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Overthinking It

Hello Captain!

Here’s a few things about me to help you understand my story. I am 23, a virgin, and have never had a romantic relationship with a man besides a date.

A few weeks ago I recently went for a night out drinking with three guys that I work with. One of whom, Greg, I invited along because I’ve had a slowly developing crush on him for the past few months and wanted to hang out with him outside work. The night was fun, but took a different turn than I expected once Greg started getting really drunk. We’d flirted earlier in the night, but once he was drunk he started hitting on another girl, clearly hoping to go home with her. She ended up leaving and when I approached him to say he should get home he asked me if I would go with him and sleep with him. I told him no because he was really drunk, but said I would give him a ride home. On the way he started talking about how it’s better to remain closed off because he’s opened up in relationships and put in a ton of effort and only gotten hurt, but wasn’t sure why he was telling me this because nothing would come of it. When we got to his house he invited me in and we talked for a while before we kissed. We started making out eventually and he asked me to spend the night. I did, but we didn’t have sex. The next morning was awkward, neither one of us saying much, and we agreed to just see each other at work.

The following week we had a discussion about it at his place and he said he didn’t want a relationship. I told him I’d like to get to know him better and to try to be friends and he agreed. We spent the night talking and watching movies and I slept over again, though nothing physical happened. A few days later he sent me a flirty text and we spent the night flirting, agreeing to meet up again. I went over later in the week and we talked, watched movies, made out (I initiated it), and played chess until 5 in the morning and I spent the night again.

This last week we’ve had conversations via text about personal things, getting to know each other. A few days ago we had another work outing at a bar and each of us said how it was a possibility we would go home together again. As we left the bar he texted me to say I should come over if I wanted, so I did. At his place he shared personal things with me and eventually we went to his room. We almost had sex, but I stopped it. He respected my decision, but I think he was upset and we did other stuff (which I enjoyed) without actually having sex. I wanted to have sex with him, but wasn’t sure if I should because we’re not dating and he doesn’t want to date me. He said he hasn’t fooled around with anyone besides me in a year and half, but said that we’re not exclusive, which definitely bothers me.

When I asked him what he would call us he said that we’re friends and that he is someone I can talk to about anything I want if I need to. He did however say that he doesn’t form emotional connections, which is confusing because it seems like that’s what we’ve been doing. I am a major overthinker, something he knows and has been trying to help me with. I struggle with opening up to him because I’m afraid of what he’ll think and he has been really great with trying to let me know I can share things about myself with him. He’s been very open with me.

We’ve left things saying that we’d like to keep doing what we’re doing because it’s fun and he told me I “shouldn’t ruin a good thing with my overthinking.” I want to enjoy this without obsessing about it too much, but I’m not sure how. My questions are:

Should I just relax and enjoy this despite the fact I want it to be something more?
Does Greg seem like a good guy?

Thank you for reading!

Sincerely,
Confused Overthinker

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The Goat Lady, who sorts my inbox, kindly created a tag called “low intensity” for questions such as these.

Dear Captain,

I am in a fairly recent relationship with a wonderful man I’ve been infatuated with for years (…on and off – we weren’t Firthing!). When we first started dating, I was nervous about a whole host of potential pitfalls (long distance, exes, contracting Oneitis) that delightfully turned out to be illusory, and at this point, we’re comfortable with each other, communicate regularly and openly, and have a lot of fun together.

So, my question is this:

While we’ve been friends for years, this isn’t a BEST Friends Fall in Love Story, and I’m sometimes surprised by how different it is to talk with him than with most of my close friends. Other than the boyfriend, the kinds of friends I stay up all night with are huge readers and unabashed lovers of pop culture, and we love nothing more than to conduct elaborate feminist critiques of Game of Thrones or debate the literary merits of fanfiction. I don’t expect (or want!) my boyfriend and I to like all the same things, and I know we’re still in the process of figuring out what we like to talk about when the “how was your day”s are done. And to be fair, he’s offered some pretty interesting feminist critique of Game of Thrones himself, but such discussions don’t seem to fascinate him in the way that I’m used to, with each of us tumbling out thoughts faster than we can speak and getting caught up in the joy of endless critical analysis. So even when we DO like the same things, I don’t know that we like to talk about them in the same way.

