After Katy dumped him, Russell was beside himself with regret over not having been a more manly boyfriend to her.  The breakup inspired him to do a bit of soul searching, which led him to type up this letter to Katy.  We assume he slept on it, woke up angry and hurriedly finished it, unedited, before pressing send.  His letter, quite impressively, appears to include all the post-breakup stages of grief: denial, anger, bargaining, depression and acceptance…and then anger again.

Dear Katy,

I just finished reading the book men are from Mars and women are from Venus and I am writing this letter to you in order to express some thoughts and feelings. I get angry you are so unhappy with my personality quirks. It feels like nothing I do is enough to make you happy. I am trying to be more assertive and less clingy and needy with you. It saddens me that my lack of confidence ruined our relationship and that you are not happy with me. I really want you to be happy and I fear sometimes that I will push you away by being me, when all I want is to be by your side. I am most afraid that I am not good enough for you and that I can’t make you happy. I’m sorry I lacked the courage to express my feelings and didn’t listen to your warning when you told me you wanted me to be more assertive and less clingy and needy. I’ve always been afraid to take charge and everyone has told me this including yourself. You have given me on more than one occasion the talk about my potential and how I need to use it. The truth of the matter is that I am afraid of failing, I hate trying my best and the realizing my best wasn’t good enough.

I live with so much regret, but one of the biggest regrets is taking you for granted, believing you would be with me even if I refused to be assertive, clingy and needy. I am truly sorry for being such a jerk and opening my mouth without thinking. I am sorry for not being more assertive and being the man when you were scared and needed me to take charge. In hindsight, I should’ve listened to your fears, reassured you that everything will be fine and that you will do an excellent job.  Katy, I love you so very much, I have never loved anyone as much as I love you. I want you to be happy, I understand you want space to sort out your personal things. I guess I am guilty of not knowing what to do and hiding in my personal cave hoping. I know you told me in the beginning you have baggage and you are not “touchy feeling” person. I realise that you don’t want to be my girl friend and even when I am assertive and not clingy or needy there is a very slim chance you will take me back.

I have accepted this and I have also tried very hard to avoid having ex sex with you because I love you too much and seeing you makes me hurt all over. You used to call every night and recently you have stopped calling and texting after you got drunk the last time we were together and told me you wanted sex. I honestly think you don’t know what you want becasue one minute you say you want space then another you’re all ovr me looking for reasons to stay with me. I know this letter will never reach you and this is really more for me to finally get down on paper what I am feeling. I will always love you and I remember one thing I told you from a movie I once saw “I want you to be happy in life with or with out me, you deserve the best and I wish you well”. But evena s I write this letter and tears are flowing from my eyes I after I hit the send button and delete all the pictures I hold no rancor nor do I wish to see you again. All I wish is to bid you adieu ma belle.

J’t’ame, Russell


“She Bit Me!”

January 8, 2009

Backstory: After many dateless months, Bobby finally met Whitney.  The two met at a NYC bar and immediately hit it off. Soon, Bobby mustered up the courage to ask Whitney out on a formal date.  He consulted all his friends on the best restaurant and where to go for after dinner drinks.  Once he settled on both venues, Bobby actually walked the distance from the restaurant to the bar to make sure it wouldn’t be too far for Whitney to walk.  His best friend, eager to find out how the date went, found this email from Bobby the next morning:

date: Friday, Jan 27, 2007 at 10:20 AM
subject: last night


Oh, instant messaging. It’s got all of the permanence of email, but with the added bonus of being completely off the cuff. The result: your stream-of-consciousness IM that refers to your new Ex as a slut-face-douche-nozzle gets recorded onto his or her computer for all time. For example, here’s one tense (and really long) instant message transcript between “RoMont01” and “JulCap13,” who had met on an online dating service, after they had their first and last phone conversation. Read a highlight below; get their full conversation, from start to finish, after the jump.

JulCap13: well then I guess it sucks to be you…plus I like guys that dig me more than you did
JulCap13: that’s ehat i was going to tell you
RoMont01: Then maybe it’s best that nothing more transpired, anyways. And thus, it doesn’t suck to be either of us.
JulCap13: nope it still sucks to be you

Read the rest of this entry »

In Summation, OMG.

October 17, 2008

Backstory: “Mary” and “Kevin” went to law school together. She thought that they were just friends, but over time it became apparent that Kevin was interested in something more. His interest in Mary grew to an unhealthy obsession, but Mary repeatedly told him that she had a boyfriend with whom she wanted to stay. One night, when Mary was out of town visiting her boyfriend, Kevin sent Mary a series of instant messages saying that he would commit suicide if she didn’t agree to date him, and that the only thing that would make him feel better was if he had a girl around. The next day, Mary received this email:

Subject: OMG

Ok…so I had a few too many drinks last night. Let me preface everything with that, and then go on to comment that I was just messed up a little bit more because jury selection had just started for [Kevin’s late friend’s] murder trial. So yeah, I was just really drunk, combined with a reminder of him, and that made be ridiculously melodramatic.

As far as my other comments…I was drunk. Haha. Let me assure you however that a general rule of operating procedure is that you don’t tell people that you used to be interested if you are still interested. I’m not sure I made that caveat last night, but it is a necessary, and somewhat important caveat. My comments in this venue were of historical significance only, and had no forward-looking content.

In summation, ignore everything said last night.

