Dear Captain Obvious,

My mom has always been on about how I look, but since I’ve turned 16 it seems to have gotten worse. She got me a fitbit that she makes me use (which I hate because it tells me I eat too many calories a day, even though it’s the recommended amount), made me diet with her, and constantly makes comments on how “I should go to the gym more,” even though I’m a perfectly healthy weight for my height. If i’m about to leave the house with no makeup on, she says “Oh why don’t you put a little foundation and mascara on before you go?” and is visibly embarrassed if she sees m in public wit none on. She also hates me wearing my glasses, as they “cover up my beautiful face” and will make more comments on them if I wear them outside the house instead of my contacts. My boobs aren’t very big, but my thighs are, so she’s always pushing me to wear push up bras and slimming clothes. It’s gotten to the point where I’m embarrassed to not be made up, am starting to obsess over my weight, and am just downright lacking in self-esteem. I’ve tried bringing it up before, but she either plays the victim or pretends like she never did any of that. Any advice on what I can do?

I’m only 16. I’m not a model.

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Ahoy, Captain,

So, the holidays are coming, and there are some issues which I am pretty well obligated to deal with, but have not yet (being a weenie, largely), here’s a list of facts:

– I am transgender
– I have started hormone therapy (testosterone), my voice has dropped noticeably, I should probably shave, and an awful lot of people in the community call me by a different name, and he/his pronouns
– I am closeted to one rather conservative maternal vulcan uncle
– I am closeted to both my maternal and paternal grandmothers.
– I am known to be transgender to my other uncle, and his wife and children
– both grandmas live within a kilometre of me
– I am 24

My maternal grandma is essentially the matriarch of the family. It is considered unspeakably rude to point out when she is wrong. She doesn’t know. I’ve tried to tell her, she lives very close and I see her at least once a week, but she’s very conservative, likes being in denial about things she doesn’t like, and is starting to develop Alzheimer’s. Either she ‘forgot’ or she forgot. So, how do I tell all of these people? How do I deal with this at the holidays? Should I just shave, put on drag, and count on everyone around me to ignore the obvious? Being trans is an obligate coming-out, so I know I can’t put this off forever. If not this year, I have to deal with it next year, and short of moving overseas, I don’t know how I’d avoid that.

– A Transponder

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Hey Captain Awkward!

First off, I hope you’ve had a lovely holiday season so far! Hopefully it’s been less stressful than mine.

I wasn’t able to quite find an answer to my situation (and I admit, it’s sorta weird). Basically, shopping for the holidays has become quite an event. Maybe it’s because my family’s Asian, but I feel like often times the value of the gifts is measured by how much or how little is spent.

I’ll give you an example. My mom’s birthday is on the 19th, so having a birthday and Christmas close to one another means double-trouble for gifts. My mom says she doesn’t care about “expensive” things, just so long as there is “effort” put into the gift. Last year I had purchased her a bunch of succulents and a terrarium set for her birthday and a fair trade sculpture of a church building for Christmas. She loved them both, but demanded the price for each. The birthday gift was around $40 and the sculpture was $15. Hearing the price, she was immensely pleased with the sculpture and loved it more but said that the succulents/terrarium lost “value” because they cost “way more than she was willing to pay for them.” What? She appears to be the worst at this, followed by my brother (who seems to have picked up her habit). My dad seems to be the complete opposite and in the same boat as me (aka: stressed out about buying gifts because the price is scrutinized).

So this year – thanks to the fact that I have a job and am making a decent amount of money – I got her a custom wooden bowl thanks to a close woodworking friend of mine (it’s super fancy with carvings and copper inlay) for her birthday (a $120 value, but my friend only charged me $60 despite my insistence that I pay him more for it) and an iPad Mini 4 split between my brother and I.

The iPad Mini has its own separate issue – I had purchased it from the Apple Store for $400 (adding in the case it totaled to $440). When I had messaged my brother the cost, he flipped out. Said it was way too much money for an iPad Mini and chastised me for not going online and buying it from Best Buy (where it said it would cost $300). He told me that the value of the gift had been lost because I was “wasteful with money,” “was giving away $100 for free,” and that “Mom won’t like it because you spent way too much.” Kept going on about how he’s right and I’m wrong, and even threw in a weird analogy (I quote, verbatim): “Say it’s your friend’s birthday. You wanna get him or her a pencil. You find two pencils exactly the same. One is 1 dollar. The other is 101 dollars. Which one do you buy?” Um, what?

