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Dear Captain Awkward,

So I met a girl last night, one I’ve run into occasionally when the orbits of our respective circles come into gravitational alignment. We spent the time chatting together and exchanged numbers afterwards. I have zero experience with romantic relationships, but what little knowledge I’ve accumulated from rom-coms and trashy novels leads me to believe we mayhavekindofactually been flirting. She’s smart and funny and similarly awkward, and I felt like we connected really well in the short time we had. It’s early stages yet though and I’m in this weird excited for possibilities but desperately trying to play it cool space.

The thing is, I’ve never considered it possible for me to be in a relationship with someone so I’ve never tried. Ever. I’m trans but lodged squarely in the back of the closet (assigned and currently perceived as a guy, wholeheartedly wishing otherwise as a girl). I can’t imagine myself going through with transition though because I have extremely negative self-image, and the first person to laugh at me would crush what remains of my misbegotten soul.

Thus far my motto has been that if I can’t even love myself, how could I begin to love someone else? That way lies jealousy, resentment, and a whole host of Bad Feelings. I couldn’t do that to anyone because I know that I would do that, eventually. Not the best basis for a healthy relationship.

I don’t even know why I’m suddenly considering the possibility, but something about it strikes me as very selfish. Like, doesn’t my not being upfront about being trans constitute deception? I know I’m on shaky ground here because there are a whole bunch of nasty transphobic deception narratives that trans women have to contend with every day and so I shouldn’t propagate or internalise those. But I’m approaching it from the other side; in my nail-studded closet I’m not being true to myself and I’m lying to everyone else. So… deception, right?

This girl, who is by all accounts an awesome person, who is not obliged to be a receptacle for my obsessive worrying (we haven’t even been on a date, for pete’s sake!), who is totally unaware of all this inner turmoil, doesn’t deserve this kind of baggage. What’s more is that like me she has also struggled with depression and social anxiety. I’m terrified of making things worse for her and fatalistically certain I will. How can I start building a relationship with her while witholding such an important self-defining secret, and even if at some point I became comfortable enough to share it with her, what then? Cisgender people are generally not well-known for reacting positively to such admissions.

I don’t want to assume here but statistically speaking she’s likely to be straight (as opposed to bi, or even more unlikely to be gay). When I interact with her (or anybody else for that matter) I don’t put on a big macho act or anything. I’m more or less honest about who I am and what I like/dislike, just with dampened emotions and responses. A restricted version of me, pushed into the neutral zone between genders. Apparently androgyny is in? I’m not going to cross the boundary into masculinity or male-identification, that’s not me and will never be me. But in an ostensibly heterosexual relationship that burden would typically fall upon me and exert all sorts of pressure to conform. On the other hand I can’t really emphasise my femininity or female-identification because a) I’m too scared to do so regardless; and b) it wouldn’t be what she signed up for.

Can you tell I’m an obsessive worrier? We might date and find we don’t gel after all. She could click her teeth for all I know. But if I put myself out there and something special happens, haven’t I created a moral conundrum hammer that’s bound to smash that special thing into teeny tiny pieces? I also wonder if I’m just in love with the idea of love, or being loved, and wish fulfilment is a shitty way to treat someone. Proximity to Valentine’s Day does not help at all, funnily enough.

I don’t know whether to even attempt a romantic relationship with some careful guidelines in place, or to explicitly make it friends-only, or to NEVER SPEAK TO HER AGAIN!!!!!!111 What should I do?

Sincerely,
Faith, Mope, Love?

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Ahoy Cap’n,

This isn’t a particularly dramatic question, but I’m stumped. I’m a dude who would like to say he’s in his mid-twenties, but probably can’t anymore. For a long time, I would have said I was straight. I was attracted to women, dated them and had relationships with them.  Then, a couple of years ago, I randomly met a guy I knew immediately was going to be a huge deal to me, and I was right: Two years later, we’re getting married, w00t! I’m lucky in that I come from a really liberal, relaxed background, so it was more of a ‘huh, that was unexpected’ situation, rather than a cause for major upheaval.