Since there’s the whole “I’ve been infatuated with him for years” thing going on, I can’t tell if this is something we’ll probably get past as we recognize not just the WHATs but the WAYs we like to talk about things, or if it’s a bigger problem of mismatched perspectives and ways of engaging that I’m choosing to ignore because LOVE.

How important is a similar conversational dynamic to happy, healthy relationships? I am currently very happy and in love, and I love that we have comfortable silences as well as witty repartee, but I’m constantly taken aback when conversations I expect to last ages seem over quite suddenly and would love to hear your thoughts on the role this plays in life/love/etc.

Thank you,
Not Awkward, Still Silence

Dear Not Awkward,

I don’t know what to tell you. Some possible explanations for what you are experiencing:

1) Your Jerkbrain, unused to contentment, is looking for something to worry about and has decided that this is it.

2) The years-long fantasy of this dude was better/more interesting than the reality of life with this dude, who is kind of boring when you get right down to it.

3) In long-distance relationships you can’t really coast on proximity, so the quality/quantity of conversation is looming larger as a factor as you try to find an equilibrium.

Since things are good, why not keep enjoying yourself and let time sort it out?

Hi, Captain!

Not a huge crisis, but I wonder about your perspective on an etiquette issue.

I have a lovely set of in-laws who are chronically, perpetually, and often extremely late. This is a huge pet peeve of mine, as I see arriving promptly to be a matter of respect, and I function exponentially better when my life is carefully scheduled. This is annoying enough when they are late on me. But my question is when we have a plan as a group and there is a danger of them making me late.

We have a family event coming up soon, where my husband and I will be staying with them for a period and attending a series of events in their company. I dread the idea of arriving continually ten minutes, thirty minutes, an hour late to the people who are expecting us, and to events I am looking forward to. I worry that being too insistent on timetables and getting after them too much to keep moving will make them think I’m a nag, or too controlling. Do you think it would be okay if, when the appointed time to leave has past, I cheerfully tell them that Husband and I are heading out and will meet them there when they arrive? Or do you have a better idea to keep to a respectable time table without coming off as rude or inflexible?

Thanks!

- Early bird

Dear Early Bird,

You nailed it when you suggested that you and your husband should make your own way to these events. Treat that like it’s Plan A, not a sacrifice you are making because of their lateness. Only mention your plans when you have your coats on, your keys in your hand, and are heading out the door – you’re informing them of the plan, not discussing or negotiating it. If you need some handy excuses, try: “We want to get there early/make a stop on the way/we might want to stay longer/leave sooner than you/we’d just rather take separate cars, thanks” and keep your tone friendly and light as you glide out the door.

Everyone in their extended family knows exactly how they are, you know how they are, your husband knows how they are, and I’m pretty sure they know how they are. They are of an age to have raised an adult child and are not suddenly going to change their habits. This is one of those times where you have the chance to just do what you need to do with the least amount of friction possible, so take the easy way!

Moderation Note: Thread closed. Turns out that my budget of fucks for reading contentious, self-righteous discussions about lateness and rudeness = zero fucks. 

Dear Captain,

I’m a recent college graduate and was interviewed yesterday on national TV about the field I’ve started working in. The other people on the panel were way more experienced than I, and some of them are are moderately famous. The program wanted a young voice/perspective, and I was so honored to be asked to do the kind of TV appearance a more senior colleague would normally do. I was also a little terrified and worked really hard to prepare.

The interview went great, and I left the studio walking on air. I felt I came across as confident and informed and that I had represented my employer, my field, and my generation (corny as it sounds) extremely well. I’ve never been so proud.

Then the interview aired and I stared horrified at my screen as my eyes narrowed in on the noticeable sweat marks under my arms. I can’t help but feel that what should have been such a professional joy is ruined by… armpit sweat. I feel so stupid for wearing a color that really showed it. Rookie wardrobe mistake. Rookie, sweat-inducing nerves.