I ended up returning the iPad Mini and purchasing it and a case online (for $340, and yes, we saved $100). But I didn’t expect to get shat on for the $100 difference. Sure, I’m wrong in that I should’ve bought it for less, but I didn’t expect to be berated by my younger brother about how I’m being reckless with money when I really only spend money on friends/family the holiday season!

I feel like I put a lot of thought and effort into finding something that my mom wants/likes/needs. The same goes for my brother (he’s getting a shirt, a phone holder for his car, and a pair of Nike running shoes). Yet I feel like worrying about the “value” of things has almost ruined the spirit of Christmas (though my brother said I have ruined the holiday spirit and am using this as an excuse to recklessly spend).

I’m getting incredibly anxious for when Christmas happens, and I guess my question is: how do I handle the potential “tsk tsk” when Christmas gifts are exchanged and opened? I feel like if this Christmas turns out to be a dud, I’m just going to stop investing in giving them certain things, but then I know I’ll be chastised for not caring enough in giving them something of value. How do I handle the awkward situations when they arise? My dad will probably keep quiet and agree with whatever my mom says, but this whole thing is driving me crazy!

Gift$ or $hit

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Edited to add additional follow-up from the Letter Writer below the jump.

Dear Captain Awkward,

First off, I want to let it be known that we are a family of Christians; I believe there is only one true God and that to be saved it must be through Jesus Christ. I have raised both my children “Paul” – 19 years old – and “Mary” – 24 years old – to be strong in faith and put their trust in God.

However, I fear for my daughter’s life. She recently confessed to me (this past summer) that she is seeing someone, let’s call him “Jim.” Jim is not who I want for my daughter and I worry that their incompatibilities and differences will lead to her being hurt.

One, his family is Catholic. We are a Baptist Christian family. I don’t believe in the teachings of Catholicism. Even worse, Jim is an atheist and does not believe in God and I feel that he will drag Mary down spiritually. This is the biggest thing that I am scared of, and while I have tried to tell Mary that she should break up with Jim for her own wellbeing, she will ignore me or pretend I didn’t say anything. It hurts me deeply that she would choose to ignore her own mother like this. She should know that God’s love is not to be taken lightly.

Secondly, We are a Chinese family and Jim is from an American family. I worry that the cultural compatibility will be an issue.

Three, Mary has a masters degree whereas Jim has only his bachelor’s. I feel that he will come to resent my daughter for having a higher education since he is the man in the relationship (and I have seen many relationships end because of this).

Four, I am scared that he will be a bad influence on Mary. He does not smoke or do drugs but according to Mary he does drink on occasion. Mary tells me she does not drink (she claims she does not see the point) but for how long until she gives into the temptation of drinking? What about peer pressure from hanging out with his family and his friends?

Five, I feel like Mary is settling in life and Jim is a result of that. Another example: She is in a marketing job and they are not paying her very well (only 40K and she has a masters degree). She says she loves it but I don’t think she does, I think she’s just trying to rebel against me. She doesn’t even listen to my suggestions that she move back home to Virginia (she lives in New York) to save on rent or so that I can help her grow.

Six, I am scared that Jim will pressure Mary to do sexual things. I have already warned her that her purity is an important gift from God, but I am so scared that she will ignore my pleas. And because Jim is a man, I am worried that he may rape her even if she says no.

Mary has always been very independent, but she is still young and not mature. I need help in making her realize that Jim is not a good person for her and that she will suffer in the long run as a result from being with him. If she does not break up with God, how can I help lead them back to God so that they can have a Christ-like relationship?

Thank you,
Concerned Mother

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Dear Captain Awkward,

My parents and I have a very strained relationship. There is obviously a lot involved, but since I left home 12 years ago I’ve slowly been setting boundaries with them and trying to have the kind of relationship we can manage (which is a superficial though mostly friendly one as long as I’m not in the same state as them). While a lot of the things my parents do bother me, I’ve been coping with them. However, I have a pet peeve that I just can’t get over, and I need help!

My dad insists on talking to me in baby-talk and in the third person. I am 30 years old, a successful attorney, married, and 100% an adult. He tells me all that time that I’ll “always be a widdle girl to Daddy” and other similar nonsense, and I want to reach through the phone and show him what’s what. I have far exceeded what he thought I would become in life (no thanks to him) and I feel like he’s infantalizing me to ‘keep me in my place.’ I hate it.

But how do I make it stop? This has been going on my whole adult life, and I feel like I’m in deep to just say “actually that bothers me a lot, please stop.” Ultimately I know this is indicative of his whole attitude toward me, which will never really change, but if I could just carry on a conversation were he says “I changed the oil today” instead of “Daddy changed the oil” (in a cutesy voice) I would take it.

