Overthinking It

Dear Captain,

I’m in my early 30’s. Having spent my 20’s doing the ‘right’ things (college -> law school -> office job), I have now recognised what was clear all along, namely that this is not for me at all, and that maybe that’s okay. I’ve also realised that maybe it’s okay to not be making the maximum amount I possibly could be, and okay to say ‘no thank you’ to the budding career I have zero interest in in favour of pursuing my passions.

Passions, of course, don’t pay very well, certainly not at first and possibly never. If I quit right now, today, I would be living hand to mouth with virtually no safety net. If I hold on for another 22 months, then I would have a very substantial safety net, enough to cushion me for a decade or more to come (I would still need to work to feed myself, but I would be able to absorb a good number of unexpected financial blows before going into crisis mode), plus put me in a better position in old age. There is no in between here.

Herein lies the quandary: I could die in six months’ time, in which case I would rather quit now and take my chances. On the other hand, if I did quit now and then didn’t die shortly afterwards, 2020!Me’s life is likely to be significantly more precarious and uncomfortable than it would be if Present!Me stays for the 22 months. I should add here that I tend to be a lot more productive in the creative area I want to pursue when I feel immediately secure, so this isn’t even just about my own comfort, but potentially impacts the quality of the work I want to do (and of course the point of this whole exercise is to give myself a better chance of producing quality work).

Knowing myself, I will probably do the 22 months. I don’t hate my job, have no reason to expect my imminent demise beyond the fact that it could happen to anyone, and the job comes with a fixed end date at the end of the period, so I’m less likely to fall into the trap of just putting it off and putting it off until it becomes too late. I’m just having a hard time reconciling myself to the ‘what if’ part right now right now. Help please?

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Hey Cap,

I have a really close friendship with “Nathan”, who I’m also In Love With. We met on Twitter and talk throughout the day most days, and a long-standing online friendship and flirtation turned into a close offline friendship and flirtation and a gradual but big escalation of my feelings. Long story short, despite mutual expressions of attraction and romantic interest things never went anywhere due to what he frames as general fear and ambivalence regarding sex/intimacy/relationships. He’s essentially said that fantasising about romantic scenarios brings him solace instead of torturing him like they do me – anyway my torch still burns painfully bright, I’ve been open with him about this and he’s been understanding, so several times I’ve taken breaks from communication/hanging out to focus on sorting myself out. It’s still an issue but less so than it used to be, and we remain close friends in constant contact and we see each other when we can (we now live in separate cities).

The issue is that Nathan is very, very, very attractive and he has many, many other online admirers, many of whom run in similar Twitter circles. Our friendship/flirting is well-documented publicly on there and a lot of our thirst followers have filled in their own mad libs about our relationship or at least see me as someone safe to talk to who knows him well and regularly try to probe me for (sensitive/creepy) information about him and his availability. This brings up a lot of knee-jerk Bad feelings of sadness, regret, jealousy etc and I would like to find better ways to ward off these kinds of questions entirely. I tend to maybe go all-in with my response describing my history with him which might do the trick in getting them to shut up about it but comes off as highly territorial which is something I don’t want to be. He’s a private person and I want to protect him but I also want to protect my sensitive, foolish heart and set up some kind of flag in conversations that says “Don’t Ask Me About Nathan It’s Creepy And It Hurts”. Any scripts for how to do this? I feel like I’m stuck in a Jane Austen situation.

– Lovelorn Go-Between

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Dear Captain Awkward:

The academic institution where I work has a counseling center, and offers appointments for staff members at a slightly discounted rate (they’re open for the public, not just people connected to my institution). I’d been seeing one of the counselors there for a little over a year, though I’d make appointments week by week; I didn’t set up a standing one or anything. Well, my last appointment was set for mid-November, but she had a sick kid and canceled, and I said I’d get back to her about rescheduling and well, now it’s 10 months later……
I’m not seeing anyone else, and though I think maybe I should it’s just hard to start. and it’s hard to want to go back to my original counselor. [ I’m not sure we had the same goals, and I’m not sure if that’s okay. Like do the client’s goals always trump, or should I be listening to her cause she’s the expert?]

