose not to speak to me anymore? I respect your privacy and wishes, and i promise u that i will not contact you anymore going further.

Take great care irene, and wishing you the best!

NOTE: Now, I thought this was a gentlemanly thing to do, given that my ignoring men in the past has wrought reactions including: “Well, don’t overrate yourself, but I wasn’t that into you either”; a bullet-by-bullet analysis of “Then why did you do this? Why did you do that?”; and a tear-jerking “But I thought that night was special to you, too!” Apparently, my guy friends beg to differ, with descriptors including “petulant,” “desperate,” and “kind of a sore loser type of thing.” Now I’m sort of confused.


The message hit a chord with me. One, I had been on two dates with Topher and had hinted at the possibility of a third — although I’d also realized after Date 2 that I had no interest in embarking on Date 3, in part because of someone new that I’m seeing. Two, I was well aware of the fact that I had ignored two series of texts from Topher, and had also rather flippantly ignored a phone call from him yesterday (in my defense, I happened to be brushing my teeth in the bathroom, so I figured I was at least partly justified). And Three, I had not informed him of my lack of interest in attending Date 3.

Pangs of guilt rattled my conscience as I berated myself for not contacting him sooner. I immediately hit the new document command on my word TextEdit and banged out my first attempt at civil, straightforward, and nice:

Thanks for your message. I’m sorry I didn’t get your call, but know that it was because i was busy and not me trying to intentionally avoid speaking to you.

I did have a good time with you both times we met, and I think we would be great as friends. I hope you don’t think I was leading you on.

I hope you’re doing well.

I glanced back over the note. I frowned.

Picture me then slamming down on the backspace button like in the clip above.

My confidence in my rejection letter-composing abilities was pretty much shot at this point, so I decided to call up Sander — who you may remember was the friend I also hit up to rant about Fred.

“quick boy question,” began my IMs. “guy that i went on two dates with and decided not to date just msged me this letter. am i obligated to respond?”

Sander: you’re never obligated to respond, but it says something about you as a person
i personally would just be like “i got caught up in things and have been busy with other friends”
and if there’s a big event i’ll be at, maaaaaybe tell him to come by with his friends
that way you’re nice but you keep the ball in your court… although it’s clear you’re not interested in doing anything with it anytime soon

me: i don’t know… that seems a little too vague.
plus friend zoning him sounds cliche
and isn’t any invite a kind of lead-on? like, isn’t it better to just cut things off and be cold once, than to leave things hanging?
what about
“sorry i haven’t been in touch, got your call but honestly forgot to respond. i had a good time with you, but just don’t think that i feel that way about you. i’m open to being friends, but don’t think i can offer you more than that”

Sander: that sounds even more hopeful that what i proposed

me: apparently whenever i try to be straightforward
i end up being more nebulous

Sander: haha maybe because you veer away before hitting the nail on the head
that would be infuriating for the recipient

me: true..
more straightforward?

Sander: i donno… for some reason, rather unlike me to say this, but it may be better to be vaguer and leave on a friendly, positive note

me: what about
“hi topher, i got your correspondences, but didn’t respond because i needed a some time to think. i did have a good time with you both times we met, but realized that while i am open to being friends, i just didn’t feel that a romantic relationship would be a possibility. i hope you don’t feel that i was being cold toward you — i just wanted to make sure that i was sure about the way i felt and to be honest in telling you. but thanks for reaching out to me and for being such a gentleman during our hangouts.”

Sander: well that’s far too much explanation
do you really want to leave yourself so vulnerable to interpretation? he’s so totally going to show that msg to someone else
if you just want to be cold and cut if off, just cut it off in a more concise manner

me: isn’t that pretty clear?

Sander: too clear!

me: oh.

Sander: well reread what you wrote above
you said ‘correspondences’ and analyzed the possibilities for romantic relationships (0%)
and then said you’d CONSIDER being friends with him
if he wasn’t a bad person, i wouldn’t drive a stake through his heart and dignity in one fell blow

me: oh.

I clicked out of my conversation with Sander and sat there, staring at the computer screen, tapping my fingers with increasing intensity for a few minutes. Then a lightbulb switch went on over my head. It was the perfect solution!

I procrastinated.

Here’s some testament to not being a lazy heartless bitch and answering letters like Topher’s on time. Not one week later, I’m at Marquee, which in my opinion is one of NYC’s shittiest nightclubs, especially given that it has so much potential, but so little to actually give. And the douchiest Asian wangsters. But the new boy I’m seeing asked me there, so I made the appearance — however begrudging — there.

Now, granted, I actually ended up having a decent time at Marquee, especially since I spent the vast majority of my time happily smooching away with the new boy. We briefly surfaced for air just long enough for new boy to suggest we grab a drink, made out some more, then finally made our way over to the bar. Once there, we dug our way through the crowd and ordered our drinks, new boy standing with his arm around my waist.

I felt a bump on my left arm and instinctively glanced over.

“Oops, sorry,” I said.

“No problem,” a voice replied.

We both looked up at each other.

“Oh.” I held up my hand and gave a polite wave. “Hello.”

Topher looked back at me with an eyebrow raised. “Hey.”

I turned around to look at new boy, eyes wide and frantic, tapping my fingers on the bar counter with increasing intensity. When the drinks we’d ordered finally arrived, I quickly downed my drink and grabbed new boy by the arm, saying, “We need to leave immediately.”

2:02 “We have to get out of here immediately.”

The next day, I knew that whatever good or otherwise intentions I had had before were and would be tainted and completely negated now that I had had the uncomfortable run-in with Topher out in public. But Sander’s words stuck in my mind: “it says something about you as a person.”

So all I could do was administer as much damage control as I could:


I should have responded to this message as soon as you sent it to me, but then I started pondering the “right” things to say and the “right” ways to say them, and I fell behind a little. Then of course we ran into each other on Friday, and I think I made that moment much more awkward than it should have been.

In the spirit of being honest, I want to start out by saying that I really did — do — enjoy hanging out with you. But while I think conversationally we get along fabulously, I just didn’t feel that connection with you that made me feel that I could see myself in a relationship with you. So I felt incredibly guilty about mentioning a third date, even though I already knew how I felt about you — for that, I apologize.

I should have taken the initiative to speak to you about this candidly, but I confess that I allowed myself to get swept up in my other daily responsibilities like work and social commitments to delay doing the right thing in a more prompt manner. That said, I do hope I’ve conveyed my sentiments without sounding contrived.

Thanks for being understanding, and I really hope you find what you’re looking for.

Turns out that all I needed was some procrastination-derived adrenaline and lowered standards to finish the dirty deed. Needless to say, I never heard back from Topher — not that I’d believed rather hastily pieced-together confession of guilt had warranted a response — but I ventured to think I had made my best attempt at candor and non-hackneyed prose.

What do you think of the letter I ultimately sent? What philosophy(ies) drives(drive) your rejection letters? How would you have written yours differently in this situation?

And also: vague, clear, or too clear?


2 thoughts on “Rejection letter

  1. more vague in the beginning, then clear later.

    hopefully if the guy has some experience w/ dating.. being vague (don’t accept their offer next 2-3x of going out, keep your text replies short, etc) is enough to let them know you’re not interested by not having to give a blow to their ego with a list of “why I don’t like you” bullet points… if they’re aggressive or keep asking and won’t leave you alone, then I’ll go with the more clear explanation so they don’t waste their time..

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