Captain Awkward’s Dating Guide for Geeks

The post title was the subject of the email exactly as it came to my inbox. That will be important later.

Hey there Captain,

I recently moved to a job that not only frees up more time to focus on schooling, but pays better. On the last day at my previous job, a girl I’d occasionally worked with and spoken with in the breakroom, asked for my number.

If her interest wasn’t obvious enough, as I walked out the door for the final time, her question was whether I had a girlfriend. I told her no, and to my amusement, her reply was that she’d text me. Needless to say, I got a text bright and early the next morning and we’ve been texting a bit.

She’s nice and I get along well with her, but I’m unsure about making the choice to date her. There are a few things I see as obstacles, but can be worked through.

She’s the daughter of my previous manager. Introductions as a boyfriend would be awkward because my manager didn’t want me to leave. I worked hard, kept a positive outlook, and somehow managed to get along with even the prickly people there. I lit up many people in that glum environment.

While texting, she obviously wanted to get to know me better, so I took the lead, organized a meetup, and we had fun, went for coffee, and wandered around the mall.

It was a great chance to get a feel for her personality, lifestyle, relationships, and maturity. When I asked her what she enjoys doing, she said that she didn’t really have any hobbies, but that she enjoys hanging out.

During the meetup, she spoke mostly about how she doesn’t like work, her parents are always mad at her, her exes (about two or three by how she spoke about them), and her life in general. After the meetup, she told me she had fun and wants to meetup again next week (the next free day she has).

Clearly she enjoyed my company if she already wants to hang out again. I asked what she wanted to do, and she said “I don’t know, I’m good with anything”. This bothered me somewhat, but I’m a big boy, not everyone knows how to be assertive.

When I asked whether she’s doing post-secondary, her answer was the generic “I hated school, so maybe I’ll become a cosmetician”. She agrees with whatever I say and doesn’t have a lot to say about her day, goals, or hobbies. That bothered me more deeply. I’m easygoing, so I spent time reflecting on why this information bothered me.

I have my life together. I’ve got a great part-time job to cover costs, university and my budget balances at the end of the day. I pursue hobbies such as photography, programming, hiking, and cooking. I’m on great terms with my family. I know myself well and what I want in a companion. This girl is wonderful, but it seems she dates as a form of entertainment; escape from her life. I date for a strong equal to share my interesting life with, and I’m not seeing a lot of that in her.

I’m not interested in being a crutch and I can’t save her from a boring life. If there’s a way for her to grow up and not rely on me to fill up her open schedule, I’m open to sharing a life with her. Although she’s my age (19), I don’t think she’s at the point where I can tell her this without grievously wounding her undeveloped ego, especially given how she admires me.

My first relationship (a different girl), about a year ago, ended because both of us had been insecure. Since then, I worked at self-improvement, and I’ve honestly been impressed with my progress. I’m a much more confident and relaxed person than I was.

I know myself well enough to know conversation is important to me. I’d feel lonelier in a relationship than alone if the other person had nothing interesting to talk about, AKA, their own life. I’m looking for a healthy relationship where our worlds don’t revolve around each other, but where we know there’s respite in each other’s company.

How can I kindly tell her that she’s wonderful and brave, but not ready to be the female lead in my story?

Casting a Female Lead

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Dear Captain Awkward,

After a very painful marriage breakup and over 10 years of not dating (for many reasons including mental breakdown, SSRI sexual side effects and being too scared to go back into that shark pool – and yes, I’m currently in therapy) I’ve recently started online dating.

At the end of a recent (first meeting) coffee date, the man indicated that he would like to see me again, but then rang a few hours later to say that he had changed his mind. I am totally ok with him changing his mind, but the call made me feel quite uncomfortable because he seemed unable to just say what he needed to say then get off the phone. I assume he was trying to be polite, that perhaps he thought it was more chivalric than sending a text message or email or just dropping off the face of the earth, but I would actually have preferred one of the more impersonal methods in this setting, where I hardly know the man and am never going to see him again anyway.