Anyway, all that aside, I see her a few times a week pass my office, and I feel bad for just stopping and not saying anything and it’s not a bridge I want to burn, but maybe it’s fallen down now? Can I send an email? What should it say? Just, “sorry I ghosted, but I’m okay-ish”? Or “I just haven’t been able to make the time/financial/emotional commitment this year”? “i hope you found someone else to make up that income”?
Don’t know how to end
(Female pronouns for both me and my counselor)

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Every month (thanks to nice Patreon supporters!) we examine the things that people typed into search engines to find this place.

1. “My bf is younger to me by two years and is half bald..but still he criticizes my looks.”

Criticizing your partner’s looks is not a good dynamic. What would it take for both of you to decide “I like the way you look and will say only nice things about that“? Because that’s what you deserve.

2. “My husband hates when I masturbate.”

Has he explained why it bothers him? How does he know when you do it? Does he masturbate? What’s your sex life like together? What would happen if you masturbate anyway?

I think that the relationship you have with your own body is your business and even if he is uncomfortable with it you should still do it! But before anyone issues ultimatums or makes “rules” for the other person, it’s worth getting to the bottom of what this is really about. Control? Envy? Feeling left out?

3. “Tried to be friends after relationship but it didn’t work.” 

Sometimes it just doesn’t work. Here’s a poem:

Friendship After Love
After the fierce midsummer all ablaze
    Has burned itself to ashes, and expires
    In the intensity of its own fires,
There come the mellow, mild, St. Martin days
Crowned with the calm of peace, but sad with haze.
    So after Love has led us, till he tires
    Of his own throes, and torments, and desires,
Comes large-eyed friendship: with a restful gaze,
He beckons us to follow, and across
    Cool verdant vales we wander free from care.
    Is it a touch of frost lies in the air?
Why are we haunted with a sense of loss?
We do not wish the pain back, or the heat;
And yet, and yet, these days are incomplete.


4. “How can I make my make my male crush whom we’ve been been chatting come visit me?”

There is no making, there is only asking. “Would you like to come visit me?”

5. “My boyfriend keeps following me wherever I go.”

This is creepy and smothering. What would happen if you told him you didn’t like this and asked him to stop?

If the thought of asking him to stop is scary to you – you can imagine him being furious or refusing to stop or “punishing” you somehow – think about calling a trained person and talking through some ways you can safely get away from this guy and his behavior.

6. “How to write a long overdue apology.”

Keep it simple. “I realize this is long overdue, but I want to tell you how very sorry I am for (what I did). I hope you are well. Sincerely, (you).”

Don’t ask the person for anything, don’t justify, just say you’re sorry and be specific/take ownership of what it is that you did to hurt them.

7. “How to say no after you’ve already said yes.”

“I know I said I would (do the thing), but I thought about it more and it turns out I won’t/can’t/don’t want to/won’t be able to. So sorry for the confusion/inconvenience/change of heart.”

8. “Husband always asking if I’m okay.”

Some questions come to mind:

Are you okay? Is everything okay?

Is there a question you wish he would ask instead?

Is there an elephant in the room?

Does he think that you seem tired/sad/down in the dumps/cranky/not quite yourself/are you behaving in a way that would make it seem like something is not okay?

Is HE okay? Like, is he asking you if you are because he wants to talk about something but doesn’t it want it to seem like his idea? Is he a particularly anxious person?

This could be an annoying tic he has or it could be that he’s observing something about your health/happiness and wanting to check in. Figure out the subtext of what this question really is.

9. “How I can creep sex my friend.”

a) Watch this video. Put on your Halloween costume. Ask your friend to put on their Halloween Costume and if the two of you can have sex with you while you both have your Halloween Costumes on. Creepy, right?

b) Go to Scarleteen. Read every article on the site. Especially look at anything about “consent.” Don’t have sex with anyone until you fully understand consent.

10. “Short story on boss seducing his junior wife for promotion.” 

I think the site you are looking for is called “Literotica.” It should have come up on the first page of search results, but, anyway, you’re welcome.

11. “Why does my mom find something negative in all my boyfriends?”

I don’t know, maybe but it’s worth asking her this directly. “Mom, why do you find something negative to say about all my boyfriends?” It could be she thinks that you have terrible taste, it could be that she thinks that you want her opinion, it could be a control thing. Has she noticed this pattern? 

12. “Staying with him just because he was your first sex.”

Staying with someone maybe needs more/better reasons than that? Ongoing, current reasons, like being in love and having a healthy, good relationship that makes you feel great in the present day?