Backstory: The torrid affair between “Patrick” and “Stacey” began with them as best friends. After kissing one fateful night, Patrick broke up with his girlfriend, and Stacey and Patrick tried to make it work as a couple. After four months of an intense long-distance relationship, however, Patrick dumped Stacey and got back together with his Ex. Patrick and Stacey stopped speaking, but they couldn’t stay away from each other for long. Patrick left his Ex–again–after cheating on her with Stacey–again. He told everyone, including her family, that Stacey was “the one.” Yet as soon as Patrick returned to law school, he started dating someone new. Stacey was furious. She told Patrick that she was too hurt to continue being his friend, which made him angry at her in turn. This email from Stacey followed:


i just can’t do the fake friends thing right now. like i feel like you want me to be able to just turn off everything and be back to besties circa 1L, b/c that’s what fits comfortably into your life right now. i can’t do that via email and i def. wouldn’t be able to do it in person. and i find it really insane that you would even expect me to want/be able to do that. this situation is bizarre and far from ideal, but there’s no way around it except to just sort of block it all out. i don’t want to know what’s going on with you, because it hurts, and it also really pisses me off when i think about how i let myself get dragged back into this just to be so easily discarded by you again. i thought you would have been a tiny bit more thoughtful this time around about what you said and did with me, but i guess it never really was/is about me at all. which is apparantely a lesson that i just can’t seem to learn. i have plenty of questions about what all that bullshit in december was about. was it about just getting a guaranteed fuck? or was a shred of that trying to be a better person stuff actually true and you just couldn’t pull it off? i hope it’s the latter, because i’d rather think that you are just weak rather than cruel. unfortunately i think it is probably the former though. to mess with me that way just to get laid is beyond low. i don’t know if i did something to you somewhere in our relationship to deserve this treatment from you, but it seems completely pathological how you have absolutely no regard for me at all. it is scary to see that this is how you treat someone that you claim to have loved– or even liked for that matter. or maybe the more you care about someone the worse you treat them? who knows. that’s totally fucked up. we’re both people who have pretty major issues and insecurities. the difference between us is that my shit fucks up MY LIFE, whereas your shit completely fucks up the lives of other people. i’m jealous, i wish that i wasn’t the sole victim of my own insanity; i think it would be a lot easier to just fuck up other people’s lives and keep on plugging, thinking it’s all justified. good for you. bad for me. and your next g/f (victim).


Backstory: The recipient of this email, “Amber,”  had feelings for her friend, “Monty.” He liked her as well, but he was already in a relationship with someone else. After realizing that M would not leave his girlfriend, A told M that they could no longer be friends. This email followed.

Dearest Amber –
It’s 4 am and sleep is nowhere in sight right now. I apologize in advance for the disjointed nature of this note…I’ve been trying to get my head straight since you left, to no avail. I didn’t expect this evening, and I am still reeling from it, trying to get used to this. I haven’t felt this low in a long time, but I suppose what goes around comes around, and I know that whatever loss I’m feeling is equivalent, if not exceeded by the emotional maelstrom I’ve induced in you.

The disjointed note continues…

Sunday Morning

October 2, 2008

An attempt to schedule a leisurely afternoon date gone horribly wrong. Sent by “Alan,” 10:00 am:

Since wed or thurs I was always under the impression that we were meeting on sunday. As a result, detailed communication as to my whereabouts didn’t seem necessary.

Sent by “Sara,”  10:30 am:

Sure, Thursday when I asked you to make plans, it was ‘Sunday’ with no specificity therein.  But since last Friday I was under the same impression for last Sunday; you complained that I do not make myself available to you (despite the fact that I don’t recall a single instance that would verify your complaint), so I chose to prioritize seeing you over studying or getting to know my new roomate in order to make ‘it’ up to you.  I don’t fault you for it never panning out, but rather for not telling me until well into the evening that you had to work, despite all my emailing / calling / texting you throughout the afternoon.  I don’t care for being under the same ‘impression’ this Sunday as last, especially when it is abundantly clear that you relegate me to your lowest social priority, to whom communication about when you would like this person to be umpteenly availiable to you ‘didn’t seem necessary’.

Sent by “Alan,” 11:30 am:

That’s a lot of drama for a sunday am. I hope you feel better now that you’ve got that off your chest.

Considering that you feel I’ve put you to my lowest social priority, I think it’s best if I remain cosistent and suggest you make other plans this evening.

I’m in central park now and plan on ejoying the rest of my sunday morning with a book. I’m turning off all means of communication now.

Shit, D

September 17, 2008

Okay, I’m not going to act any different to you – seeing that I don’t really know what the problem is anyways. But the awkward feeling between us a couple of minutes ago kind of says that you have something you want to say to me. So if you don’t even want to talk anymore, tell me, but if not, then let’s not pretend like nothing’s wrong. I’m confused, that’s all.

1 month later

Okay, what did I do to make you so pissed off at me? You wouldn’t talk to me on the street and you won’t talk to me now, that’s rediculous. I don’t want to leave on a bad note beause I think you’re pretty cool, but if you do, then that’s what’s going to happen I guess. I just hate this open-ended shit. Can we talk to you before you leave? If not, then that’s a bummer, but I’m goin to bed, and I think you’re leaving tomorrow, so hopefully I’ll talk to you soon…

20 minutes later

okay then. I guess that’s that – but just know how awful I feel and how much I would like to say I’m sorry, but I know that I can’t do anything to fix this…I’m not trying to say that I didn’t say anything, but blitz takes everything out of context…Shit D, I really fucked up this time, I wish that sometime in the future you can forgive me for being immateur like that…I’m so sorry for being such an asshole. I seriously say it when I mean that I’m gonna miss you