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terrifyingly amazing

Dearest Captain,

I’ve been dating a person for almost 3 months, and he is terrific and lovely. Sexy stuff is also ding ding ding jackpot!!!. I’m at the point where I would like to have a low-stress check-in about how we’re both feeling regarding exclusivity and commitment. I know we’re both currently not seeing anyone else. My general impression is that he’s interested in a relationship, but ‘impressions’ are not hard evidence and I just want to address it explicitly without my inner FEELINGS-VORTEX getting in the way.

I’m really struggling to find the right words to initiate this conversation, because everything that pops into my head has strong overtones of “PLEASE LOVE ME FOREVER” and “I’m putting all my hopes and dreams on you despite only having known you for 10 weeks or so”… and those are NOT the kinds of conversations I want to have. They’re definitely not representative of how I actually feel – it’s just that my anxious-attachment mechanism kicks into overdrive at the very thought of addressing it and everything starts to feel like much higher stakes than it really is.

I did some googling on “How to have a DTR conversation” or similar, and Captain, there is a universe of terrible advice out there. Of course, much of it is geared towards straight women, and either implies or outright says things like “Don’t be too pushy. Men don’t like to be rushed. Let him do the chasing.” DON’T STARTLE THE WILD MALE HUMAN. There’s a heck of a lot of cultural messaging to the effect that [in a heterosexual relationship] it is a woman’s role to push for commitment and that men dread this conversation, which makes me both extra nervous about it and also kind of resentful. I would like to be able to leave those feelings at the door when I bring it up, but I’m so lost for the right words to use that I just end up getting even more anxious, and then I don’t bring it up at all because I want to be coming from a place of curiosity and confidence, not from a place of fear.

I’m sure about this guy. He’s kind and responsible and we laugh together a lot and we are hella attracted to each other. I’ve felt a whole bunch of YES about him since we first met, and know that I know him a little better I feel totally sure that I want a committed relationship with him. It’s frustrating and embarrassing for me that I feel so lost as to how to bring this up. I know there’s no one-size-fits-all approach, but do you have any good scripts for having this kind of conversation? I think you’d be doing the world a great service by putting out a few (non-gendered) ways to check in with someone you’re dating about your hopes and feelings about the relationship.

Many thanks for all you do,

Looking For Words
(she/her/hers)

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Hi Captain!

My problem is one that I imagine is very, very common, but I’ll start with a little background on my specific situation.

I recently started going to therapy for some pretty serious self esteem issues that had led to me isolating myself for a long time. Up until this year I hadn’t been to a non-family social event – including just one-on-one hangs – in over five years (and even before that it was pretty rare).I’ve made a lot of progress over the last few months; I have a few good friends that I can go out with and all in all, I have learned how to get better about relentlessly judging myself during and after every social interaction.

But even after all this (successful!) work, there’s one aspect that I just can’t seem to crack, even with my wonderful therapist, which is the possibility of a romantic relationship. It has been ten years since my last relationship (I’m in my early30s) and I haven’t been on so much as a date since then. While I was in my hermit state I vacillated between “I don’t really want a partner anyway” (a big fat lie) and “You’re not worth a relationship.” Basically the idea of being involved with someone in a romantic way seemed to be something that just wasn’t in the cards for me, ever. I always pictured myself alone.

Now, though, that I’ve started being around people socially, it’s starting to seem…not so insane. Like maybe it’s not out of the realm of possibility anymore, at least not when I think about it in an abstract way. But when it comes to a practical way – joining a dating site, talking to guys at social events, whatever – I can’t seem to break that bubble of “Why even bother? Who would want to be with you?” Even just writing this part of the letter made me feel embarrassed and silly.

There’s one important thing at play here that I haven’t mentioned yet: I’m fat. [details of weight redacted by Captain Awkward, per the site policies] I just can’t stop thinking of my weight (and looks in general, to a lesser extent) as my #1 defining characteristic.