13. “A guy who is still on dating sites after he proposes to you.”

This is definitely worth talking about. “Why are you still on dating sites even though you want to marry me? Can you help me understand?” Make sure you both have the same needs & assumptions around monogamy, commitment, what “cheating” is and isn’t, transparency, flirting, etc. and that you’re both comfortable and on the same page with this before you get married.

If he says he’s just looking for “new friends,” please remember: MeetUp.Com exists. There are ways to find new friends that are not dating sites and that don’t make you feel suspicious and uncomfortable.

14. “How to tell your son his girlfriend is not right for him.”

Realize that you only really get one shot at this, and that the end result might be your son distancing himself from you instead of leaving her. Is she mistreating him? Is your worry for him worth the risk of having him turn away from you?

Son, I know you love (girlfriend), but ever since you have been with her you seem really unhappy. There seems to always be conflict in your relationship, when I’ve seen you together she doesn’t seem to treat you with kindness or respect. I know as an outsider I don’t have the whole picture, but as someone who loves you and wants you to be happy, I don’t feel right staying quiet when I can see that you are suffering. I love you, and I’ll try my best to accept (girlfriend) for your sake as long as she’s in your life, but I hope you’ll think about what I said. You deserve to be with someone who treats you well.”

15. “9pm to 4am sexing”

Change your dating profile name to “Diligent Night Owl”?

16. “When a boyfriend wont introduce you to anyone in his life.”

This is never a sign that things are awesome, is it? Either something is fishy, like, he has another partner or spouse and you are a “side” relationship, or something is really messy with his family & friends and in trying to “spare you” the “drama” he is making you question his commitment and your place in his life, or he wants to keep you a secret for some reason. If you aren’t a Capulet and he isn’t a Montague and your families aren’t mortal enemies bent on mutual death and destruction, ask to be introduced. If he won’t introduce you, ask him directly, “Why not.” Maybe stop seeing him if he refuses or if the answer does not satisfy you.

Hi Captain,

I realize my problem isn’t as serious as other letters you’ve answered, but I figured I should try writing anyway since I don’t really have anyone to talk to about it.

I was friends with someone I’ll call “Oakley” from elementary school through high school. It was very rare for my parents to allow me to hang out with friends, so I really only got to spend time with Oakley if I was in one of their classes. The lack of contact outside of school didn’t exactly cultivate a deep friendship, and I didn’t keep in contact with them after graduating even though we only live a few miles apart.

This past weekend, my mother ran into Oakley’s mother at a movie theater, and they talked about getting together for lunch in the near future to catch up. I’m worried this catch-up-lunch is going to end with an obligation for me to hang out with Oakley.

I have nothing against Oakley personally, it’s just that: 1) School wasn’t a nightmare for me, but it wasn’t a great time either, and I imagine it being at least a little painful to have to reconnect with any part of it. 2) While I remember Oakley fondly, they’re essentially a stranger now, so what’s the point? And 3) I have no interest in socializing with *anyone.* (I made more “friends” in college and the following internships/jobs, but I avoided spending time with them outside of those contexts. I do wish I had real friends, but the idea of socializing makes me extremely anxious.)

I already asked my mother not to set up any “play dates” between me and Oakley (she was surprised and said it was a good thing I told her). I’m not sure what else to do or what she could say if Oakley’s mother brings it up. Any thoughts or advice?

(Note: I realize Oakley might not be interested in seeing me at all either. I’m just imagining a worst case scenario where Oakley’s mother tries to reconnect us.)

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Dear Captain,

I’m 25 years old and when I was 21 I got my first tattoo. It was a memorial tattoo for an uncle and I’d been thinking about it for a few years, so finally I decided to do it. My mom took me to her tattoo guy and after it was done I posted a picture on facebook.