My question is whether I should be upfront about my preferred mode of rejection while we’re still just emailing or texting, or whether it’s silly and preemptively negative to bring up how we’re going to end things before we’ve even met, and I should just learn live with the fact that all rejection will be at least a little bit painful.

Scared of the Shark Pool

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Hey Cap, ive got some girl troubles i hope you can help me out with. So a couple years ago i got the pleasure of meeting a girl, me and her would hang out almost daily and we became very close, we were extremely flirtatious and everbody thought we were together. But a few months into our friendship our communication went a little cold and we stopped talking for a little while. I then had a brief relationship with someone, and so did she. Its now a year later and we have been hanging out again and i brought up the courage to ask her out. If i would of done this when we were closest back then it would of been an instant yes i believe. But now she is really hesitant, scared of being hurt, and losing me as someone she can talk to. I want some cold truth here should i keep trying or move on?


I’m so sorry that you seem to have missed the window on this one.

You saying “Hey, I’ve always really liked you and I’m glad that we were able to get back in touch. Do you think we could give dating a shot now that we’re both single?” is brave & cool. There’s absolutely nothing wrong with saying it, and there’s nothing wrong with her hearing something like that from a good friend and needing some time to process and perhaps mentally reframe things a bit before committing one way or another. I think the smart thing for you to do now is to treat anything less than “Hell yes!” as “No, thank you” and give her some space. “I had to ask, I only want you to say yes if you feel 100% great about it, so why don’t you think about it and we’ll talk in a few days/weeks/whenever you like.” Giving her and the whole matter some space will be good self-care and good care for the person you like.

It’s also a good tactic for getting to the heart of the matter. If she does like you back, if she is just sort of processing doubts aloud because she wants to be convinced, I think it’s good for you to bow out while she comes to her own conclusions and refrain from trying to convince her. People don’t forget being asked out by their friends, phones and email work both ways, and if her answer to your question a week from now is “You know what, let’s go for it,” she knows how to find you. You being respectful of her reservations isn’t going to lose you any points if this thing is meant to be, and if it’s not meant to be bowing out gracefully is a way of assigning yourself some grace and coolness points even in the middle of something that feels sucky and awkward.

Ahoy Captain and Crew!

So I’m seeing a Dude. We’re very new; I started dating him about two months ago but one month in, I went to Spain for a month and just got back.

I like this dude. He’s handsome, smart, and seems to have his head together. The sex is great. But! There are some issues, already. He lives across the street from me. My last relationship was long-distance for five years, and I’m quite used to my independence and need a lot of space. My ideal relationship: I see him maybe once or twice a week! We have amazing sex and fun times! We also occupy ourselves with our friends and work! We get closer from there over several months naturally, as we discover more about each other and realize how much we like each other! Maybe we wind up practically living at each other’s houses, at some point!

His ideal relationship (as it seems to me): I am literally over at his place allll the time, spend the night allllll the time, and am very very intertwined with him unless he’s at work, allll the time, from the moment of meeting him on.

We’ve had some issues around this already. He asked me randomly (I think it was on our third date) when I was going to “make time for him.” (on a date, when I was literally making time for him as we spoke). I say something complementary about the décor of his apartment; he replies with a snarky comment about how if I liked it so much I’d be there more. On our second date, he said if we weren’t spending Christmas together we’d “better be spending Thanksgiving together” (I was still trying to decide between several different options for Thanksgiving, all of which were friends / family who were not him, as we’d basically just met). Later, he said he didn’t say that thing about Thanksgiving.

