Dear Wendy
Dear Wendy

From the Mailbag: “My Boyfriend Wants a Sex Change!”

Every once in a while, I get letters that are obviously fake (besides the content of the letters, other clues include the email address of the sender, their sign-off name, and the photo attached to gmail account). I don’t usually post them, because why use the space and energy for someone who doesn’t actually need the advice, but I figured we could use a little levity around here this week, so enjoy this gem:

I am so confused I dont know what to do, the other day when I went round to my boy friends, he came out to greet me wearing a dress, sorry, when I say wearing a dress, I mean dressed completely as a woman, you know dress, tights, and high heels, I just stood there in shock, just looking at him, I mean he even had a false bust, when I caught my breath I asled him why he was dressed this way, he explained that he didnt want me to see him dressed like this just yet, not until decisions hed been made, when I asked what he meant by decisions he explained that he hade been secretly dressing as a woman for many years, and he couldnt stand the agony any more, he had made an appointment with a doctor to ask for a sex change, he then asked me If i would drive him to the appointment, I guess I was still in shock, or wanted to protect him as I agreed to do this, so after he put on a wig and a pair of high heels we set off, on the way to the doctors he asked me to stop calling him by the name I know him as ( Steve) and start calling him Sarah instead, thisI have done not only to make him happy, but he has had a deed poll to make this legal, I really love my boy friend, and being bi sexual, I know I can love him as a woman, its just that this came as a complete shock to me I had no Idea, yes he does look cute as a girl, but I feel decieved, I dont know what to do for the best, please help ,please respond by emai, as Sarah (steve) doesnt know Im writing this. yours confused, Lisa

The return email address on this letter was a man’s name, and the photo was that of an older gentleman, by the way.

20 comments… add one
  • artsygirl July 25, 2012, 1:45 pm

    Maybe the older gentleman was really Steve/Sarah and he was projecting. 😉

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  • Tax Geek July 25, 2012, 1:52 pm

    Wasn’t there an actual letter (maybe a year or so ago) that was about SO wanting a sex change operation?

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  • Katie July 25, 2012, 1:58 pm

    Oh! Maybe he is Steve/Sarah and this is his grand plan to tell his girlfriend he wants a sex change and he is feeling out whether this would be a good tactic.

    It would not be a good tactic, just as an FYI.

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  • MissDre July 25, 2012, 2:01 pm

    Wow, this letter was just one really long run-on sentence. Has this person never heard of punctuation?

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    • iwannatalktosampson July 25, 2012, 2:12 pm

      MissDre! How ya been? How is everything going with the boyfriends family?

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      • MissDre July 25, 2012, 2:39 pm

        I think they are doing fairly well considering the circumstances. Just keeping quiet and low-key.

  • Caris July 25, 2012, 2:04 pm


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  • Fabelle July 25, 2012, 2:50 pm

    Oh god, that hurt to read. All the fucking commas.

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  • fast eddie July 25, 2012, 1:54 pm

    That’s funny except for the spelling errors, but in truth the sender is so lonely that he had to make that up, or a very bored teenager screaming for attention. (snicker)

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  • McLovin July 25, 2012, 3:36 pm

    Clearly, your, love, for, both, Steve, and, Sarah, is, a, special, bond, that, can, never, be, broken, Please, keep, us, updated, and, remember, that, communication, is, the, key, to, every, healthy, relationship,

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    • FireStar July 25, 2012, 3:42 pm

      That made me laugh out loud!

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      • iwannatalktosampson July 25, 2012, 3:48 pm

        I’m embarrassed that I didn’t have any trouble reading it. I spend too much time with 14 year old girls. 🙁

    • Eljay July 25, 2012, 5:32 pm

      OMG, I just laughed so hard I snorted! LOL!!!

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  • ktfran July 25, 2012, 4:06 pm

    True story.

    My close friend’s cousin was married to a dude. Everyone, except the cousin, thought the dude acted a little on the feminine side. Cousin was ok with it. Until dude decided he was gay and wanted a divorce. Ok, she has sad, but got over it. A while later cousin got a call from a friend and asked if she was watching MTV’s True Life. Apparently, dude decided he wanted a sex change, went on the show, got one and now goes by Elle. Dude didn’t warn cousin (the ex), but her wedding photo was on the show. She was blurred out, of course. Still, that has to suck.

    And I’m honestly not making this up. It does happen! But this letter cracked me up.

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    • Kelly July 25, 2012, 4:14 pm

      Wow, I’ve seen that true life! It was sad when Elle’s mother died.

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      • ktfran July 25, 2012, 4:20 pm

        It is sad.

        Now, my friend’s cousin is dating someone new and the jury is still out.

    • kerrycontrary July 25, 2012, 5:03 pm

      I’ve seen that true life as well. Crazy! My sister told me about this guy who got chemo, and it changed his hormones (this really can happen), and all of a sudden he was gay, and then he decided he was transgender and got a sex change. Normally I don’t think people ‘decide’ they are gay or “decide” they are transgender, I just didn’t have better vocab to use in this story.

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  • Eljay July 25, 2012, 5:35 pm

    I just got a headache.

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  • bittergaymark July 25, 2012, 9:05 pm

    Well, before he gets “it” lopped off — she should be sure to get knocked up because — (like seemingly every other LW lately!) — this sure sounds like a super-duper ideal situation to bring an unsuspecting baby into…


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  • Elizabeth July 26, 2012, 8:20 pm

    For anyone interested in this subject and looking for a great read about it – She’s Not There by Jennifer Finney Boylan is FANTASTIC.

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