The interview aired at a time most people I know were at work, but it can be streamed online starting today. Now I have a long list of proud friends, family, and former professors/mentors who are expecting a link to the online clip. My grad school program wants to share it on their social media account. I’m so embarrassed at the idea of all these people seeing it. I didn’t tell my parents I would be interviewed, because I wanted to surprise them with a link to the clip in clever email (note to self: not everything has to be clever). Now I’m just dreading my mother’s comments about what a shame it is I didn’t wear a darker color. Surely I’m not the first person this has happened to, but I also can’t recall having ever seen armpit sweat on TV, so part of me is also convinced that this was a uniquely stupid thing to let happen.

I’m also beating myself up for being so obsessed with my appearance and not able to get past it to be proud of my ideas and composure. Am I making a mountain out of a molehill? How can I convince myself that my professional awesomeness trumps my sweatiness? How can I get past the feeling that the interview is ruined or somehow embarrassing and send it to friends and with pride?

Smart and Sweaty

Dear Smart & Sweaty,

The interview is done, and the clip is out on the internet now, and it can’t be undone or taken back. I haven’t seen it, so I can’t make reassuring “it’s not that bad!” noises your way, but I suggest that you show it to a trusted friend or mentor without mentioning the stains and see what they say. We all search our own appearances for flaws in a way that most other people do not.

I think you should share it and encourage others to share it without commenting on the stains at all and focus only on the content of the work. If anyone brings up the stains, a) that’s a pretty weird, rude thing for them to do, and b) I think you will feel much better if you find a way to play it off if it happens. “Wow, thanks for noticing! I was worried no one had.” “Would you call it a stain, or more of a river?” “Next time I’m going to wear that old bridesmaid’s dress, so that the stains really pop against the seafoam organza!’ “Yeah, thanks for pointing that out, Mom.” 

You have nothing to apologize for. You didn’t know it would happen. Your words were still your words. TV lights are hot. Sweat happens, you are a human being with glands. People who go on camera for a living have teams of paid professionals helping them look perfect. I feel gross for linking to this listicle on Celebrity Sweat Incidents especially since the tone is “they should take better care of this issue,” but I want you to have some visual aids that show that even people with tons of camera experience and teams of staff devoted to how they look are human and have glands. I also found this media training PDF for how to prepare yourself for a TV appearance from the University of New Haven that has, literally 100 separate tips for how to look and behave during a TV interview. I don’t want to panic you further by making you memorize 100 new things you should have done, but the takeaway is: Being comfortable on camera is complex and there is a learning curve to doing it.

Please stop beating yourself up! I suggest that you do some more TV appearances as soon as humanly possible. The more you appear on camera, the better you will get at it, the more variety of clips there will be, and the more you will become recognized as an authority who can handle themselves on camera. Please do not let this one quirk of biology shame you out of the excellent career you just beginning.

Dear Captain Awkward,

So yes, this is a happy problem. You’ve written well on work matters in the past, so I’m hoping you can help with this.

I have spent a few years in a frustrating job/environment, but started an excellent new job about three months ago. I am now a senior manager, with only two people above me in my specialism – the Exec Director, and the Deputy Director who is my line manager.

The job has been full on from the start, but I’m really enjoying the new opportunities and the trust, and as far as I can tell I’ve done well so far.

However, I just found something out which has thrown me slightly.

I thought I was one of four equal senior managers, with the others having more time in post. But this turns out not to be the case. Both of the Directors have told me that I am third in command, and that they appointed me with the intention of grooming me for the Deputy Director job in a few years. I can have (nearly) any training I want.

Woohoo, yes? And part of me really wants it, but part of me is petrified with the fear of failure. I am a nerdy/dorky/socially awkward woman – (still with substantial privilege, cis and white, and I read as upper middle class despite having grown up very poor). I have worked hard on the social awkwardness but it is still A Thing, and I have low confidence in my ability to be socially smooth. And the previous frustrating job has knocked my work confidence.

Social smoothness, and leadership skills, negotiation and influencing, and change management and all that stuff, are more and more important in the senior jobs. That’s what I need to learn in the next few years.

But how? I can do the technical part of my job, and standard line management, but….?

I am pleased they see potential in me, but I don’t see it myself. How do I avoid holding myself back?