So I just got back from Spain. I called him when I got back, and he wanted me to come out to a bar to meet him. I didn’t want to, because I was jet lagged and had a headache (did I mention I started having chronic headaches shortly after we met? Unrelated to him—I swear). I said no to the bar, and he said “I’m coming home to see you then!” Anyway, I was headachy, jet lagged and tired, and at first I said yes (because I really did want to see him), but then thought about it and called back to ask if we could reschedule for the next day because really I just wanted to go to bed and recover from the trip. He seemed upset and hurt, and made some snarky comments about how I “seemed to have a set bedtime.” I suggested meeting up the next afternoon and he seemed irritated by the whole idea. Anyway, I guess we are meeting up tomorrow afternoon but now he seems to have some sort of feelings about that.

I want to give him a chance, but I really don’t like this pattern. The headache situation is pretty bad; I’m very worried about it and am proactively trying to address it (lots of doctor’s appointments; I’m getting health insurance next week, etc.) In this situation, I seem to have less capacity to deal with relationship demands.

I’m not sure how skewed my perception is though; I’m not sure if a). my last long-distance relationship messed up my idea of what a “healthy” relationship or getting-to-know-you pace is, or b). if my headache is basically making me unable to be in a relationship; or c). if he’s being wayyyy clingy (or more accurately, would be more comfortable if I was wayyyyy clingy) and wanting to push this relationship along faster than I’m comfortable with. My instinct says c, but I guess I just need to see what others think.

Thank you all!

You’re welcome.

Sorry for what I’m about to tell you:

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Dear Captain Awkward,

I’m currently over 2 years into a poly relationship with a wonderful person. Our policy is that we’re both free to have casual sex, and we’ll treat dating people on a case by case basis. The majority of our relationship has been long distance, but I very recently moved to live a few blocks away from them.

Partner has a friend who was also known them for as long as I have. Over the course of our relationship, they’ve grown very close. Every time I heard about Friend from Partner for the first year or so, they kept assuring me they were “just friends” and that they’d never be interested in anything more with him, even though I didn’t ask for that assurance.

Then, Partner asked me if they could do nonsexual kink things with Friend, which I was okay with. This came with more assurances that they’d never be interested in doing sexual or romantic things with him, again without me asking for them.

Early this year, Partner asked to start dating Friend. I said I wasn’t comfortable with it right then. Partner asked again a month or so later because Friend’s partner decided to open up their relationship. I said I needed to wait until I lived near Partner and see if I felt more comfortable in our relationship.

Over the summer, Friend visited Partner and they had sex, even though I told Partner I was uncomfortable with that. They apologized for being inconsiderate of my feelings, saying that it just happened. A day before I moved, Friend’s new partner referred to Partner as their “metamour” in a place where I saw and Partner brushed it off as a misunderstanding. After that, I told them I wasn’t sure I’d ever be comfortable with them dating Friend while still dating me.

It’s now been two months since I moved and while my relationship with Partner is stronger than before, I’m still not comfortable with them dating Friend. They’ve given some hints that they want to talk about this sometime soon, but they haven’t brought it up yet.

Other than this issue, I am really in love with Partner, although I still don’t feel like I’m getting enough affection (school and health issues make fixing this hard).
I don’t know how to get over Partner giving specific boundaries for their relationship with Friend and then changing them suddenly.
Thinking about this situation makes me have anxiety attacks and cry. I’m working on finding a new therapist, but it’s hard having just moved and needing to find a bunch of new doctors.

Am I being ridiculous about this whole thing? What do I do when Partner brings up the subject again?

– Too Anxious, Too Needy

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Dear Captain Awkward,

I began dating someone in August even though we both knew we were moving to different cities at the end of the month. August was great, I learned more about what I want in a relationship, and we left on good terms.

This person was in my new city recently (in early October), and we resumed our “relationship” for the week he was here, but I said that after he left I wanted to stop communicating for 2 months so I could concentrate on my new city and get over him. He agreed and said that was fine.

Which brings me to today. This person and I have begun the “2 months of no communication” that I requested. It has been about a week and I just received this message from him:

“I know we are not supposed to communicate but I was thinking about the mean comment I said the other day. It was dumb and hurtful. I am sorry, I was stupid, you re sweet.”