Not Widdle and Not Buying It

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Can I say how much I love this LW’s original email subject line: “A Soap Opera Problem–families torn apart over money, demanding parents, undutiful daughters who are me, sons trying to bear the whole burden.” Yeah!!!!

Dear Captain Awkward,

I’d really appreciate your advice on a family problem. Dad grew up
privileged, then was mostly-disinherited and lost his job when I was a
kid. Instead of retrenching, he incurred debt. Mom demands luxuries,
cheats, and is an alcoholic prone to rages. Now Dad asks me and my
brother A for money constantly, always at crisis moments.

Dad always believes that his financial issues will be over soon.
Unfortunately there’s a company he has a part in being sold, meaning
he might get some money one day—there’s some basis in reality but not
enough. He refuses to sell his house, because he wouldn’t get enough
money, and claims to be always economising because he doesn’t go on
holidays though Mom does and he belongs to an elite gentlemen’s club.

A and I have precarious jobs in which we are paid in irregular lump
sums, so we have the money to give him. We both consider ourselves
lucky. The emotional toll of these emergency requests is huge. We also
cannot afford them. Over 5 years, between us we’ve given Dad over

I wrote to Dad saying his behaviour is disordered and deeply hurting
us. He refused to go to his bank with us, blamed A for not giving him
enough, and hardly seemed to have read my message. He’s past hearing.
Saying he’s a good father otherwise is asking Mrs Lincoln how she
enjoyed the play otherwise.

I tried cutting him off altogether years ago: it ended when my
siblings exerted pressure on me to do a family Christmas. I’m proud of
my siblings (A, B & C, all younger) for getting through our childhood,
but I’m the one who rocks the boat. A gives money to Dad without me
knowing, so as not to risk alienating me. A has a more optimistic view
of the situation. My sister B agrees with me mostly, but B and C are
more sheltered (by me and A). C is college age, still living with my
parents. He’s begun suffering from panic attacks. He plans to get out
of the house next year: I’ll help him.

I’m considering not going home this Christmas, but I know it’ll upset
my siblings and I want to see C as neither of us is great at
long-distance. If I do go I’d like a script for talking to A, and my
other siblings, about this, and to make a plan for us going forward,
in how we’re going to react to my parents and stick together. I’ve
asked A to promise me not to give money to my father without telling
me: so far he hasn’t promised. It would make me happy if I could get A
to agree on no more money given directly to my father.

Thank you so much.

–Saving Only Siblings

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Hello! This is a question that is hopefully less fraught than a few of the other Holiday Questions and I hope will be an easy question for you all to answer.

My partner and I have been living together for over a year and together for much longer than that; it is a thoughtful, committed relationship and I’m very happy. My parents took some time to warm up to him but now like him very much (him wading in (yes, literally) to help at last Thanksgiving’s Sewer Explosion in the Parents’ basement went a long way towards them recognizing how good of a man he really is).

The problem: my family is deeply Catholic (not me) (and in the liberation theology, Nuns on the Bus, Vatican 2 kind of way, which helps). Until my partner and I marry, my parents will not allow us to stay in the same bed. We have no plans of getting married unless there is some extenuating circumstance, and then certainly not in the church.

I haven’t brought it up in the last year or so because 1) I want to respect their beliefs and 2) most of the times we’ve been home, I’ve been sleeping on a couch or with my sister anyway since it’s been for other family events where there’s a full house. But now it’s gone on for a long time, and aforementioned sister yesterday got in a fight with my parents about creating a “boys dorm” and a “girls dorm” for our next family vacation (this also will impact my brother and his girlfriend, who have been together since they were sixteen but also are unmarried). They told her that it’s clearly not an issue since I haven’t brought it up and she’s overreacting. She is not.

Look, I’m not trying to have wild kinky sex under my parents’ roof. I would like for my partner to not have to sleep on the floor (or as happened on other vacations, in a tent outside), and I would like to feel like my parents respect our relationship. How do I broach this topic and make it clear that this does, in fact, bother me, but I’ve thus far respected their wishes — but it is a problem that they don’t seem to respect me or my relationship as responsible, adult, or mature without the parameters of Catholic marriage? Do I even bother? Is this a passive aggressive nightmare waiting to blow up ten years down the road if I don’t say something now?

Help me, Captain Awkward! You’re my only hope!

Grandma’s sleeping in my bed this year anyway so it doesn’t even matter right now

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