I can’t quite recall how it came about but yesterday our tea-room conversation turned briefly to when would be the right time to tell someone you had surgery to change your gender. Is it a good idea to do so when you first start dating? April did this in The IT Crowd, humorously being misheard as saying she “came from Iran” instead of “used to be a man.” Of course that could kill any chance of a relationship quite early. Should you then wait? And how long? Would it be seen as a betrayal of some sort? Would it be worse than saying you used to have a different religion or be a vegetarian? And if it would change how you see a relationship does that mean you’re placing more value on a person’s body, or what their body used to be, than the person inside?
I think they’re interesting questions and it’d be good for me not to be the only one writing here. Perhaps this is a good time for such a discussion.
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Evidence & Reason 
Never heard of “The IT Crowd”. I’ll have to see how the issue is being portrayed in the show, hopefully accurately and not as yet another punchline.
I fully disclose from the first meeting. It might be revealing private information others do not have a right to know, but I think it’ll prevent me from having any problems in the future. You’re definitely not the only one thinking about the issue of disclosure. I wrote a post about it, if you’re interested. http://transgenderless.com/2013/04/18/dating-while-trans/
@tiffany267: It is a comedy and really doesn’t try to seriously address it or any issues related to it. That said I have seen a comedy take a more mature view. I’m thinking of one of the episodes of My Family where one of the main characters, Ben, reunites with an old friend to find he’s now a female. There Ben shows a lot of growth and comes to accept his friend’s choices.
@transgenderless: Do you think perhaps that might also drive away people that might’ve accepted that after getting to know you? On a point in your blog post, I’m not all that sure I would call not telling someone misleading them. I do think it’s important and should probably come up at some point but on the other hand why tell someone about something that you used to be. It might be rare but not telling isn’t hiding it, they just assumed you were always the same. Perhaps generally a safe bet but not a given. Then again I’m not really that familiar with the situation so I could be totally wrong.
I guess one answer would be to tell them as soon as you could but maybe that’s not tactful. I cant imagine what it would be like. This issue cuts to the heart of just what is a man/woman and what do we accept as one or the other.
This and other issues of the transgendered never occurred to me until I started writing a novel with a transgendered main character. I realized some of the problems that inhere, such as when to tell someone, what bathroom do you use while transitioning, legal considerations involving definitions of gender and what is/isn’t a gay marriage in this context, countless others.