Overthinking It

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,

I am a (female) musician just starting out on a new duo project with a fellow (male) musician, and we’re just about heading for our first gigs and things. We’re both really excited — we get on well musically and personally, and we’re enjoying what we do and looking forward to sharing it with people. However, he has a girlfriend, who is (perhaps inevitably) insecure in one way or another about him playing music with “pretty young women” (she’s a fair bit older than us two, hence the inclusion of “young”). They have their own conversations to have about all sorts of things (not my business, of course), but the nub of it is that it makes him uncomfortable having to tell her about this new duo with me. He and I are both on the autistic spectrum, and established in a beautifully blunt moment that neither of us was interested in the other for the sake of getting the conversation out of the way, and he’s since referred to me as a “top bloke”, which to me makes the distinction perfectly clear. While it’s that simple for us, it’s not that simple for her, and I totally see where she’s coming from having been in her position previously.

My question is what can I do to help the situation? He said he will talk to her about the duo at some point soon when he can find a good moment (they live quite far away from each other so it’s not 100% simple), but in the mean time, it means that I can’t get excited in public too much about it because he thinks she shouldn’t find out from me or by seeing a random Facebook post (far from unreasonable). He’s already asked me not to tag him in posts about being excited about making music together for her sake, and while I can see that it’s a small gesture towards keeping things OK from his side (he’s my friend, why the hell shouldn’t I?), I worry that I’m going to do or say something stupid that’s going to cause problems for them or for us. He says it’s not going to get in the way of the duo working and being successful, but I can’t help feeling there’s an inevitable sticking point if his girlfriend is uncomfortable with him hanging around with me at the close quarters necessary to work in such a small ensemble. I haven’t met her yet, though our paths are due to cross in the coming months, but I’m nervous of making some mistake that means that her insecurities come out and cause problems.

In short, I play music with a guy in whom I’m not remotely romantically interested, but I think my being female and apparently not bad looking (who am I to judge?) might cause a problem, and I want to know what I can do to avoid sticking my boot in it. She sounds nice, and they are basically happy, and he and I are very happy with the music we make, and I don’t want it to get any more complex than that.

Over-Optimistic Aspie Musician

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Hi Team Awkward

After a couple of years, my sister ‘Kate’ is sadly divorcing her husband ‘Adam’. This is sad and difficult for them both, but ultimately she realised she was no longer in love with him because she still has feelings for an ex (a total Darth unfortunately, this bit is not for the best, but would be a whole other question and not for me to ask). I grew to like Adam a lot, though I can see why he is no longer a good match for my sister.

My mother has emailed me asking what to get him for christmas this year. Aside from the fact that it’s still only October (argh, why) – is this a lovely-gesture-go-ahead situation or very-kind-but-not-appropriate one?

In her email my mother said ‘after all he is still my son-in-law and I’d like to get him something’ along with neutral suggestions for gift cards in places I doubt he shops. Mentioned that she knows Kate is who she ‘should’ ask but also not, because it would obviously be a sore point.

Kate and Adam are not yet divorced, I am unsure about timeline here – surely isn’t the issue though – the fact that they are ending their relationship is. Technically he may be her son-in-law…but? I don’t know. I’m not sure what my ‘but’ actually is.

Possible scripts?
‘I’m sorry I don’t know what the best thing to do it – up to you’ – this feels like a cop-out – and he might end up with unwanted gift.

‘Yes that sounds kind and lovely – but get him a voucher for (shop I know he likes) instead’

Something else?

Because myself and partner had a good relationship with them (hung out as a 4 a few times), we sent them both a graphic novel each and a short note saying we love/care for you etc.

Sister loved hers, but no reply from Adam. I realise that he has many other things on his mind and no acknowledgement is absolutely fine – just made me think even more about the etiquette and if perhaps sending a gift (meant as kindness/distraction) was in fact not appropriate for the situation?

Also – they have no kids. Presumably if they did he would be much more likely to be involved with our family still post-divorce. As that is not the case – what is the etiquette here?

Any help so much appreciated!

Thank you
Etiquette is hard!

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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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Hurricane Joaquin…everybody ok so far? Be okay.


My wife (Carole) and I (Clark) have four children and share our home with a childless couple (John & Priscilla) who I met in college. We’ve done so for roughly two years now with surprisingly little friction.

Recently John talked to me about how he’s come to the realization over the past year that he is polyamorous. The rest of us are not.

John also confessed that he’s had a crush on someone outside the house for a few years and that there are other infidelities over the course of his marriage.

I am having a difficult time discerning if this is actual polyamory (which I am not terribly familiar with) or just rationalization of bad behavior and a desire to have shackles taken off so he can date other women without guilt.

John discussed the possibility of romances (plural his) going forward and not liking the idea of primary/secondary relationship – so in theory these other women would have the same status in his life as Priscilla.

Putting myself in Priscilla’s shoes – this would be hard to swallow. I fear that our happy home is about to be torn and I am hoping for some help with resources / tools I can use to help them both while maintaining healthy boundaries.

(I am not concerned about having random lady friends over with children about – before moving in we all signed a contract that included the right of any one of us to veto someone coming over if for any reason it made us uncomfortable. John will have to get any lady friends approved by his house-mates before they can come over or will have to leave.)

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