My question relates to my high school girlfriend, and do I tell her anything (specifically that I’m bi, as opposed to gay, which seems to be what everybody assumes)? On the one hand I think not, because we’re not in touch anymore and I wouldn’t even think to ask this question if I were marrying a woman, but on the other, we were together on and off for almost all of high school, and were each other’s ‘firsts’ in every way that I can think of. I obviously don’t want her back, and I don’t for a second think she wants me, but she/our relationship was really special to me and I still look back on it fondly. I guess what I’m thinking is that I know she’ll find out through the grapevine that I’m with a guy now, if she hasn’t already, and I don’t want her to feel like our relationship wasn’t what she thought it was, if that makes sense? Like, if she’d come out as gay, I think I might be a little sad somehow, because it would mean that we didn’t have what I’d thought we had? I’d wonder if I should have known, and helped/supported her, and I’d doubt myself and the lessons I learned through that love. Also, I’d feel guilty looking back on it happily, because how can you, if you later found out the other person wasn’t as happy as you thought? I feel like I’d want to know, but I also can’t think of a way of telling her that doesn’t come across as horribly narcissistic, basically calling someone up and going ‘hey, getting married to someone else next year, but just FYI, I was totally into you back then’.

FWIW, Fiancé is totally cool with me potentially getting in touch with her, but doesn’t want to express an opinion either way as to what I should do, since he doesn’t know her/our situation.

Thanks!

We get a lot of “should I reach out to this person from my past and tell them something” questions here at Captain Awkward Dot Com Enterprises, and I am trying to develop a working framework on how to tell whether this is actually might be a good idea.

I think the questions to ask are:

  1. Who am I really doing this for?
  2. What do I want to happen after I reach out? I.e. Is this a beginning or an ending?

If this is just a drive-by, where you say your “Hey, I need to tell you something, bye!” and then ride off into the sunset again, then who is this really serving?

If this is about you reconnecting with someone who was very important to you once upon a time, great! As long as you are open to rekindling some kind of ongoing communication or friendship (even a very loose, casual, or even ambient Facebook “friend”ship). Track down her info. Tell her your good news. Introduce her to your dude. Ask about her life. Make plans to hang out for a drink if you are both heading to your hometown for the holidays. Most importantly, assume nothing about how she will react to your news or how it might change the way she saw your relationship. The fact of your upcoming wedding will come up, and you’ll probably have an opportunity to say “Yeah, after high school I figured out I was bi.” If she has the kind of feelings you are imagining, let her be the one to bring them up. But chances are that even if the relationship was an important & positive one, she doesn’t think about you all that much these days and her response will be something like “I did not see that coming. But I’m happy for you!” The goal is coffee, not FEELINGSCOFFEE.

Because I think you’re over-thinking this a lot! When you end a relationship, you don’t have to keep working through issues of how you felt about the person…with that person. One of the reasons that I advocate taking a no-contact break after a breakup, even if you do intend to remain friends, is to give everyone time to get past the need to solve or fix or analyze the problems of a relationship that is no longer happening. There are no clean slates, but there should be a “BYGONES” slate where former partners who are now friends agree not to rehash the past.

So that’s my advice. Seek your old friend for her own sake, for the possible pleasure of her company, or not at all. And if you do, assume nothing about what she feels or needs. She has her own story about what happened between you and the years you spent apart. Let her tell it clean.

I’ll be quick- After getting my teaching degree abroad, I’ve moved back home with my folks because I have no money, and there are no teaching jobs (or really ANY jobs) in my area at the moment. I’m also transgender. I came out to my dad about a year ago while we were travelling together, and he said he wanted me “to be the best version of myself I can” and that we’d work through it together. I haven’t told my mother yet, however… because she and I have a very different relationship, based mostly around her trying to make me more feminine.

So… how do I use my words to tell her who I really am? I’m terrified of her A, making this all about her, B, going all Jesus-y on me, or C, just refusing to accept this, which leads to D, me no longer having a place to live, or parents that love me.

I’m so scared. But I’m stuck, and can’t move on with my life until something gives way.
What can I do?

- I need to get on with my REAL life

Hi Real Life,

Corporal A. Beard here!