How do I learn something so nebulous? How do I know if I’m getting better at them? How do I learn to get over my awkwardness and my assumptions that I am crap at these things? How do I develop a model of myself as a (nerdy, female) leader?

I don’t even have the tools to start to learn, or know what to look for in myself.

Please help!

Signed,
Not A Leader

Dear Not A Leader,

You’re familiar with Impostor Syndrome and the Dunning-Kruger Effect? Good.

Your mentors have offered you training, which is wonderful, because it demonstrates that:

1) They don’t expect you to already be an expert in leadership/communications/management, etc.

2) They recognize that these are important skills unto themselves in addition to the technical competencies you possess.

3) They are building in time and a budget for you to level up these skills so that you will be ready when the time comes.

In other good news, there is training out there to be had. Since I don’t know exactly where you are, I did a Google search on “professional communications management training” to give you an idea of what kinds of things might be available.

You could study online (though I think you might find this very basic).

Harvard University has a ton of continuing education-type courses and seminars in the very subjects you want to learn, with titles like “Advanced Executive Communication Skills,” “Communicating With Influence: The Art of Persuasion,” “Cultural Competence for the Global Workplace,” etc. What’s the fanciest pantsiest business school closest to you, and do they offer such things? There’s no reason not to make this both a learning and a professional networking experience and get something shiny for your resume. There are tons of non-university affiliated training organizations that do this sort of thing, too, at every intensity and budget level. In addition, you could ask your mentors if they’ve ever taken courses that they think were particularly helpful in developing their management skills.

Conclusion: You’ve got this and you’re going to do great. This also seems like a good idea to watch & read a lot of epic sci-fi and fantasy stories where humble people who are convinced that they are not leaders become leaders.

 

 

 

 

 

 

 

 

 

 

 

 

 

Hi Captain,

I am a single man who, after the end of my last relationship, took a
few years out of the dating scene to really rethink what I want out of
my love life and learn to be happy with myself. (For context, I’m 32,
my divorce was 5 years ago.) I feel ready to come back onto the
market, but I’m finding it hard to meet single women who actually
inspire my interest. I’ve tried online dating and singles events, but
they don’t really work for me.

Far from sitting idle, I have become more and more active in the past
couple of years about pursuing my hobbies and interests, which has
helped me extensively expand my social circle. However, it seems that
every time the circle grows, the women I meet are either happily
attached, gay, or just folk I’d rather have as platonic friends than
romantic partners. I’m thrilled to make all these great new friends,
of course, but there’s more I want out of life than my platonic
friends can give me.

Cutting back on my hobbies and going to more singles events would be a
false economy; I’m at least making new friends through hobby events,
whereas singles events have given me nothing. At the same time, I
don’t have time to cram in even more regular social activities – not
without ending up with such a busy schedule of commitments and
responsibilities that there isn’t actually space for a relationship in
my life anyway.

This being the case, I’m thinking about outsourcing the problem by
asking trusted friends to try and introduce me to single friends of
theirs. Since I’ve put in the work to expand my social world in the
first place, why not enjoy the benefits of that expansion? Plus I’d be
more confident making contact with someone a friend has recommended
than a total stranger.

That said, how do I:
- broach the subject in a way which makes it clear that this is a
serious request I am making of my friends without sounding needy and
pathetic?
- make it clear that if people don’t want to play Cupid for me we’re still cool?
- make the point that I’m not up for “blind dates”? (I’d like to know
a bit about the person in question before meeting them so I can
politely decline suggested matches which clearly aren’t going to
work.)

Yours,

The Last Turkey In the Shop, UK

Dear Turkey:

I have thoughts! on your question.

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Hello Awkwardeers,

I recently got back in touch online with an old friend who I am genuinely excited to be reconnecting with after more than a decade. I knew him when we were both in our late teens. He was fun to be around, but a mutual (male) friend described him as “needy.” I was glad to hear that this characteristic of his was not just in my head, and that he made this impression on men too. He had this way of making you feel really bad when you said no to him; it’s not that he would pressure you, exactly, but his disappointment would become this entity that lived in the air between you and him. I don’t know how else to describe it. Despite this quirk we were good friends; he obviously had a thing for me, but he was one of those dudes who obviously had a thing for all of his female friends. (I should mention that he never used the Disappointment Monster to try to get sex; he was more of a generic attention vacuum.)

