When we started documenting the phenomenon of guys who deal with rejection by sending bizarre, overlong, passive-aggressive emails to women they've gone out with once, we figured it was restricted to brokers and investment bankers. Until an anonymous tipster forwarded us these emails from a tutor who's been emailing her for seven months — after only one date.

Our tipster, a writer and journalist, says that the tutor was "totally normal" when he asked for her number at Starbucks, and that their first date went well. It didn't start to get really creepy until, when she told him on the phone she was in a Starbucks, he insisted on meeting her there because he was "in the neighborhood."

But let's start with the first email — sent unprompted after he Googled to find her email address.

We meet at Starbucks. He asks for my number, I pass it on.

We go on one date. It goes well initially, at least on first glance. He even brought flowers.

Then..he starts calling. I respond back initially. Until he googled me. Finds my e-mail address, and sends the first e-mail.

date Wed, Jul 27, 2011 at 12:57 PM
subject Hey.


Since I can't call up right now, I thought I'd send this e-mail. How are you doing? I hope your day's going well. Just wanted to say that I'm really looking forward to Saturday, especially seeing you in that dress you mentioned.

I'm spending the morning with my dad. I don't really have any plans, just sort of a day of leisure. I'll probably work out a bit, and maybe write something. What are you up to today? I know you have those blogs and ghost article to write. Is there any way I can find the latest articles your writing online? I really admire your writing, and I'd love to keep up with your work.


I tell him he's creeping me out that he found my e-mail, especially since we were talking by phone. Also that he mentioned an essay I had written about an ex-boyfriend on our date. Just awkward.

Then the flurry of e-mails start. I'm no longer comfortable going on the second date, but I decide to give him a chance anyways. Then he keeps e-mailing. Then he texts and leaves voicemails. I ignore, since I'm working.

On Wed, Jul 27, 2011 at 9:13 PM, [REDACTED] wrote:

I don't know if my messages are getting through to you or not, but I just wanted to say that I'm still looking forward to the date, if you'll still go out with me. I'm okay with keeping in touch a little less.

date Wed, Jul 27, 2011 at 9:32 PM
subject Restaurants and dresses.

Hey just to be clear when you were asking about the restaurant with regard to wearing a dress. The restaurants are nice, but they're not SUPER fancy, so when I was telling you I'd like you to wear a dress it wasn't like an order or anything like that. If you feel like dressing casual that's fine too.

The e-mails continue. Then when I call him back, since I'm taking a short walk around the block, he calls. I pick up. I say I'm walking around the neighborhood — he says that he happens to be in the neighborhood — can we meet up? I had mentioned I was in Starbucks at the time. I say no.

The e-mails continued. In between the e-mails, he was begging to buy me lunch, or coffee, anything to get us to meet up. At this point, I no longer feel comfortable going on the second date, and cancel the second date. Then his e-mails continue.


I don't think you're being honest here. But in the off chance that you are I would suggest you pull down your e-mail off of your public website if you don't want people too occasionally find your e-mail, and send you messages with it. I mean it's not like I'm a hacker who discovered your e-mail through some nefarious means, you put it out there for the world to use to get into contact with you.

I am not saying that I was right to use it to contact you without asking (in fact I've apologized for it several times and would again if I thought it would do any good), but I feel this reaction is completely ridiculous.

I think your over worked, over caffeinated, and under slept, and not making a rational decision here if you honestly believe that I was in any way pressuring you to move fast into something you weren't comfortable with, or that I am obsessed with you or whatever it is you feel the problem is.

I mean I think your beautiful, smart and charming. It's a good trifecta you were blessed with, but I would think me noticing that would be a good thing. Assuming that's what your problem is, which I can't even say for certain. This e-mail you sent certainly doesn't clarify anything. I don't know if you imagine that somebody even Sherlock Holmes could read it, and know what you're talking about.

On the off chance that you are not being honest, and this is just a reaction to us not clicking well, via personalities, your attraction to me, or the kiss we shared, or something, that would at least make sense, and I wish you could have found the courage to be more honest and direct about it instead of pulling this.

I really do like and admire your writing. I am really a little jealous that you are making a living off writing, which is something I've always wanted to do. I was hoping that we would at least be able to stay friends, but I don't see that happening even if I wanted it to.

You say your "put off" with my "behavior," like I'm some kind of misbehaving child, and it's not the first time you've been condescending toward me over the internet. I feel like that's my line. I'm put off by your behavior, but I damn well wouldn't have canceled our date over it though.

Anyway, we're definitely gonna occasionally see each other in Washington Heights since you live a block away from my parents. I don't want you to worry about me confronting you in the street, as it seems obvious to me you wouldn't be as comfortable having this conversation in person as over e-mail. As far as I'm concerned this is over. I won't come up to you. I'll pretend you don't exist.

Best of luck to you too, even if I am angry I do mean that. Last Friday was a good day for me, and I'm glad I had it even though I nearly melted in that stupid outfit, and I spent the next few days paying for it with the blisters from those damned shoes. It was a good day for me still, and I hope that it was at least half as pleasant a memory for you.

Now if you'll excuse me, I'm gonna go play rugby and get drunk and howl at the moon.

Best of luck,

Over the next few months, the emails kept coming.

date Mon, Aug 1, 2011 at 10:17 AM
subject One last apology,

I just wanted to say I'm sorry one last time for my part in ending the us that could have been. From the recent lack of contact I feel like I should take the hint that you may not want to keep in touch at all. Which is okay. If I'm wrong look me up sometime. If not, do have a nice life.

date Tue, Aug 2, 2011 at 8:54 AM
subject taking off for a bitr

Know that last email probably should have been the last. This one actually will be it. Sorry about that. Probably shouldn't have bothered, but felt like letting you know I'm leaving town today.
Seeyaround [REDACTED].

date Wed, Aug 24, 2011 at 2:13 PM
subject Back in town.


I know I keep saying each e-mail I send is the last. I think this one will be it though.

Just wanted to mention I'm around again. Thought of you the other day when a Sara Bareilles song came on my Pandora station, and here I am writing you agaion, perhaps reaffirming your correct decision to be rid of me. But I just wanted to mention that I'm around in case you want to keep in touch in any form. I feel badly about the way that I acted, although at the same time I don't know if I fully understand what I did wrong.

So anyway, take care.


He's still e-mailing me even today, which is January 18th, 2012. This first date he spoke of happened July 22nd, 2011.

date Sat, Jan 14, 2012 at 4:09 PM
subject Hey Again,

Hey this is [REDACTED], taking one last shot at keeping in some form of touch.

Would you like to hang out sometime in the most platonic possible sense? Let me know, if you're still in the city. Or even if not.


[image via Shutterstock]