But what if he replies yes

Then the guy should have no problem if OP used to be a guy

No, you reply "Didn't you also?"

Because that's a) a really personal question to ask and b) when asking super personal questions, it's generally polite to ask in person. Not through a supremely blunt text message.

I agree. Personally, I think if that person is comfortable with you it is okay to ask such a thing, but face-to-face, and in a more polite manner. He could have gone about it a million better ways.

Um... Yeaaahhh.... you're assuming all transgender women have dicks... That's not true. Not even by a long shot.

But when you're dating someone questions like that aren't really that weird?

I would assume they are not dating. If so, op would probably refer to him as their boyfriend.

You dumbass if shes in love with a guy then im 100% sure he was born a guy

Haha logic

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#29 that doesnt even make sense. it says shes been in love with him for 3 years or something i think. these two people are obviously not 3 years old so she wouldnt know. and i doubt shes a crazy stalker?

WTF? Are you stupid?

Lol. 19 must be a tumblr user. Hey 19, you said "that MAN". How do you know the person OP was texting identifies as a man, huh? /sarcasm

How? He was only asking something. Yes, the way he asked it was blunt and impolite, and overall a bad way to ask something personal like that. But that doesn't mean he's transphobic.

If you ever think that someone is transgender, whether you are right or wrong, you never ever ask them "did you use to be a man/woman?". It is one of the biggest slaps in the face other than being purposely misgendered. Take it from an ACTUAL transperson.

And no I am not on tumblr

#32 Well, let me reply to you then since I'm "an ACTUAL transperson" myself. Yes, it feels like a slap in the face when someone asks that, that still doesn't make someone transphobic. Just misinformed and/or blunt/impolite, like I said earlier.

Maybe he's interested but he's heard something elsewhere. If he knows OP is interested, whether she has a uterus could be important information.

Not to sound dumb but how would you go about getting that information about somebody?

#27 i use tumblr but that doesnt mean i think this is transphobic -_- you obviously havent been on tumblr before to know that not every post has to do with current events

You aren't very bright 27. If the person OP was infatuated with didn't identify as male, he wouldn't have asked the question he did because he would have known it would be hurtful either way. Simple logic to determine that the person in question identifies with their assigned gender if they ask a question that is as invalidating as the one he did. One would presume you have a brain, so maybe you should use it for more than taking up the space in your skull. It might stop you from making an ass out of yourself.

thats bullshit wtf is the slap in the face? your trans, you know its not exactly natural, so just embrace that shit and dont get your panties knotted when someone is curious or even confused about your appearance.

OP wrote it correctly.

A more appropriate way of asking would be "Are you transgender?" or even "Were you assigned male at birth?"

There isn't an "appropriate" way to ask that. It is rude and callous no matter how it is phrased. It not only is a rude to ask about what genitals a person has or has had, the question both implies that people of a gender "have to" look a certain way, but if the person WERE MtF, he would be saying that he doesn't "read" her as a female. He would also be invalidating her gender identity by saying that she 'used to be' a man, when she would have been female even before transitioning. Unless she was genderfluid and had times in a "male" gender state. Even putting all of that aside, it is ridiculous to stop being attracted to a person of the gender(s) you are interested in because they might have different genitals than you might expect- they would be the same person, just with a different set of equipment than you thought they had.