Matt Kailey

This week’s Ask Matt involves a reader who has fallen in love with a close lesbian friend who has come out as trans. And yesterday, I gave the easy answer: tell the guy how you feel.

But before you do, there are some questions that you really need to explore with yourself. I offer these questions not to be critical or to discourage you, but because they are important for you to consider – for your own sake and for his.

1. Did you have any romantic attraction at all to this person before he came out to you and told you that he was transitioning from female to male? You say that his revelation about being trans was sexy and brave. Was it this revelation that sparked the romantic feelings?

Although many trans people disagree with me, I have absolutely no problem with “transness” being a characteristic on someone’s “Perfect Partner” list. I think that many of us are different from non-trans people and that we have insights and things to offer that only a person with our experience has.

However, the person that you are now in love with is the same person that you have been friends with for several years. If you felt nothing but friendship until this revelation, you need to ask yourself why not – and why now? And you need to make sure that you’re not glamorizing or romanticizing the trans experience or trans people in general.

We are, most of the time, very unglamorous – we have bills, we have to go to work, we get tired, we get sick, we snore, we poop, we sweat, we look really crappy in the morning, we get really crabby when we’re stressed … just like everyone else.

That said, even if this revelation was the catalyst for your feelings, that is not necessarily wrong or bad. A long-term friendship turning into love is not always a gradual process. In fact, frequently something will happen that “wakes you up.”

You suddenly start to see the person in a different light – kind of like “Wow. Who are you? I didn’t realize you were so cute/sexy/smart/funny/nice/hot.” It happens all the time. So don’t dismiss it as a mistake. But exploring your feelings to identify where and how they originated will help you out in the long run – especially if he asks.

2. Can you handle physical and emotional changes in your partner? I don’t know your sexual orientation, but if you are a lesbian and you are attracted by “female” attributes, such as breasts, you really need to think about what it will mean when they go away, if they go away.

If you are straight and you are attracted by certain “male” attributes, such as a penis, body hair, or facial hair, you need to think about what it will mean to you if these attributes do not materialize. A penis can be strapped on, but body and facial hair, a low voice, and male pattern baldness are things that are less predictable and depend on how the hormones interact with genetics.

Also, although a person’s basic personality is likely not to change, there are many qualities about that person that could change. This is true of any person, trans or not, over time, but it’s just something to be aware of. If you have a picture in your mind of what this person will be like after transition, are you able to get rid of it and live with ambiguity for a while? Are you able to stand back and resist trying to shape him into the person you want him to be?

3. Are you able to take a back seat to transition when necessary? In many new relationships, the new partner is the center of attention. Other plans get canceled, work gets put off, and friends get put on the back burner so that the new lovers can spend time with each other.

But transition can be a time-consuming, self-absorbing process, and there will be things competing for his attention, like therapy and medical appointments, support groups, and new trans friends. And sometimes, he may just need time alone to process what’s happening.

I’ve seen established relationships go south because of this. It will be particularly difficult on a new relationship, so make sure that you are prepared to handle this. How will you feel when he can’t see you? How will you feel if he just wants to be alone for a while?

4. Can you handle being seen and treated by the world as a lesbian couple for a while and then as a straight couple long term? How closely linked is your own sexual identity to how the world sees you and how others respond to you?

5. How prepared are you for him to be out as trans – for your friends, family, coworkers, and others to know? How prepared are you for him to not be out as trans – for it to be a private matter that is not discussed with any others, ever?

6. Since you have known him for quite some time as a lesbian, are you going to be able to see him as a man? Are you going to be able to let go of old habits and interaction patterns? Are you going to be able to refrain from tripping down memory lane if he doesn’t want you to? You are still using the female pronoun to refer to him, as a reader yesterday pointed out, but my guess is that he is probably still using it in public as well. Are you going to be able to make the switch?

This could be a concern of his, since your friendship has been that of two females – at least in your mind, if not in his. If you enter into a romantic relationship, the whole dynamic will change anyway, but you will still have memories of your previous life as friends. How easy will it be to let this go if necessary?

There are no guarantees in any relationship. People change, people cheat, people fall out of love, people just grow apart. But entering into a relationship with a person who is just beginning transition does have an extra layer of “stuff” attached. However, if two people really care about each other and are committed to making things work, you can’t ask for much more than that in any relationship.

So, based on that uncharacteristic lapse into sentiment, I return to my simple answer of yesterday, which is “Go for it.”

Readers, what other things should she consider?