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Captain Awkward’s Dating Guide for Geeks

Ghostbusters shooting their plasma guns

“Isn’t it about time we crossed the streams?”

Dear Captain!

My awkward problem is this: I’ve been dating this guy for about two and a half months. He’s nice! I like him! He seems to like me! I’ve stayed over at his place a few times and he’s been to my apartment. But he won’t introduce me to anyone in his life (and isn’t that keen on meeting anyone from mine) and it’s starting to weird me out. Am I overreacting?

We see each other a couple of times a week, usually. He won’t hang on weekends, because he goes to visit his family in another city. Though sometimes, he has said he is going to visit his family and then tells me he changed his mind and stayed home in this town and hung out with his brother all weekend, but he never suggested I meet his brother. It’s like he is Mr. Secret Squirrel about his life. This week he is hosting a friend/ colleague from his company’s office abroad so he told me we can’t see each other as much because he has to work/hang out with this guy until fairly late every day.

At no point did he suggest that I come meet this person and say hi and we have coffee or something low key, though he did discuss with me tourist places he should take this guy. I felt too awkward to ask directly, “hey, your colleague buddy sounds cool, I’d like to meet him”, because he was so cagey (he has not even told me the guy’s name). They are spending the weekend on day trips and I understand why he might not want to invite me to those — he wants to spend time with his buddy & colleague, that’s all cool. But not to introduce me at all seems odd?

I have wanted to introduce him to my friends (I am an ex-pat in this country and my friend pool is fairly small because a lot of people have left (we live in a war zone) but he is a bit dismissive of the things we do – boardgames, Cards Against Humanity etc. Not openly hostile, just “oh that seems weird”.

I have no clue why he doesn’t seem to want me to meet people from his life, and I know it’s pointless to speculate. He is very introverted and maybe it doesn’t occur to him that people can socialize? Is that making excuses for him? Or am I overreacting?

How can I raise this with him without sounding weird or pushy or something? I’m getting really tired of it!

Thanks for any wisdom and insight,
C.

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Let’s play the game where we answer the questions people typed into search engines to find this place. Punctuation added. Wording unchanged. 

1. “My bf won’t choose me over his brothers that are rude to me.

I don’t know what the nature of this choice is, like, probably your boyfriend won’t ever cut off or stop talking to his brothers on your behalf, but your boyfriend should definitely stick up for you when and if people in his family are rude to you. 

2. “When he says he doesn’t have time or focus for a relationship.”

Time and focus may in fact be factors, but also, “he” doesn’t want to be in a relationship with you. I’m sorry, that sucks to hear. Move on from this prospect, is my advice. 

3. “How to turn down a friend down politely convincing her you love but can’t engage in a relationship right now.”

This is the wrong way to go about it. If you don’t want to be in a relationship, just tell her “I don’t want to be in a romantic relationship with you, I’m so sorry, but I value you very much as a friend.” Let her heal for a bit and then you can most likely be friends again. If you use the “not right now” excuse you leave her hanging and hoping, and it’s going to be so much worse.

4. “What it means when a girl say she does not think it will work out.” /”What did she mean by saying we can’t cope with each other?”

Most likely translations: “I don’t want to be in a romantic relationship with you, but I’m using neutral language like ‘it won’t’ work’ to try to spare your feelings.”

5. “How to respond to a compliment on your looks.”

From an acquaintance, not delivered with a leer, like, “You look really nice today?” a good answer is “Thank you.” It’s what people expect to hear and will complete the conversational circuit with maximum efficiency. 

Yelled at you from a moving car? It’s not a compliment at that point. 

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As of August 28, comments are closed. Letter Writer: Go read some books by women, try out some new social activities, GO TO A REAL THERAPIST, and be well.

Dear Captain Awkward,

So I’m a guy, 20 years old and totally devoid of any form of romantic relationship. Ever. I’ve never so much as held hands with a member of the opposite sex, never mind anything else. I’m getting incredibly lonely and yes before you say it, I did behave like a nice guy tm once and just once. I was an ass, I made an incredible fool of myself, I traumatized my friends and worst of all, I hurt that poor girls feelings. She wasn’t the nicest person and took advantage of me, but I hurt her feelings and I made sure when I came to my senses that I apologized, regardless of what she’d done, I messed up. Before all that happened, I was an incredible jerk, an arrogant piece of shit with an intellect to match and zero attachments to anyone. I hated the idea of feelings and I shut them out and didn’t do friends (ironically this is when I received most attention from the females). For most of my teenage years, I didn’t need people and I didn’t need love.

