text: my ex is a transsexual? i've known my ex-boyfriend for about eight years. he recently contacted me after several years because he wanted to (out of the blue) confess to me he's a transexual. i've been really excepting of him thus far untill he's recently asked me to start calling him amy and has been leaving not so suttle hints that he wants to get back together.   thats really the last thing i want. he's got really low self esteem and my oppinion of him is his world. i've become extremely uncomfortable with the situation and i'd rather not speak with him at all. i feel like he's using me for therapy and i dont know how to say so without hurting his feelings wow.  ok, for starters, she has put you in a very difficult situation.  leaving aside her request to get back together, just her confession of being transexual is enough to throw you for a loop.  i know.  or, at least i think i know.  i start therapy next week for my gender dysphoria issues.  i forsee many of these conversations in my future as well.  i see where she is coming from to a certain degree, even if i do not agree with how she has handled it with you.  (please bear with me if i refer to your ex with feminine pronouns, for if she is truly transexual, this is how she sees herself.)  she is terrified, litteraly drowning in a sea of turbulent emotions.  so she has latched on to what she feels is her best chance for survival.  you.  you don't give any background regarding the dynamics of your relationship, and lord knows i am not a psychologist, but i would guess that when the two of you were together, you were the strong one, the decision maker.  and if that is true, then she is looking for you to be that person again in her time of need.  that is unfair.  this is her battle.  offer whatever support you feel comfortable offering, but also set out clear guidelines regarding what you will and will not do.  you may hurt her feelings, and that's too bad.  but if she thinks she can go through this transition without any hurt feelings, then she is incredibly niave, and hurting her feelings may just be a blessing in disguise.  just remember, you can hurt somebody's feelings reluctantly or you can do it cruelly.  it sounds to me like you would prefer the former, so be firm, but gentle.  if she is serious about this, then it is time for her to put on her big girl panties and get to work.  i would not give her chances for survival as a woman much hope if she is not willing to do some very hard work, accept a bunch of disappointment, and deal with quite a bit of rejection.  if her desire is strong enough, she will make it.  i will be pulling for her (and for you too)  good luck to the both of you.