When Your Guy Friend Becomes Your Girl Friend

I consider myself an open-minded person, someone who is pretty well versed in the myriad definitions of gender, and do my best to be non-judgmental. No amount of theory, however, truly prepares you for the first time a person you have known your whole life as a man tells you they will now be living their life as a woman.

I have found that over the past year or so, it has grown increasingly more difficult to shock me. I attribute a substantial amount of this desensitization to listening to and reading Dan Savage. Once you’ve learned how to successfully indulge a cream pie fetish, most things people consider “kinky” become almost mundane. Advice is doled out to people from all walks of life, whether it is a straight, monogamous husband in New York, a queer 19-year-old college girl from a small town in Nebraska, a transgendered woman in Texas, it seems almost everyone can find themselves represented at some point. Because of the Savage Love, as well as the circle of blogs and tumblrs I frequent, I have gained a large amount of insight into worlds of others and been forced to recognize my overwhelming privilege time and time again. I like to think this makes me more sensitive to the needs of others, and while I definitely still struggle with some things – ableist language being the one I am focusing on now, so please keep me in check if I slip- I hope that I can be an ally to other groups struggles. All that being said, when my friend Jeff* sent out a group text the other day titled “Goodbye (you won’t want to know me)” and went on to link to his blog for further information regarding his decision to live his life as a woman named Jenny going forward, I was taken aback.

For the sake of clarity here, I will be using male pronouns when discussing events leading up to the first text message, then the female for everything following.

I have known Jeff for most of my life. He is a friend of my older brother’s from high school, so he has pretty much always been around. He had substance abuse problem throughout his 20s and 30s and has had a hard life. He has lived a mostly transient lifestyle for the last 15 years, hopping around from place to place, even living in a tent in the woods behind my brother’s house for awhile. He was a jack of all trades, working odd jobs all the time to have enough money to get by. He has done a ton of work at my parents’ house, from moving furniture to building play structures. He helped me move into my house and helped lay pavers in my backyard. While he is not a big guy, quite the opposite, he did the work of someone twice his size without fail. He was a tradesman and took great pride in his workmanship. He would take any job that came his way, do it to the best of his ability, and take pride in it. When he helped out at my family’s store last year, I would give him a ride to wherever he needed to go at the end of the day. I would pay him at the end of the day, and without fail, he would want to be driven somewhere to get food, not for himself, but for his homeless friends who didn’t have enough money to eat. He was barely scraping by with enough money to have a place to sleep, but used every spare dollar he had to take care of others. It was, and is, one of the truest testaments to his character that I can describe.

When I say I was taken aback by his revelation, I don’t mean that in a negative way; I just mean it came as a total surprise. I never, not once, suspected anything. That realization made my heart ache, knowing that a person I have great affection for had been hiding this integral part of themselves for as long as I had known them, living half a life in shadows and not being free. The text itself made it clear that he assumed nobody on the distribution list would want to be around him as a her, but that this was what needed to be done and so he was saying goodbye. Heart. Breaking. I responded that I fully supported the decision, thought that it was incredibly brave, and that I was here if needed. Her response? “Thank you. I just wish others were like you.” Arrow. Through. Broken. Heart. What do you say to that? The only advice I had to give was that the good people in her life would come around eventually, and the others could go fuck themselves.

I’m not sure where to go from here. While I definitely consider Jenny a friend, it’s not as if we hang out and go to the movies. I don’t want to overstep my bounds, but I want to help where I can. She has sent and posted a few pictures, and not to be insensitive, she needs help in the make-up and clothing department. How does one go about approaching this? She texted me yesterday saying she would love to get a manicure sometime, “if I would be comfortable being around her.” I reiterated my support and that she didn’t need to waste anymore time worrying about that with me, and made plans to go with her next week. I’m hoping others here may have some guidance for me on what is appropriate to offer, hoping some may have more experience on what is totally new ground for me. We are close to the same size- is it okay to offer clothes? Is it offensive to offer hair/make-up tips? I want to be supportive and helpful for what is a MAJOR life change for her, but I don’t want to be insensitive or hurtful unintentionally. While I admit that I enjoy all the fun and girly trappings and all that goes along with that, I also am concerned about her safety. As I mentioned, she previously led a nomadic sort of existence, which is unsafe for both men and women, but even more so for women, particularly one who isn’t quite “passing” yet. Any advice would be a gigantic help, my little Persephoneers, as well as letting me know if any of the above was not okay. Here’s to hoping I can keep my foot out of my mouth by having my heart in the right place.


*names have been changed

15 replies on “When Your Guy Friend Becomes Your Girl Friend”

i think you should give yourself time to become comfortable with jenny. you are trying hard to be open-minded and supportive, and that will come more naturally as you get to know your friend better. yes, you’ve known jeff your whole life, and jeff is still there, but you are just learning about jenny. it would feel just as strange to give this kind of advice to a new neighbor or co-worker. but when you feel comfortable with a girlfriend, it just flows.

I don’t have any personal experience of this, but I want to wish the best of luck to Jenny, and whatever worries you have about being supportive enough, the fact that you’re compassionate and aware enough to consider this so closely is a really good thing.

Another resource (for you and/or Jenny) is Julia’s blog on the Guardian about her transition process. Some of it may not be relevant because it’s based on the NHS process in the UK, but as a cis person who doesn’t have any trans friends or acquaintances (that I know of, of course) I found it educational and helpful.

