Author Archives: JenniferP

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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Dear Captain Awkward:

My partner and I have been together for 6 years and we recently moved to another country where I know the language and have some friends. My partner has been focused on jump-starting his freelance career and doesn’t have many friends in our new country, nor does he know the language very well. Over the last few months, there has been some major conflict culminating in a moment when I made him feel stupid and blamed for us leaving an event my friend was having. This was all accidental on my part, but I have taken ownership of my words and actions. Since then he has made it clear that that moment has colored the relationship and he can no longer move forward. He is still here until we go back for a visit to our home country in a month and during this time we have been acting like normal – planning future trips, being in love. I had asked him to give me a chance to show him that I can balance out the past with our future. Today, I asked for an update and although he says that he sees me being a more supportive partner, he still feels like he can’t continue this relationship. What can I do in this next month to “re-color” the relationship? He is giving me this chance because he wants to be with me, but he feels “burnt out”. How do we heal and move forward? Is it possible?

Partner with a Past

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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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free-wedding-clipart-jrtge68ilFriends, Readers, Countrypeople…

I may have mentioned once or 1,000 times: I’m getting married tomorrow.

I won’t be moderating comments for a few days, and the mailbox is temporarily closed.

If you’re on a first-name basis with the gods or the coven or robot wizards who control the weather, see what you can do about clear skies and good temperatures just north of Chicago for the next 48 hours.

Edited to Add: 

  • Weather was PERFECT. Thank you for your sacrifices.
  • Honeymoon’s in March.
  • Weddings =  I get the hype now. People who have known you for your whole life, at every stage, all together in one place, being sweet and hanging out and breaking bread.
  • Thanks for all the well-wishes.




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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Hello, it’s about 10:00 am on Friday in Chicago. From now until noon, I’m going to answer as many short Twitter questions as I can under the hashtag #awkwardchat. Patreon patrons can also submit questions to the post comments there. Turning off comments here until the chat is over to limit confusion (and # of characters/words).

Let’s do this!

“What do I tell myself when I have to memorize, for an exam, things that have proven to be inaccurate or false?” 

Howabout: “Once I make it through this class I will devote my life to setting the record straight. Now, my white-hot anger shall be my memory aid.

Depression, anxiety, and lingering grief and anger from a bad breakup are wearing on me, but I still need to Get Shit Done(tm). How do I approach doing that without ignoring how I am feeling? 

Give yourself permission to grieve for a short time each day. Maybe set a timer for 20 minutes and free-write in a journal in the morning  so that you can indulge the yucky feelings and get them out on the page. When the timer goes off, make a choice to put that aside and focus on the things you need to do. The journal will be there later, or tomorrow, when you need it. If you can make a ritual like this where you have permission to feel your feelings, you might also be able to give yourself permission to put it aside when you need to get things done. When that fails, I’ve heard the Bene Gesserit Litany Against Fear is pretty good.

I’m working through a poly/metamour communication issue. Any tips on balancing different personalities and needs? Also, I’m an “everyone needs to like me gal,” and I often put that in front of whether or not I actually *want* to be friends with this person. The answer to your question is in your question: You’re considerate of other people’s needs, sometimes at the expense of your own. You’re probably a fantastic partner and really good at the negotiations of poly life as long as everything is going your way. What if for the next little while you tried an experiment, where you gently/kindly state your own preferences and let other people do some of the work of balancing? “I don’t want to hang out this weekend.” “I like our friendship just how it is.” “I’m glad you and (Partner) are having fun, that’s great! I don’t want to join your hangouts/hang out with you one-on-one.” “I prefer waffles to pancakes.” 

How does one combine introvert and a very extrovert job (e.g. teaching) without feeling exhausted all the time? Dude. I wish I knew.

Ok, that’s not true, I *know* some ways, I don’t always *do* those ways.

Some strategies:

  • Remember to eat & drink – regular meals, bring a snack, drink water, plan to refuel.
  • Get up early on class days and use that time to prepare/wake up all the way.
  • Use the class breaks to get *away* for 10 minutes. Sometimes I go to the bathroom on a different floor so I can have a few minutes free of interaction.
  • Track energy levels and look for patterns. It’s okay to plan something social for right after teaching – when I’m on and in that mode, I’ll stay on for a while. I will need some downtime the next day, though, so, plan for that if possible.
  • Schedule blocks of time when I look at email/work with students.
  • Simplify other stuff I have to do that day as much as possible.
  • Have lots of teaching strategies on hand – get students working in small groups, get students presenting & sharing clips, get students moderating discussions & their own critique sessions, to give my voice/energy some built-in breaks.

Do you ever regret starting an advice column?

Rarely, if ever. Sometimes I regret that it took me off the road of making movies for a good while, but I love the work and the community. If I could do this as my main job, I probably would.

Ever regret answering a question?

Yes, a few. That one from the anxious guy, which I won’t link to, but if you remember it, you know exactly what it is. A few where I fucked up the advice, missed something really obvious, or didn’t think it through all the way. Some where the Letter Writer quickly became overwhelmed by All The Opinions of The Internet rolling in on their fragile life situation.

I’d love some Ask A Manager-style updates from letter writers. How likely is that too happen with CA?

I do get updates every now and then, some private, some with permission to post, but I never want letter writers to feel obligated to update us. I like Ask A Manager’s updates, too, and I know the woman who wasn’t allowed to pee haunts us all to this day. If you’re reading, we love you and hope you are okay. This sounds like a good January project, though. I’ll see what I can pull together.


Her cuteness is a mystery – if only it came as a serum we could spray on not-cute things to make them cuter! As tempting as cash offer is, she is wrapped around my head like a tiny hat right now and winter is coming.

How do I overcome Resting Friendly Face?

I share your curse. Headphones. Always having a book with me. Helping people when I can, saying (while probably still smiling), “Forgive me but I have no idea! Good luck!” when I can’t. Basically, I can’t overcome it, so I try to live with it and then write a website about boundaries.

I’m going to be out of work to donate a kidney. I don’t have to tell my coworkers why. Pros/cons of telling?

I don’t have pros and cons, just questions.

  • Do you like your coworkers?
  • How gossipy are they? Do you think they are speculating about why you’re out of the office and coming up with weird reasons for it?
  • Would you tell them if you were having another kind of surgery, like, “I broke my foot, need surgery”?
  • Are any of them doing a giant favor by covering for you?
  • Are you going to need any kind of specific help or recovery time when you come back?
  • You sound like a person who is pretty private and who doesn’t a big deal made about you, which seems like a good reason not to tell. Maybe hold off on the specifics until after the fact.









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.