Dear Captain, et al, and Awkardeers,

I have searched the archives and not seen anything like my current conundrum.

Cliffnotes: Former partner at the law firm where I am an associate, Jim, left the firm last year. We worked together for approximately a year, during which time he took lengthy FMLA absences. I haven’t spoken to him in the year since he left unless he dropped by the firm to see the senior partner about something. I had heard a rumor Jim was into BDSM, but gave it very little thought. (Whatever floats your boat, no skin off my nose).

Cut to last Friday. He Facebook messaged me asking if he could ask me a question. I thought it would be firm-related, so I said sure. He said nevermind. Two days later, a mutual friend (Sharon) asked if I’d be interested in entering a D/s relationship with Jim. She made the request at his behest, she said. Sharon described it as, “You let someone pamper you and you belittle them.”

I’m not into BDSM, but in my opinion that’s not the issue. This is such a breach of boundaries and professionalism that the more I think about it the angrier I get. We are not friends, we don’t interact socially, and he leaped over several levels of personal intimacy even making the request. Even though Sharon said “Nothing sexual,” to me that’s still a request for intense intimacy.

So, to the question. Do I say something to him? I interact with him professionally now and then. Do I tell him this was inappropriate, rude, and objectifying, or do I write it off and hope it never comes up again? (I told Sharon to tell him “No.”)

– I’m Not Yer “Queen”, Pal

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Dear Captain,

A few months ago, two of my mutual friends/acquaintances split apart. They were quite close and while I don’t know a lot of details, evidence indicates to me (and actually both friends confirmed) that the friendship had turned codependent and one friend decided to make a permanent split for a variety of reasons that are his and I have never attempted to pry.

They live in different cities and my interactions with them never coincide. Luckily. I see them both regularly as one is my coworker, and I have grown a lot closer to the other as we started working out and playing D&D together on a regular basis.

My question concerns the co-worker friend. It’s looking like she is viewing me as her new bestie and I am worried because her behavior is setting off a lot red flags of bad/codependent friendships I had in the past where I essentially ended up becoming someone’s therapist and taken advantage of. I have done A LOT of work in the past year identifying my own behavioral issues in these friendships and setting up firm boundaries so I don’t get cast in the role of therapist for someone again, but apparently I messed up along the way to where I am now.

I have a lot of sympathy for my co-worker friend, as I understand that losing a friend is difficult. I had also split up with my boyfriend around the same time, so I could commiserate with her and the hardship of losing someone who was a huge part of your life and moving on. However, I was not prepared for an average of 8 to 10 texts per day, seeing each other at work, facebook messages, and the what not. Communication ranges from bemoaning her loneliness, ramblings of being upset at other friend, and also random bits about her life that I think would be more appropriate for a Twitter account or a handwritten journal. Most of time I just don’t know what to do with it or how to respond. I end up getting overwhelmed by the amount of messages and feeling suffocated/exhausted.

This behavior is very new and only happened after the cut off from the other friend. I don’t want it to continue and I feel very uncomfortable around her now. I am not good with people who come off as clingy. I get frustrated, frazzled, and there are many many instances where friendships either ended or relationships never got past the 3rd date because the other party demanded more of my time and attention than I could give them. I am highly introverted, I need a lot of mental and physical space, and I really really really enjoy being alone (this includes not getting lots of texts). This is How I Do Me and while she and I have known each other for a few years, she has never really gotten to know me well enough to know this. Our friendship level has been mostly at work, rarely hanging out outside of work due to living in different city issues.

I guess my question is two-fold. 1) How do I nicely assert to her that we have very different communication/friendship styles and while I think she is lovely person she really really really needs to stop because our friendship really cannot sustain this and 2) Is there a better way to identify these situations so that I can stop them before they start? I know this one seems pretty small, but I have ended up in several very intense and dramatic friendships that all went up in flames. I don’t know how I keep getting here and it’s beyond frustrating and upsetting.

Any advice would definitely be appreciated,

I am not the bestie you are looking for.

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Dear Captain and Awkwardeers,

I have a potential freelance client, who I might do some paid work for if he can ever get around to sorting out funding and letting me know how much I would be paid for what work.

While all this is being sorted out he and I have been emailing back and forth about the topic of our professional interest. He is knowledgable though I have more knowledge about the specific project he wants to do.

I have also met him a couple of times — for coffee, in daylight, for professional business meetings.

Anyway, more recently this potential client, let’s call him Doug, has been emailing more frequently and has suggested we talk on the phone a few times about work issues. However, his conversations have mostly been about other, non work issues and he revealed that he has been tracking me on social media. Specifically, he does not have a Twitter account but he is very very familiar with everything I tweet and has brought up a couple of things in conversation as evidence that I am “stressed out” as he put it and “need to relax.”

