You may not believe this letter is for real, but you’ll definitely know you never want to receive anything like it

Personally, I don’t make a habit of reading Gawker. I think a lot of the stuff they write, while amusing, is mean-spirited; their pieces take pleasure in the pain of others. That said, I do occasionally peruse the site. When I saw the headline ‘This May Be the Most Annoying Online Dating Break-Up Email Ever’ I had to check it out. Although the headline would imply that the author, Brian Moylan,  thinks the  dumper [whom is referred to as Oompa Loompa] is a tool, by the email’s end, he was on the fence. So am I.

Read for yourself; we’ll discuss afterwards. The names have been changed; Miss Lonelyhearts is, quite clearly, the dumpee. Get ready to be pissed off, befuddled and relieved…that you were not the recipient.

Dear [MissLonelyhearts],

Thanks for an interesting 3 dates. I spent the weekend thinking about you and me and have decided that I’m not interested in pursuing “us” any longer.

I had a great time on our second date. You did a great job in planning that night. Thank you again! I really enjoyed meeting your friends on Friday night and they were great to talk to.

Personally, I’m not a big fan of when people just disappear, fall off the map or suddenly stop calling without a reason, so I figured I’d say a few things.

I don’t think we’re a good match and after looking at us on Cupid again, neither does Cupid. We’re a 35% match on ethics questions and 52% on lifestyle questions. And I think the lifestyle issue is the bigger one. I think Cupid’s matching system works best if the user answers more questions. I noticed you only answered 92 questions—so I’d recommend answering more. Cupid was founded by Harvard math majors, so I have confidence in their match algorithm.

I feel like I’m adaptable to almost any situation and get along with all kinds of people. You have told me multiple times that there are people you flat out don’t think you have anything in common with nor want to talk to—like the people at my friend’s party. I can’t date someone who doesn’t feel comfortable navigating through and thriving in the diverse social environments that I always find myself in. I feel like especially in a city like New York EVERYONE has something in common just by virtue of living in the biggest city in the US. Also most people aren’t from here, so that’s always something to talk about. My profile says it all when I talk about the various music and situations that I love. I also love crowds.

I also seem to have a lot more energy than you. I think I work longer hours, party much more, go out more, sleep less and probably exercise more than you. Plus I’m older. I love spending time relaxing on the couch, but I also love to dance every week. It would be ideal to find a partner to share these things with.

Lastly, on our first date you told me that I talk a lot but that you didn’t feel like I talked enough about the “real me.” You asked me if I ever open up to girls on dates. On our third date I told you all about my parents and I feel like instead of just listening to me and/or trying to see things from a different perspective, you basically just told me what “I should be doing” and essentially what I was doing was “wrong.” As in I should be calling my mom every day and not speaking poorly of my father. How are you going to ask someone to open up and then chastise them for doing so? I didn’t think that was very cool at all.

I highly recommend that you move to San Francisco once you are done with New York. It’s got a large tech culture which is great for design. The cafe culture in SF is much more European style than New York—thus there are more cafes and more people working from cafes. I think SF may be better suited for your pace of life.

Montauk is the place that I recommended that you take your father. I know you mentioned that he likes to take the train, but I highly recommend not taking the train there if not spending a lot of money is important to you. Montauk is pretty rural and small town (but spread out) thus there is not much public transportation. Taxis there are very expensive and not very convenient if you want to go to more than 1 beach or location. It’s not very walkable from the train station. Thus I recommend driving. The drive out there is beautiful. I took a date there last year and she loved it. I would definitely bring a change of clothes. It’s super casual during the day (surf/beach attire) and it gets fancy at night at the restaurants and bars.

I wish you the best in your dating and other pursuits and it’s a small world, so I imagine I’ll run into you again somewhere on this planet.



Now for the discussion. My ass started twitching somewhere around paragraph four. This guy sounds like a pompous, self-centered gasbag. It made me wonder why a girl would tolerate actually getting to date three with him. It’s my belief (and practice) that you go out with a guy twice, and if you aren’t in to it, or it doesn’t click for you, you move on. Why linger?

In that respect, I do appreciate that this guy had the sense to realize he and Miss Lonelyhearts weren’t making a love match. I’m also big on closure, so I’m proud of him for giving that to her. Letting something fade away is one of the most obnoxious things that men do. They hate confrontation and they hate tears and so, given the opportunity, will avoid, avoid avoid.

The problem here is that these two clowns (they both kind of sound like dicks, to be honest) didn’t actually know one another at all. Three dates does not a relationship make.  Thus, sending an email this intense is a lot weird.

Would I want to get an email like this? Hell no! I don’t want some dude I don’t even know kindly ‘informing’ me about my flaws. I do look in the mirror, I know what mistakes I make, thanks. I don’t care how we’re not compatible. A nice, ‘I know that you can sense this isn’t the best match ever, let’s be friends’ (even if you don’t mean it) would suffice.

Also, this guy totally takes the OKCupid algorithm to heart. Compatibility is important in a lasting relationship, but it doesn’t always have to be a deal breaker: opposites do sometimes attract.

I will say this: OKCupid is an awesome dating site. The creators encourage you to answer as many personal questions as possible so that you can, in fact, see if a person you’re interested in physically will be a match in terms of lifestyle and values. For example, one guy (who shall remain nameless) answered that he wouldn’t need to have sex before marriage if he was really into a girl. You’re probably saying to yourself, “Well, that’s sweet. This LoveTrekker girl is heartless!” But before you start throwing your bunched up panties at me, hear me out. First off, I’m about 99.9% sure the guy was lying to sound sweeter than he really was. Secondly, sexual chemistry is an important part of a relationship. It isn’t as large as love or trust, but it’s up there. Can you imagine coming home to your husband/boyfriend/fiance and being so physically estranged that you’d liken it to taking one for England? Sex shouldn’t be a duty.

In conclusion, never a) send this kind of email to someone you don’t really know b) Certain OKCupid users can be a bit aggressive c) If something isn’t working, don’t drag it out — it isn’t fair to either of you and d) never, ever date a guy that says ‘ciao’, unless he happens to be from Italy.

Love to love ya


You can follow any responses to this entry through the RSS 2.0 feed. You can leave a response, or trackback from your own site.
3 Responses
  1. [...] they chat via an instant messaging service, then move on to a Skye-like video system and finally, if they’re both still into it, [...]

  2. Mrs Smart says:

    very nice post, i certainly love this website, keep on it

  3. Seduce your man…

    [...]» Blog Archive » The Worst (Or Best) Kiss Off Email Of All Time[...]…

Leave a Reply

XHTML: You can use these tags: <a href="" title=""> <abbr title=""> <acronym title=""> <b> <blockquote cite=""> <cite> <code> <del datetime=""> <em> <i> <q cite=""> <strike> <strong>