Matt Kailey

A reader writes:  “A close lesbian friend has recently confided in me that she is transgender. I was not put off by this at all. I saw her honesty as brave and sexy! I have fallen in love with her and am unsure how to take that next step. I don’t want to overwhelm her by admitting my feelings while she is preparing for a big change, but the certainty of my feelings makes it difficult to stay silent.”

My interpretation of this letter is that this individual has told you of his intention to transition from female to male. He obviously feels close enough to you to confide in you. I don’t know whether or not you have sensed that the attraction is mutual, but even if you haven’t, that doesn’t mean that it isn’t or couldn’t be.

But there is a lot going on here, so this is going to be a two-part response, and I hope that readers chime in, too.

There is, on the surface, a relatively simple answer: You invite this person out for coffee or lunch (pick an activity and a location that allows for an easy out – that allows one party to say, “I’ve got to get back to work now. I’ll talk to you later.”), and then you have “the talk”:

“I know we’ve been good friends for a long time, but I want you to know that I’m interested in more. I know you’re preparing to go through a very major life change, and I want to be there for you – definitely as a friend, but hopefully as something more. If you’re interested in pursuing that, either now or in the future, I am interested as well. If you need to think about it, that’s fine. If you’re not interested, I hope that we can still remain the close friends that we are now.”

Of course, you’re putting him on the spot, but there’s really no other way to do it. You’re risking rejection, but so is everyone who attempts to initiate a romantic relationship – or to even ask for a dance in a club. You’re risking the friendship, because if he’s not interested, then remaining friends could be too uncomfortable for him. This kind of admission can change the quality of a friendship or ruin it.

But you’re not going to be able to go on for much longer without confessing your feelings, so you have to take the risk. And if it’s all or nothing – if you don’t think you can remain “just friends” – then you need to say this, too, although I would caution you that sometimes the friendship is better than any relationship that you might picture in your head, and it will possibly last longer, so I personally would advise against an ultimatum. It’s not going to make him love you, but it will end the friendship.

You are right about the overwhelming part, because transition can be extremely overwhelming. I have often had guys who are just beginning transition express frustration about not being able to find a relationship, while they are also expressing frustration, anxiety, and fear about a million other issues, including their own identity, their future, and so on.

I usually advise them to do some soul-searching and inner exploration as they are going through the early stages of transition, and to concentrate on themselves – who they are, who they are becoming, and what they want for themselves – before trying to find a new relationship.

Once they are more secure in their own identity and their own life, they will be better equipped to share that self and that life with someone else – and they will be better equipped to know what they want and what they have to offer another person.

That said, most of the guys who have expressed this frustration have not had a potential relationship fall into their lap. And most of them would have probably welcomed this if it had occurred, provided that the attraction was mutual.

So the simple answer is that you need to tell this person how you feel. It’s up to him to decide whether or not the complexity of transition and the complexity of entering into a new relationship at the same time are too much for him. You have decided that you want to take a chance on this relationship. It’s up to him to decide whether or not he does as well.

If you don’t tell him because you’re concerned about him being overwhelmed, then you’re not giving him the chance to make the decision for himself. He’s an adult, and he’s already made one major decision about his life. He’s capable of making others, but he can only make a decision about this situation if he has all the information. And you’re the only one who can give it to him – so go for it.

But I also have a more difficult answer – some things for you to think about before you go for it – and that will come tomorrow in part two.

In the meantime, what do readers say?