So here is the incident where the mean comment occurred:

While we were together in my new city, we met some friends for brunch. I mentioned that the previous night he and I didn’t go to a certain concert/club because we weren’t dressed up enough. He said something like “Yea we can’t go dressed like shit. I mean, can you get in dressed like that?” and he gestured at me. I can’t remember his exact words but he basically proclaimed that I was dressed like shit in front of friends. I completely froze. He could tell something was wrong so after we left the restaurant he asked me what it was and I told him. He said I was right, that was fucked up, and he is sorry.

And now he is saying sorry again. I appreciate this, but the problem is it feels like “sorry” is not enough.

So my question is, how do I respond to this? This is a person I enjoyed getting to know, who I felt a connection to, and who I hope I can have a friendship with. Here are two drafts I came up with:

1. Thanks for saying this.

2. I’ve been thinking about it too. And a lot of other things. The past, patterns I get into with people. Maybe you can help me answer some of my questions sometime. For now, let’s stick to the 2 months thing.

Do you have any suggestions or insight? Your scripts always seem so mature and brilliant. I think, ”Obviously! That’s what you should say! Why didn’t I think of that!”

Thank you so much! I love your blog.



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Dear Captain,

I recently started dating a guy I really like. He’s a techie and most of his friends are friends from work. They do a lot of social stuff together. He’s been great about introducing me to them and inviting me to things like happy hours, which is important to me after having dated two guys who pretty much refused to introduce me to anyone else they knew for Reasons They Could Certainly Justify.

So, that’s great, right? Except hanging out with them is quickly becoming excruciating. I am not a shy person and am a pretty good conversationalist – hell, my JOB is making people feel comfortable and welcome and I spend a lot of time having dinners with people in my industry where I’m pretty much there to hear them talk about work and convincingly feign being fascinated.

What will happen is that he’ll extend an invitation, I’ll accept, and then I’ll spend anywhere from 1 to 5 hours staring at my plate or glass of wine while they talk about work. Constantly. Nonstop. If it’s not the highly technical details of whatever program they’re working on now, it’s dissecting everyone else they work with. I’ve tried gently steering the conversation towards not-work topics and contributing where I can (limited, because 1. I don’t know the people they’re referencing and 2. I don’t work in the tech field) and I’ve not been successful.

After the last outing, I asked him if hanging out with his friends = all work talk all the time? And he seems vaguely apologetic but also like yeah, this is how it is and will always be.

So. He’s spent time with my friends, most of whom are not people I work with, and we’re all able to have lively conversations about things we’re all interested in – not rehashing all the inside jokes from the last tech convention that only those who attended would get.

Applying the Sheelzebub Principle, if I have to put up with this for a few more months, much less 5 years, I will lose my mind. But I do like this guy and I want to give this a chance (I have been known to hit the eject button on new relationships very quickly in the past).

Thoughts? It’s important to me to be on good terms with his friends, even if I’m not interested in making them my friends, and he does a lot – a LOT – of socializing with them. I’m hesitant to bring this up with him because it will make me feel like that Whiny Girlfriend Who Doesn’t Understand Coding and wants everyone to dumb things down for her sake, which is not the case, and I also get that he does not control their behavior (although he certainly isn’t helping things when we’re in this situation, because he’ll sit there and do the All Work All The Time Channel too).

I get that some of these people probably are used to not having others understand what they’re talking about, and there is a fair amount of on-the-spectrum-y, social awkwardness going on here, but I come from a family of peeps with autism and actually worked in the engineering field for a while, so I consider myself pretty good at empathizing and interacting with people who might, for certain reasons, be a little wrapped up in explaining to you how the widget works, even if you’ve no interest.

– It’s Ok to Talk To Me Even if I’m Not a Programmer

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