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Good friend is secretly transgender (general adivce would be nice)

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So fairly recently I found out that one of my best friends is actually transgender (by snooping). He's still closeted even in terms of sleeping with men even to me so I don't know how to approach this conversation. I knew before this that he had been "dressing up" and having his hookups call him Jennifer. So at the time, figuring it was just dressing up, I passed on some hints that it was his fetish and he should keep it to himself. Now that I know he's planning on transitioning I feel like I may have accidentally told him/her that I don't want to know her afterwards. I feel kind of like a dick now and was hoping that other folks would know some ways of talking about something like this. I feel like I need a more experienced perspective since I haven't openly dealt with transgender people before.
 
Why would you want to ditch your best friend once he becomes a transgender...living his/her truth...finding his/her happiness? Will the female version of him endanger your life? I would think as his best friend (yourself) would be there to support him throughout the transition. No?

Keeping it a secret is a long struggle (years) within himself already. I am sure he does not take his commitment to go through a gender transformation lightly.
 
Be honest. Apologize. Explain that your views have changed. Tell your friend you are willing to change pronouns when you are asked to do so.
 
I would approach it with compassion. Approach it as a reporter...ask questions to be enlightened in the subject. Understand his struggles...on how he knew he wanted to change his gender. It takes money to commit to therapy and meds for the transition. This is the time he needs support from his friends and family the most.

Good luck!
 
I have a friend that is transgendered. It was a brave thing she did to admit things to herself and go through the process. She was an awsome person before and is still an awsome person now. I do slip on the name and gender referance occassionally but those slip-ups are becoming fewer and fewer. As I said, she's an awsome person and I'm proud of her.
 
Now that I know he's planning on transitioning I feel like I may have accidentally told him/her that I don't want to know her afterwards. I feel kind of like a dick now and was hoping that other folks would know some ways of talking about something like this. I feel like I need a more experienced perspective since I haven't openly dealt with transgender people before.

The question you have to ask yourself is whether you are in this for the long haul. If you cannot or will not stick with your friend through this, then it would better for you both that you don't add more insult to injury and just move on.

If you are willing to make the commitment to trying to understand and accept, then it's quite simple- you shut up and listen. This did not happen with your friend overnight- it's something that has been going on for a while and is something your friend has been hiding from you (and everyone else) for some time. Don't BS and say that you understand if you don't feel that way. Be real- there's nothing to be lost by being honest that you don't understand and that it's tough for you to feel like you're losing the friend that you know as a man. Make it clear that you're trying to understand and that you want to be a friend
 
So fairly recently I found out that one of my best friends is actually transgender (by snooping). He's still closeted even in terms of sleeping with men even to me so I don't know how to approach this conversation. I knew before this that he had been "dressing up" and having his hookups call him Jennifer. So at the time, figuring it was just dressing up, I passed on some hints that it was his fetish and he should keep it to himself. Now that I know he's planning on transitioning I feel like I may have accidentally told him/her that I don't want to know her afterwards. I feel kind of like a dick now and was hoping that other folks would know some ways of talking about something like this. I feel like I need a more experienced perspective since I haven't openly dealt with transgender people before.

Well I went through a phase like this recently, ME being the transgender person. Right now I identify as a "gay man with transgender tendencies" (whatever that means) just cuz I don't feel the need to transition and I feel 95% comfortable with how I look and live right now. This is such a personal subject that I would advise you to try and casually come up with the subject (without talking about your friend per se) and letting her know that you're completely fine with the subject and that you would be supportive. Hopefully it'll help her open up when she feels ready.
 
Yeah, I don't care that she's TG, and I wasn't looking to ditch her, andsince she hasn't come out, opening that line of questioning would be admitting that I snooped. That and the escalation from what I thought was just a fetish to actual trans means that it became something I don't know how to deal with. I'll be there for her no matter what, you don't throw away 15 years of friendship just because they aren't the gender they were born as. It's just going to be difficult to maneuver conversation wise.
 
Recently Time Magazine spotlighted Transgender (an actress) on the cover of the magazine. It was groundbreaking and was all over the news media. It was a water cooler conversation in the office because NetFlix's "Orange Is the New Black" is a hit series. You can read more here. This actress is playing a transgender (male to female character) in the series. What is more interesting is the actress has a twin brother in real life that is not transgender. The brother is in the series playing the transgender character (male) before the gender transformation.

You could use pop culture as a reference in your conversation with your friend.
 
Tell him (I'm using him because currently that's how he presents himself to you) that since transgender issues have been getting attention you've been thinking about your initial comments to him and you've changed your opinion. Explain that you're a supportive friend and always will be. Ask if it's time to use Jennifer and she.
 
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