Now, my grandmother hates tattoos, and I didn’t tell her about it beforehand, so she found out on facebook. Two days after getting the tattoo and posting about it, she called me to tell me how disrespectful I was for not telling her about the tattoo, how hurt she was to have found out about it on facebook, how my mother and I are so disrespectful toward her and what’s next? Is she going to find out I’m engaged on facebook, too? Why didn’t I tell her I was planning this? I didn’t know what to say, but after the phone call ended I cried and felt like an awful, terrible person. It had been 100% intentional to not tell her beforehand, because I know my grandma and she would’ve seen me telling her I was getting a tattoo as a discussion about whether or not I should get a tattoo. I knew she didn’t like them and I didn’t feel like being lectured. Moreover, I didn’t want to pretend to ask for her permission because, at 21, I didn’t need anyone’s permission to get a tattoo in memory of my dead uncle. (I should note that this uncle was not her son, but her ex husband’s brother, and a good friend of hers.) My mom got super upset with my grandma about the phone call, saying that she was trying to make me feel guilty, and they talked and nothing was resolved but we sort of came to a peace about the issue. My tattoo isn’t visible, so she never has to see it, and I never mention it around her.

Almost two years ago I got a second tattoo, this one on my wrist. It’s visible. My mom once again took me to her tattoo guy. It was a week before Christmas. We decided that for the sake of peace I’d wear long sleeves to Christmas dinner.

But I still haven’t told or shown my grandma that tattoo. I’m afraid of another incident, and I know the longer I put it off the worse it’ll be, but it feels like it shouldn’t matter? I’m an adult. I barely told anyone about the first tattoo beforehand, and I didn’t broadcast the second one; people have found out about it as they’ve seen it. Maybe I should’ve told my grandma that I was getting the second tattoo before I got it, but that felt too much like asking for her permission – which, again, I don’t need. But I don’t want her to get upset again and act like I’m a terrible granddaughter over this. I want to get another tattoo, and I want to be able to be around my grandmother without choreographing my movements so that she doesn’t see my inner wrist. Should I sit down and have a conversation with her? Should I just say fuck it and let her notice when she notices? Am I a terrible granddaughter for hiding a tattoo from her for almost two years?

(I feel like adding that my mother has two tattoos, and three of my grandmother’s second husband’s grandkids – her grandkids, basically – also have tattoos. Two of them are younger than I am. Was there any reaction to their tattoos? Of course not. Just mine.)

Potentially Terrible Granddaughter

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Hi there,

I have a bit of an odd quandary. I am divorced, and I divorced young. My relationship was a very bad and abusive one, and that was a dark time in my life. I have gotten therapy, learned a lot about myself, and I think I’m doing well. It’s daily work to deal with lingering issues, but I typically feel most comfortable addressing those to my therapist or close family who knew me then. It’s intensely personal to me, and revisiting it in casual conversation isn’t something I’m interested in doing. I have PTSD, and it coming up usually sets me up for a good day of feeling anxious and awful.

I’ve since moved across the country and none of my new friends really know much about my divorce or that I was ever married. I don’t hide it, and a more in-depth peruse of my social media probably holds some clues, but I don’t proactively bring it up. I’m an age where many of my friends are getting married and navigating serious relationships for the first time, so it’s very plausible and even likely that none of this ever happened. People assume that (I never lie), and I don’t correct them.

That said, I’m fortunate that some of these relationships are becoming closer, which raises two issues:

1. It is normal to not tell a minor acquaintance your life story, but it is starting to feel like a purposeful omission to people whom I see often and confide in me. I know I’m not obligated to share it, but occasionally they’ll find out and when they do there’s a bit of “whoa, that was a pretty big thing to leave out.” I stammer and ineffectually mumble some sort of half-apology, but I have no idea how to even start. I don’t feel like I need to apologize, but I always feel like I kind of lied, even though I didn’t.

2. I’ve been asked, directly, a few times – “were you once married?” and I don’t want to lie. I also, however, want to be clear that it isn’t something I enjoy talking about without disclosing more about the relationship than I’d like to.

I want to set a boundary, I don’t want to lie, and I don’t want to sensationalize. I feel like I need to give a reason why I never said anything, but that gets into self-disclosure I’d rather avoid (“Yes, I was, but it was a difficult and painful time and not something I talk about” generally creates pity and curiosity and gossip and more prying, all awful.) Not giving a reason or changing the subject generally creates a weird, stilted conversation or doesn’t adequately communicate that it’s off-limits so then it comes up again.

I need a polite way to communicate that this is not a secret but not something I talk about without making it into a bigger deal than it is and not making anyone feel as though I’ve slighted them by leaving that out. I’d love to have scripts for either of these instances because right now I’m just floundering, it’s awkward, and it’s starting to become the elephant in the room, and I’m sad I can’t think of something better to say.

Thank you so much. She/her pronouns.

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