I have two thoughts, one – do your best to treat her like you would any other girlfriend and don’t second-guess yourself too much. Watching someone else try to figure out how to act around you makes everyone feel awkward. And two – I am always in favor of going straight to the source. If you are worried about offending her, tell her that you’re afraid you’ll say something stupid and she should just let you know if you do.

As for the makeup thing, I would either ask outright, “Can I do your makeup sometime? I think (X) would look great on you,” or if you would rather be more subtle, see how the manicure thing goes and suggest a second outing to play at the cosmetics counters at the mall. Then you can offer some tips under the guise of window shopping.

The fact she wants to get manicures is a sign she may be open to your help when it comes to makeup and clothes. I agree with SaraB that asking outright is probably the best way to go. It seems like while you’re out getting your nails done, it’d be the perfect time to bring it up, while you’re already doing something beauty-related.

Thank you so much for your advice and my apologies for the delayed response! We hung out last night and did manis and pedis, and it was awesome. She was really open to suggestions and advice, and many of my fears for her safety were laid to rest. We are setting up a make-up lesson soon!

I’ll point my girlfriend at this post when she wakes up, see if she has anything to add, but in my experience, do what you’d do with any woman friend. Maybe even what you’d have done with a girl friend as a teen. Play dress-up out of your closet, so she can get an idea of styles that might work. Go on shopping trips where you try everything on and buy nothing. Go get makeovers at makeup counters. (If, in fact, you’d do these things with other women friends. If not, it may not be such a great idea. You won’t be as comfortable, and Jenny may interpret that as discomfort with her.)

Don’t forget to take Jenny’s style preferences into account, too. Not all transwomen like the same style — my sweetie dresses geek for casual and goth/industrial for clubbing; another friend of ours dresses old-school hippy all the time — and her preferences may not match yours. Let her find styles things she likes, and help her find specific garments that fit her well. Remember, though, that if she’s going on or has recently started HRT, her body’s going to be changing shape, possibly quite rapidly. It’s smart not to buy a whole lot of clothes right at the beginning.

And I second someone else’s suggestion: You might help her look for a trans-inclusive community center or something. (Also, yes, very definitely work hard on getting pronouns and names right.)

Thank you so much for this advice, and I apologize for my delayed response. We hung out last night and had a great time, and had really open discussions about everything, which was awesome. I told her to let me know if I ever overstepped my bounds or made her uncomfortable, and she let me know that I was doing fine, so I was relieved. I gave her one of my wigs, and she text me later that night letting me know that all her friends thought it was perfect, so that was a great feeling. Thanks again!

There is some debate over that. Some say that gender is not a verb, and that therefor it’s transgender; others say that transgender gets used as a noun too often, and that using transgendered helps to remind people that it’s an adjective, and applied to a person: transgendered woman, e.g.

(If I understand the debate correctly, which I might not.)

I have been friends with three trans people in my life. Unfortunately for you, I’ve only been friends with trans men, but here are a couple of pointers I can offer:

-Change Jeff to Jenny in your phone book. My friend switched from Hiedi* to Ryan* (*not real names) and he asked me to do this, and so I did, right in front of him. It meant a big deal to him, and I’m sure your friend would appreciate it.

-It shouldn’t be, but the pronoun switch is difficult. The best thing to do is to correct everyone who ever makes the mistake, not only for them, but also to remind yourself. I hope to be to a place where I don’t have to think about it, but I’m not there yet.

-When Ryan looks especially masculine, be it a new binder or a new set of clothing, I tell him, and he just lights up. Your friend is a woman, and when she is looking especially womanly, compliment her. I don’t think it’s out of line to offer makeup or hair advice — obviously step off if she demurs or doesn’t seem interested, but you don’t learn thirty years of hygiene and beauty tips over night.

-The safety issue women face is a real concern. If you feel comfortable, I would let Jenny know that your place is always available instead of spending the night outside, or point her to some LGBTQ outreach centers that could help if she ever finds herself in that position again. The threats that women, especially trans women, face in public is not imaginary.

The last bit here about offering a safe place – and possibly even some friendly advice about the cautions women have to take to ensure their safety in public – are a really good point. Men don’t grow up being socialized that way; women, and transwomen especially, face a much larger threat of violence and harassment.

I’m glad you were able to be there for your friend. She sounds like a courageous person who deserves all the support in the world.

Thank you so much for this, and please accept my apologies for the late reply. We hung out last night, and I did slip up twice on my pronoun/name usage, but she was exceptionally gracious about it. The compliment advice is really good, I hadn’t thought about that, but it is so true. I was able to get a few in, and she really enjoyed getting her first pedicure so I let her know how pretty her toes were. We also talked at some length about my safety concerns for her, and she put many of my fears to rest. She said she may be a girl now, but she can still kick someone’s ass in heels if necessary!

I think being a source of support will mean a lot to her. I don’t think you need to worry about offending with hair and makeup tips, I’m sure she would appreciate some feedback. I still appreciate feedback, and I’ve been wearing makeup for 14 years! There is a column on McSweeney’s that I’ve been reading for a while which is a funny (and sometimes heartbreaking) journey of one woman’s journey through transitioning. Give it a read, I think it might help with some insight:

This link is great, and I have forwarded it on. It is nice to see the topic addressed in a way that infuses witty commentary and lightheartedness, along with an open and honest portrayal. Thank you so much for your advice and help. We hung out last night and had a blast!

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