Since you have come out to your dad already, it may be helpful to have a talk with him first, to let him know you’re about to come out to your mom. If there are specific things you’d like him to do, like being on-board with modeling the name and/or pronouns that make you most comfortable, trying to calm your mom down if she does get really upset, or even just reiterating the supportive things he told you when you first came out to him, then this is a great time to ask. Also, if being kicked out of your house is a real concern, I’d absolutely bring it up with him before you talk to your mom; hopefully he can be your advocate in this as well if it comes down to it.

Being in the closet feels like trying to stuff yourself into all sorts of ill-fitting clothes that aren’t even the right color.

He was supportive in that initial conversation, which is a positive sign, but sometimes you won’t know how people will react to certain parts of your transition until the moment arrives. Some folks are big on Supportive Talk but have a hard time, you know, actually being supportive in concrete, asked-for ways or dealing with visible changes when they start to happen. I don’t know your dad and certainly hope you don’t get pushback from him, but it’s possible that it will happen, or that you might have to re-explain some of what you told him earlier. Or maybe since then you have talked about this a lot and he has a great understanding of the best way to be supportive, and if that’s the case, fantastic! You have a strong advocate in your home already.

Coming out to someone, especially a family member, is a big deal, and important conversations can be trying in a lot of ways – I often react by completely forgetting what I actually mean to say and fumbling around for the point. If you want to do this in person, it won’t hurt to plan the hell out of this conversation. Maybe even write a script – you don’t need to read off of it while you are standing in front of your mom but it might be helpful to write down something you can practice off of and are familiar with. I think it would also be fine to write a letter you hand her – maybe as you say “here’s something really important I’d like you to read, I’m heading to the park/a movie/a friend’s house and I’ll be back in a few hours to talk more about this with you.”

As to exactly what you tell her, I’d break it into two or three parts:

1: The basic information that you want your mom to know about your identity.

“Mom, I’m transgender, which means [whatever that means to you],” possibly with a side of “this may/may not be a surprise to you, here’s a little detail about how I came to understand this about myself” if you have a quick and easy way to sum that up and want to share it with her. However much or little of your identity as you feel safe telling her, just lay it out in the most basic way possible. Your sense of your mom’s gender-savviness may give you the clues you need to work out the details here. (My own Mean Grandma responded to my coming-out letter with “all I know about transgenderal people is those silly-looking men in dresses I see on daytime tv,” along with some other snide comments, which demonstrated that she had no idea what I had just explained to her.)

2: What you need from her.

I think there can be an extra layer of confusion among people who hear comings-out from others but still wonder “yes, but what do I do about it?” If you can give her concrete changes to make and specific ways to be supportive, this will clarify the issue and give her things to work on. Here is where you ask her for any language change you want (name/pronouns), a break from the femininity-policing, or anything else you need. This is one reason I suggest you ask your dad for these things too, beforehand; having someone at your back who is able to model proper behavior can be a real help.

3: What might change in the future.

If you have plans to change your name, start hormone treatment, make significant changes to your wardrobe, etc. and feel like you’ll want to explore some of that in the near future, especially while you’re still living with your parents, now’s the time to give your mom a brief-as-possible explanation. This may not even be part of the initial coming-out announcement, actually – depending on how things go, you might say “there are more plans and details I want to talk about later, but for now I really want you to know the most basic level” and come back to this another time. If all you know now is that you have a lot of options you’re still mulling over and you don’t have concrete plans to share with your mom right now, that’s ok too.

Overall, I think you want to keep the entire explanation as simple and direct as possible. If you have conflicted feelings about certain labels or are unsure about some steps you may or may not take… now is not the best time to get into the complicated details. There will be time for a more in-depth discussion with your mom in the future, if you feel safe opening up to her more, but I think it will make things easier on everyone if you streamline things to start out with.

The tricky thing is this: you can do your best to plan out how the coming-out process will go, but once you let that information out in the world, there’s really no way to know or control how your mom will react to it. People’s emotions are often unpredictable and messy; she might indeed make it all about her, or about Jesus. A lot of parents worry that they did something wrong when they find out that their children are trans, like they dropped us on our heads or didn’t nurture us in the exact right way. I don’t have any insight into what made me the way I am; if you have a strong belief about it you can certainly share it with her, but whatever reaction she has may just be something she has to stew in for a while before she can really come to accept what you have to say.

