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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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Dear Captain and Crew,

I am transgender, FtM, or at least that’s what I came out as several years ago. Since then, I have become increasingly isolated due to work, debt, and extremely debilitating mental illness. I’m doing my best to sort those things out (moving to a place where friends are, looking for a new therapist), but I don’t really know anyone who gets the trans stuff – I always have to be the teacher. So it’s hard for me to talk about my confusion, and my very pronounced internalized transphobia. 

I feel like a monster. Like even without all the mental illness, debt, and isolation, there is no way anyone could ever love me, because I’m trans. My family has been pretty good (and by good I mean awful) about reinforcing that trope.

I’ve spent a lot of time alone the last few years, and now, I’m not even sure if I am trans. Or maybe it’s just that the social cost of being trans outweighs the benefits of feeling more comfortable in my body. Does it matter what your gender is when you never leave the house? The impact of looking for housing while trans, applying for social assistance while trans… even just using public washrooms – I feel like it’s worn me down so much. So I can’t tell anymore if I’m not trans (and was wrong before…?) or if I just am so damn tired of how it feels to be trans in this world. 

I don’t know how to stop hating myself, and how to stop thinking of myself as unlovable when everything in this world seems to tell me that my name and my body and any discrepancies between them make me a freak who can’t function in the system. How can I imagine a future for myself? 

So I guess my question is – how can I tell what my gender is, when 99% of how I think of my gender and how I perform it, is centered around other people – around my safety and ability to navigate the world? How can I know what’s truly there underneath? (And does it even really matter?) And do you have any recommendations for dealing with internalized transphobia? I’m trying to read positive, feminist FtM stuff, but it mostly just makes me angry, because I don’t understand how they can all seem so happy. 

Thank you,
Trans?Phobic

Dear Trans?Tired,

Hey there, it’s Lt. Trans aka A. Raymond Johnson. I did something terrible and changed your name without permission, which isn’t cool since as trans people, we have to deal with being misgendered and misnamed all the time, so I apologize for that. But I needed to right away confirm and validate your feelings of being tired of being trans. That isht is indeed exhausting. And you seem to be in a particularly bad run of it right now.

I wore the HELL out of this record as a kid. This explains some things.

I wore the HELL out of this record as a kid. This explains some things.

I totally get feeling like a monster. Read More

Dear Captain Awkward,

First of all I’d like to say that I’m not even sure if this is a problem or if I’m just making problems up because clearly SOMETHING in my life has to be going wrong (I frequently second guess myself, but that’s a separate issue) but here goes anyway. I was born with a male body, but I’m not entirely sure that I was born with a male mind. It’s not always an issue, hell, a lot of the time I don’t even think about it, but when I do I realize that I may be happier if I were a girl. Part of me thinks that this may just be some sort of “grass is always greener” issue, and I’m suffering from the delusion of “well if this one thing were different all my problems would go away”, but I don’t really think it would solve everything, I think I just might be more comfortable in my own body that way.

I am currently 18 so I don’t know if this is just a body still changing I’ll settle in eventually thing blah blah blah HORMONES thing or not. I have talked briefly with my mother about it (she is an incredibly open minded woman, so this wasn’t TOO difficult, though there is still always going to be some sort of fear there) but the main thing I remember getting out of that is her wondering if I really should be female or if that is just the result of me growing up in such a liberal, open minded area and being receptive to the idea. I am certain that she would have no problem with me really being a girl if we knew for a fact that I should be, but that’s still not the answer I wanted from her (not that I know what I really did want). I guess what I’m asking is is there some way for me to figure this out? Am I just making extra problems for myself? Am I just looking for fantasy solutions to magically make me feel better (when in reality I would feel no different if it were the case)? Is it normal to be this on the fence about something like this? One last thing, I don’t feel extremely WRONG being male….. I just don’t feel entirely right, either.

Sincerely,
Dazed-and-Confused

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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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