It’s pretty easy to draw a straight line directly from media portrayals to my issues in this area. A fat girl talking about sex is almost always a punch line, a character for everyone else to make “ew, gross” faces about. Despite intellectually knowing better, I’ve internalized this message. For instance, occasionally I’ll use Tinder when I’m bored or feeling optimistic about the future (but mostly bored), and one time I ran across a co-worker. What should have been a “haha isn’t this awkward” moment sent me into a complete meltdown. I was *mortified* that this co-worker might think that…I don’t know, that I thought someone would be attracted to me? It was ages (like, literally a year and a half) before I could be around this extremely nice co-worker without wanting to crawl under the table and die. I couldn’t even talk to him.

So that’s basically where I am. This feeling that, no matter how funny or kind or interesting I am inside, it doesn’t even matter because my outside is so unappealing. I get so sad thinking about how no one will ever look at me and think, “Oh, she’s pretty, I’d like to get to know her”.

How can I start to escape the “overweight=unfuckable, unfuckable=unlovable” cycle?

-Want To Make The Rockin’ World Go ‘Round (She)

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Hi,
I’m a 17 year old homeschooled dual-creadit student who attends my local community college. I have a 4.0 there, and I am part of the honor society and an officer in the Honors Student Organization. I’m not, at least not in by my family’s standards, brilliant, but I am smart. I always try to be a nice person and do good things, but I am worried that I come off as condescending and sometimes bitchy to my class mates. My grades are a large part of my identity because I am so focused on school, and because of that I have a reputation as an overachiever in all of my classes. I use my reputation as, at least somewhat, a defense mechanism. I have never had a boyfriend, had any alcohol,done any sort of drugs, etc. The people in my classes call me a baby because I don’t lie about being extremely inexperienced, and I don’t really mind that. I my be inexperienced, but I am not as naive as they seem to think I am. I use my inexperience as a reason I don’t throw parties when my parents leave me home alone for sometimes up to a week (they both travel for work). I don’t hide my grades from my fellow class mates; in fact, I share them openly. However, sometimes I worry that I come off as condescending because a lot of people make Bs or Cs, which I consider failing for me. I know that considering that a B is failing isn’t healthy, but school is my life and I don’t know how to let it go. I generally don’t understand why people don’t try hard in school and do their best. I understand that a lot of people have a job, kids, or both; but those aren’t really the people I’m talking about. The people I don’t understand are the ones that complain about doing poorly on tests and having to drop classes and then do to festivals on the weekend when they have homework. I also know that sometimes I can see the world in too much black and white and not take into account the environment somebody grew up in. I want to understand them better, but it is so much easier to call them stupid and write them off in my head as a lost cause. How do I learn to think of people as people and try to understand where they are coming from? When should I stop giving them leeway and say they need to step up and try harder? How do I not let my school define myself and my life when they are so important to me? How do I/ should I hold back on what my grades are because I may come off as a insensitive and condescending? Why do some people ignore their school and then freak out because they are failing?

Thank you for your time,
– The Overachiever

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Dear Captain Awkward,

I am mentally ill, to date I have spent 23 days on involuntary psych holds. Most of this wasn’t warranted but that is a whole other thing. I am also a stand up comic and when I am hanging out with comedy peers everything is fair game and no one really shrinks from your dark stuff. You’ve been 5150ed me too lets compare notes. I am looking to date through online sites and assume that this dynamic is not universal. I like to get stuff out in the open as quickly as possible but is this something that warrants first date discloser? 2nd Date? 

I haven’t even started replying to posts of people I am interested in yet and panicking over what to do when this comes up. Therapy and medication have helped a lot but being committed had me feeling like I am a piece of shit and not worthy of love for a long time. A large part of me just wants to never bring it up, but that doesn’t seem fair. I have PTSD and I want any potential partner to know why something might suddenly upset me out of the blue or cause me to immediately need to leave a certain environment or situation. 

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