She’s entitled to feel whatever feelings come up during this process; to be honest, I roll my eyes at the “I must mourn my son/daughter” idea because hello, I’m right here and not dead at all, but at the same time I realize that it is a process many people go through. I don’t have to like it to understand that it happens. Parents have all sorts of hopes and expectations for their children, and even if you’re approaching this from the angle of being really happy that you’ve sorted out something important about yourself, she might fixate on the fact that specific things she may have imagined for your future might not happen, or might happen in a way she didn’t expect. Especially since you say she relates to you a lot through trying to encourage femininity, she might take your identity as a rejection of her idea of womanhood, or may mourn an imagined scenario of helping you shop for a huge fluffy wedding dress, or something else along those lines.

Ideally, though, she will do her own mourning/processing on her own time; she may have a lot of feelings surrounding your identity and your transition process, but those are hers, not yours, to manage. If she tries to suck you into being her therapist, do not go down that road with her! You really don’t want to be in the position of having to apologize to her for doing what you need to do to be happy. It might be helpful for her (and your dad) to look up a PFLAG chapter or similar support group for parents if there’s one in your area. Depending on where you live you may have luck finding a regional group as well; I found several in various parts of the US using a search for variations on “transgender parent support group.” (I am not as familiar with non-US resources, but if you are located elsewhere and want to give a general location in the comments, I can try to find something near you.)

This period of time might be really painful for you, and I’m really sorry if that turns out to be the case. It can be really hard to predict how people will react in this situation, and sometimes even folks who eventually wind up being great allies will say incredibly hurtful things at first. My dad has told me on more than one occasion that his opinion on trans and queer issues in general changed completely once he realized that “those types” were actual people with names and faces, including one of his own children. My own experience coming out to my parents was a bit of a disaster; I wanted to wait until after a big family reunion to come out to them, but at the time of the trip I had been on testosterone for five weeks, my voice had just started to change, and I was insisting that everyone call me by my now-legal name.

As you might imagine, my plans to stay under the radar during several days of Family Togetherness did not go so well! On the last day, my dad cornered me and basically badgered me until, completely unprepared and unscripted, I came out to him in the most awkward, disjointed way I can imagine. I did a poor job explaining myself to him, and I didn’t even get a chance to talk to my mom directly – he insisted on telling her himself, and I don’t even know exactly what he said to her. Things were really awkward after that! My mom called me, crying, and asked me to stop taking testosterone, and my dad’s initial research apparently just turned up porn sites, which he somehow assumed were an accurate representation of trans experiences.

Our relationship was uncomfortable and strained for a while, especially in those first few months. But several years later, while things right now are not quite perfect, they’re much better than I had initially imagined. Eventually, we came through the worst of it with a much better understanding of each other and of how we were going to relate to each other as adults. So even if you feel like it does go poorly, you may find that things improve once your mom has had a chance to process the situation, get over any feelings of loss she may have, and see how much happier and more comfortable you are as your transition progresses.

The goal here is for you to have the space to find out what *does* fit and feel right to you.

The earliest parts of my process of coming out to friends and family and starting my social and medical transition were pretty confusing and stressful. The fact that I had space to figure things out while living and spending time with supportive people made the entire process a lot easier. If you’re stuck living with your parents and the situation at home is either actively hostile or just plain awkward for a bit, it’ll be even more important to find outside sources of support.

What does your general support system look like right now? Do you have trusted friends who can offer support or, at the very least, listen with a sympathetic ear if you need to vent about your parents? I think now is a great time to look at your self-care practices and make sure you’re doing everything you can to be good to yourself.Is there an LGBTQ center in your area that offers support groups you could attend? There are a lot of great online spaces for trans folks and I don’t want to discount them, but I personally find in-person support groups to be a lot more helpful. The quality and usefulness of these groups can vary based on who’s attending and what you want to get out of them, but if there is one near you I’d give it a try to see if it’s a good fit.

I’ll also note that some queer community centers that offer support groups will also offer job placement programs; this might be worth a look as well. There’s some good content in the archives here about working through sub-optimal work and living situations; #110#370, and  #449 are a good place to start.

Bruce Campbell looking bloodied and confused.