The tweets in question were me remarking that I had blocked someone for being offensive and using profanity which I don’t like on social media. Apparently Doug read this as “she is very stressed and hurt about this big incident where a man threatened her!” when in reality I was mildly irritated and forgot about it immediately I’d told my followers I’d blocked the silly troll. Oh, and when we speak, Doug also calls me by my Twitter user name which is not a nickname I use in my personal life. (it’s a name based on an animal that sort of sounds like my actual very common name)

Another time he asked me if I had “relaxed” at the weekend because I tweeted I was going to watch a play after a very hectic work week with lots of tough deadlines.

My Twitter is open, it’s a mix of personal and professional stuff as I have developed a group of followers who are interested in my life. So it’s open for him to read. But as Doug keeps insisting, he has not got an account himself so it’s not like I am one of the folks he’s following. I find it creepy that he is reading everything I write there and commenting on it, that he calls me by my user name  and the fact that he tells me about it makes me feel surveilled. He never ever comments on the professional stuff, which I would have found totally fine. It’s always the personal stuff and he always reinterprets it through this “poor little stressed lady” lens.

This weird feeling crept into our last  physical meeting, he shook my hand by taking my hand in both of his and sort of pressing it and then he said “bye, bye, sweetheart” which is not how people in my profession behave here. Things are “formal friendly” but you don’t call women this stuff AT ALL EVER.

This dude is my age by the way. 

Am I over reacting to find this creepy-ish? It’s like Doug wants to go over a line of being professional and be my friend but we just don’t have that background. Am I over reacting if I don’t want him as a client? Maybe he is just being friendly and he is a bit awkward around women (my profession is almost totally male dominated and quite macho) but I feel really weird about it all.

Slightly Creeped Out

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Oh Captain My Captain:

I’m running into a communications problem, and could use some advice.

First the backstory: I live with my parents. My mother, who is nearing seventy, is having arthritis issues and needs a little bit of extra help around the house; generally more help that I can reasonably provide while being a full-time student. A year ago, a friend of mine had to choose between an abusive situation and homelessness, and I convinced Mom that we could offer her a third option. Now we have Kat in our guest room, doing dishes and minor housecleaning tasks for ten dollars a day plus room and board.

Now, the problem: Mom is unhappy with Kat’s performance. A lot of this is coming from the fact that Mom isn’t actually talking to her. She doesn’t remind either of us of routine tasks (because we’re intelligent people and she shouldn’t have to explain the obvious), and deals with extraordinary requests by telling me that they need to be done (with the unspoken riders of “so get Kat to do it” and “you should already know how I want that task performed” and “I will be Very Upset if you do this yourself instead of making sure Kat does it to my specifications.”) When, somehwere along the line, communication inevitably breaks down and something *doesn’t* meet with her approval, I get to listen to Mom rant about how she’s not getting what she’s paying for and how Kat isn’t ever going to be able to make it in the real world if she can’t complete simple tasks. Mom does not, generally speaking, ever voice concerns directly to Kat.

Do you have advice/scripts/etc. for how to stop being the Mom-to-Kat translator in this arrangement?


The Messenger Is Tired Of Being Shot

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Hi Captain,

I’m a twenty something female working in a retail job where it’s NECESSARY to work as a team. In the six months I’ve been at my job, I’ve built especially great rapport with a few people. The man henceforth named Paul is one of them. Paul is a year younger than me. Most of our dynamic has been sarcastic banter, punctuated by some more serious conversations about a wide variety of topics. After about two months Paul asked some questions about my opinions on romance related topics (we were off the clock and out in a group with coworkers), and I answered in the context of the happy/trusting/loving relationship I have with my boyfriend of 4 years. Paul seemed surprised to hear about him.

I later brought up one of Paul’s questions I didn’t feel I answered well, and he got extremely flustered and changed the topic. A week later he told me that he struggled with feelings for a coworker at an old job for a year or so before he really stopped having feelings for her, and he regrets that it took him that long to deal with an unrequited crush. Since he told me about that, he hasn’t brought up anything even remotely related to romance.

I’m pretty damn sure that Paul has a crush on me. He hasn’t said or done anything inappropriate either in or outside the workplace, and since describing that old crush has not brought up romance in any context (that was nearly 3 months ago). It doesn’t get in the way of our work, most of the time we still execute the sarcastic banter/serious topics conversations without a hitch.

But I definitely feel like there’s a weird feelings stalemate. In my personal life I would have confronted him about it long ago and let him know that if he can’t handle being around me, then he shouldn’t be around me, and I’d be happy to have his friendship whenever it’s just friendship. But given that we work together that’s not an option, and I don’t know what’s appropriate. I feel bad because I get the sense that he’s doing everything he can to keep the feelings off my radar since that story. If he were creepy I’d tell a manager, and if the fact that we get along didn’t make our job way easier and more enjoyable it would be an unwelcome but simple task to freeze him out. Ultimately I just want to be able to work and occasionally hang out with this guy in group settings without the sense that he’s experiencing heartwrenching crush feels half the time I laugh at his jokes. Is there even anything to do, Captain?

-Midshipman Awkward Sauce

Dear Midshipman!