Through Facebook I know that he is now openly poly and involved in kink and tantric sex communities and that sex is very important to him. And that is great! I don’t think people should feel bad about being open about their sexuality! But.

As we’ve been reconnecting, we’ve done a bunch of discussing what is going on in our lives, and he brings up sex, briefly, all the time. Like, the list of what he’s been up to lately is sex and work and hobby X. I tend to just ignore it (“hobby X? I love hobby X! Let’s talk so much about hobby X!”), but it still makes me vaguely uncomfortable; I’m significantly more private about my sexuality. I can’t tell whether it would make me uncomfortable if anyone were to work sex into every conversation, or if it specifically has to do with the Disappointment Monster and his history of wanting more from me, or both. I think to him, sex is not only something that he likes to do / talk about, but a big part of his identity in a way that it isn’t for me. I’d feel bad telling a friend not to talk to me about their (non-sexual) interests, and of course I wouldn’t ask a friend who was a sexual minority to “stop shoving their sexuality in my face.” (I realize that the situations are not exactly analogous, but I worry that essentially that’s the kind of bigoted request I’d be making if I tried to set some sort of boundary in this area.) He isn’t pressuring me for anything– we don’t even live in the same city. The thought of asking him to stop makes me feel hypocritical and sex-negative, but I can’t deny that I’d prefer he stop. Should I try to get over this, or ask him to change?

Sex Neutron

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Dear Captain Awkward,

So, I’m turning 30, and I don’t know how to interact with people. I think it’s because I’ve had OCD from at least the age of 9—real OCD, with repugnant obsessions about incest and such, not “I color coordinate my sock drawer”—and like a lot of people I kept it a secret. And I had panic disorder, which made me agoraphobic. Also, starting around 12 I felt like I was constantly stuck behind a pane of glass, which according to Wiki might mean I was dissociating, but whatever you call it, it was unpleasant. So to sum up, all the important things in my life were a horrible dark secret, other people didn’t seem real, and I basically couldn’t leave the house without fearing I’d have a panic attack, and frequently having one. It was not conducive to making friends.

In college I was lucky enough to make one super good friend—entirely through her initiative—and several good-ish friends. And then senior year I had a nervous breakdown and scraped through graduation and had more nervous breakdown and went on drugs and into CBT. That was six years ago and I’m much better now. But I don’t know how to deal with people. I didn’t realize this before, because I never wanted to deal with people—I thought I was just introverted and misanthropic, and I liked being that way. Now I don’t know what I am. I don’t think I’m shy. In a crowd I’m not nervous; I’m just nonplussed, like if you walked up and randomly gave me a lathe: I’m like, “Wtf is this for?” I still automatically say no to all social invitations, because even though, so far, I haven’t had real panic attacks on the drugs—and hopefully never will again, knock on wood—my instinct is still to stay home all the time. To my mind you have to have a really, really good reason before you leave the house. And people make me tired. When I have to associate with people, e.g. at work, they apparently like me, and I generally like them; but when getting together is optional, I just… don’t. But I’m lonely.

Romance is particularly a problem; or at least, it’s the problem I mind most acutely. I’d ruled out ever having sex till a few years ago, because repugnant obsessions. (Use your imagination.) Now that I’m better it seems like a possibility, but I feel… well, warped, I guess, like I missed some formative experience and it’s too late for me to be fixed. But dammit, I’d like to have sex, and not just sex, but a relationship. I get filled with hopeless romantic longing on a predictable monthly basis and also any time I see Robert Downey Jr. All my friends are married. I want that shit. But again, I’m almost 30; I don’t have time to replicate all the socializing experiences I should have had when I was 8. What the hell do I do with this lathe?

More Awkward Than You Are

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Every month we answer the things people typed into search engines like they are actual questions, adding punctuation but leaving the wording intact. If it sounds like me saying “but you could just not” 20 times in a row, that’s pretty much what happens every month with these. Enjoy?

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