Like Ash, I want to help! It just takes me a second...a long second...to figure out how.

Question:  How is coming out to your family like admitting that you’ve never seen The Evil Dead in a room full of nerds/filmmakers/filmmaking nerds?

Answer:  Those two things are in no way similar. Which is why I called in reinforcements for this question. Please welcome Julie and Jessica, the filmmaking duo known as King is a Fink.  They don’t need secret identities or quasi-military titles because superhero is their day job.

Dear Captain Awkward,

My family is great compared to most–my parents love us, my relationship with my siblings is good now that we’re all adults, we’re financially stable, etc. But I’ve had persistent problems getting them to stop making homophobic, racist, and/or sexist comments. When I tell them to stop, I usually get hit with the “it’s a joke, lighten up” excuse, and because there are more of them than there are of me I’m very quickly overruled.

Two out of the three categories are personally hurtful to me because I’m a gay woman, not that my family knows it (er, the gay part, I mean). Their casual homophobia so pervades all our conversations, especially the ones I have with my siblings, that I’m far too scared to come out to them. Unfortunately, this also makes the tactic of “this is personally upsetting to me, please stop talking like that for my sake” too frightening to use.

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I have a dream that someday all dads will shine only love and acceptance on their queer kids.

Dear Captain Awkward:

I’m not in an awkward situation yet, but I probably will be soon, and I want to be prepared for the awkward. My current fiance is probably going to be starting to transition into being my fiancee pretty soon. This is not a problem for me. However, I think it will be a problem for my dad, who is kind of controlling and generally bigoted especially about gender and sexuality.

He was NOT HAPPY when I told him I was bi, (I now identify as pansexual, but I didn’t know what that was at the time.) He said a bunch of stupid things, and then mostly seemed to be over it, or assumed it was a phase when my girlfriend and I broke up. He was even less happy when I told him I didn’t believe in his God anymore, but once again managed to deal after much arguing and stubbornness on my part. When I told him I was in an open relationship and had a boyfriend in addition to said fiance, there was less yelling, but he did tell me that he thought I was steering the car of my life into a tree, that my lovers are untrustworthy sluts and implied strongly that this could only end in tears and STDs for me. However, he was magnanimous enough to let me know that when I came crying to him about my poor life choices, he wouldn’t say “I told you so.” (Can you tell I’m still a little pissed about it?) He hasn’t continued to object, but he’s definitely not over it. For a while I thought he was going to stop speaking to me altogether.

He’s also said some nasty shit about trans people in general to me. What I’m saying is, dude has a bad track record. If he decides to out my fiance to people who don’t already know him out of spite or just pig-ignorance and general asshattery, that could be really really serious and a safety issue for him. I feel like I might have to cut Dad off for that reason. Our relationship has never been very good and required many years of therapy to deal with, so if I did cut him out of my life, a part of me would say “and nothing of value was lost.” But despite how crappy he’s been to me, I know he loves me and wants the best for me and all that. He just thinks I can’t figure out what that is on my own. So is there something else I could do that won’t risk my love’s safety? And if I do need to just bite the bullet, how do I tell him to gtfo now that we’ve got an uneasy truce going on?

Thanks for your help,

Daddy Issues

Dear Daddy Issues:   I’ve turned your question over to a trusted advisor who has definitely walked a mile in your shoes, so I’ll just say congratulations on your engagement and let our first ever Guest Poster take it from here.  Love, Captain Awkward

Greetings and salutations, Daddy Issues! I am Lieutenant Trans, a support troop from the Captain Awkward army who has direct experience with transitioning, living poly, coming out to family, and repairing communication with parents after estrangement. Reading your letter, I actually see two separate issues: first, your relationship with your Dad is strained; second, you have a partner who is transitioning, which requires you to now ‘come out’ as well to your family and friends. Your partner is generally absent from this letter, so my first piece of advice is to go to them in a low-pressure manner and say, “Hey, I’m thinking about how to talk to my dad about your transitioning, so I want your guidance on how to go about this – what are your suggestions? What is the best case scenario and worst case scenario, and how will we respond to the latter?” Let your partner marinate on those questions, while you focus on your own relationship with your father.

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