You’re an empathetic person, so you are putting yourself in his shoes and wanting to make things better, but you can’t fix this for him. Short answer: Say nothing, it will get better soon. “Paul” is actually handling all of this very well, in my opinion, and it would be a mistake to stage-manage his feelings or pry further into them.

He most likely did have a crush on you, he figured out that it would not be requited, and he bailed out just in time before telling you about it beyond an oblique reference to a past situation. Of course he feels awkward, he’s got all these feelings and he can see how very close he came to 1) asking out a coworker and 2) macking on someone who he knows is happily coupled up. I think it speaks to him being a good person that he pulled back when he did. You can help everything get less awkward by being your same basic amount of work-friendly to him and letting him save face. In my opinion, he won’t thank you for addressing it directly: Imagine someone else peeling off a scab that’s on your body, and that’s pretty much what it will feel like for him if you bring it up before he does.

For now, return the text of your interactions to normal relations, ignore all subtext unless it does get angry or creepy or unless he sheepishly confesses, “I was developing a crush on you and that’s why I’ve been acting kinda weird lately” at which point you say “Aw,  knew *something* was up, but I didn’t want to make you more uncomfortable. So you know, I really like working with you and I’d like us to be friends, and I’ll follow your lead on that.” 

Hello Captain Awkward!

I love your blog. I love it so much that I’ve read through your archives and found a few questions that are cousins to, but not quite the same as mine, so here goes:

I am in my mid twenties and work at a nonprofit in a large, diverse (racially/ethnically, economically, politically) city. My organization trains and places volunteers to tutor children in Title I elementary schools. All of our volunteers are hardworking people who are very generous with their time and resources. Most of our volunteers are kind and thoughtful about the challenges many of our students face, and about the differences that may exist between their backgrounds and their students’ backgrounds. Some are not.

Some people say terrible things, usually privately to staff (if volunteers say racist things to students, we ALWAYS step in. It also doesn’t happen too frequently, thank goodness. The questions is more about one-on-one interactions with staff members.)

“I like working with Joe. At least he has a brain in his head, unlike Rose.” [not their real names]

“When I went to Ethiopia I expected to feel sorry for them, but I just felt like ‘get up off ground, stop pissing in the street, and clean up your city!'” [many of our students are Ethiopian]

“So are these poor kids?”

“It’s just too bad his parents don’t really care about his education.” [not true]

“I just don’t feel comfortable in this neighborhood. You know, since I’m a white lady.” [yes, someone said this]

There are semi-frequently comments from volunteers assuming that of course our students don’t have fathers in their lives, how their parents probably don’t care about how they’re doing in school, and how their students must have a terrible home life. Of course, some of our students may be in these circumstances – the problem is jumping to these conclusions after having spent 0-5 minutes with a student.

The comments range from foot-in-mouth to super racist, and those of us on staff struggle to know how to handle them. Some complicating factors:

1. In a perfect world, we’d have so many volunteers that we could dismiss the racist ones and replace them. Unfortunately, we need every volunteer we’ve got, and usually these volunteers are at least capable of not spewing this stuff in front of students, which is really the only way to get rid of a volunteer.

2. Part of the organization’s mission is to help educate people who don’t know much about urban education so they can become better advocates for our students and their schools. Therefore, though our first priority is our students, our second priority is providing excellent “customer service” to our volunteers.

3. Most of the offending volunteers are white, wealthy, and middle-aged/seniors who have raised children. The staff is in their 20-30s, mostly not white, definitely not wealthy, mostly childless.

Most of your scripts for dealing with racist behavior tends toward the more confrontational side. Though often wish I could employ them, I’m not in a position where I can straight up tell people that they are being racist. Do you have some scripts to help us make it clear to volunteers that certain comments are not acceptable, while still maintaining a good working relationship? Or do we have to pick between standing up to racist comments and making sure volunteers stick around?

Thank you for your help! I know this is a little long, so feel free to edit as needed.

Please Don’t Volunteer Like That

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Oh my Captain!

I’m working at a temp data entry job, where I scan and index files prepared by another team. When I started this project, the supervisor told me to go to her if I had any questions, or noticed anything unusual. I’ve been doing that, and I’ve been catching a fair few errors. After about a month of this, the supervisor decided to point a couple of the more common errors out to the prep team, so they can avoid them.

When this was pointed out to them, they seemed wounded, said they were shocked to find out there had been mistakes, and said I should bring questions to them first, so they can correct them.

I’ve been trying that for the past few days, but it’s been going… weirdly…  Here’s an example.

I have three files, one each for Alice, Bob, and Carol. They put all three under Bob’s name. When I point this out, the prep team said that all three shared Bob’s ID number. This is incorrect. I know they know it’s incorrect, because they use the correct ID numbers elsewhere in the file.
I’m inclined to go back to just asking my supervisor, but I’m worried that the prep team will take offense again. If they wanted to, they could make my job really difficult. I feel like they don’t take anything I catch seriously, possibly because I’m considerably younger, female, and a temp.

Thanks for looking this over,

Not Trying to Make Trouble

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