I’m literally petrified of making the same mistake again and of ever hurting another living soul again, I’ve been bad, I’ve made mistakes and I’ve taken advantage of people, now I’m trying, very hard not to be that person again and that includes treating women as people, with thoughts and feelings, hopes and fears and dreams. It’s difficult in the uni dorm I’m in, considering most people I meet socially are either drunk (I’m stone cold sober) or do the whole ‘one night stand’ routine which to me is appalling. The few people I’ve really sparked with are all in relationships.

I’m lonely and very different, I’m eccentric, have eccentric tastes and I’m a lot more mature then most people I meet in most social settings (I’ve been regularly mistaken for 40+ when I was 18) I’m also a romantic whose entire cultural upbringing utterly rejects the idea of genders freely mixing and all that cabal. Pretty much means my social skills are shit. I can out-argue almost anyone and I can debate exceptionally well but I’ve zero social skills that aren’t an argument, sports or one of my passions (which many people do not like) I’m regularly putting my foot in it in casual conversations and I have been told in the past that I am far far too intense. 

On the plus side, most of my closest friends are all female (I do not and have not had romantic feelings for any of them) and they’re great people but they all offer conflicting advice on what my problem is. I’m fast becoming isolated, I’ve zero self confidence and my self esteem has taken a nose dive, a combination of truly looking into the mirror for once and a mystery illness. I don’t think I look handsome, but a lot of people have said that I do. I get really confused and I pick up a lot of body language, but I have no understanding of social cues. It’s like I’m trying to read Swahili.

What on earth is wrong with me? Am I incapable of being loved?

Awkward & Lonely

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Dear Captain Awkward and the Awkward Army,

Long story short: my kind, hilarious, handsome (ex) boyfriend and I just broke up because after two years of things being “great!” we realized that nagging “…but maybe not the ‘forever’ kind of great?” wasn’t ever going to go away. It is very, very sad and very, very hard and everyone is crying a lot and gazing listlessly out windows listening to Bon Iver and wishing this wasn’t our lives.

That being said – we would like to still be friends in a real and meaningful way, and I’m not sure how to navigate this for a few reasons:
- I have some exes who I’m friendly with, but they were all “we dated for 6 months” or less exes, and the kind of “friends” we are is, “we can be in gatherings together and it’s mostly fine and not awkward!” and, “we comment on each other’s funny facebook statuses!” not, “you are the thing that makes me laugh when my day is terrible” or, “you are my partner in crime and adventures” or, “I call you when I just want to talk” friends.

- He has no exes who are his friends, and only one with whom he is on still-in-contact friendly terms.

- We are VERY NEWLY broken up, and I don’t want to mess this up by rushing to friendship before every time I see him and then remember we’re not together it feels like a sharp tug on my Golden Retriever of Love’s leash (you know – that feeling of stabbing knives and despair). But also don’t want to “give it space” until seeing each other turns into this unnatural production.

- I suspect that, in my heart of hearts, I will be unbelievably ungracious about his new girlfriend(s), when their time comes. He is, truly, the Perfect Guy (Funny! Kind! Unbelievably hot! In possession of the world’s best beard! Not into the DC-style of one-upmanship that is the worst!) – and I KNOW that he is going to be snatched up by some really perfect waif-y-type-woman in basically seconds. I “KNOW” this in part because he is amazing and in part because This Is My Greatest Insecurity (jerkbrain says: “What if he dates some blond, no-makeup-wearing, athletic woman next? Will that ‘prove’ that our relationship wasn’t meant to be because I WAS UNWORTHY?’“) and I react to it by having a lot of possessive crazyperson thoughts that I keep mostly to myself, but that eat me up inside.

Can you help me figure out how to navigate, “I love you, but need to be falling out of love with you” and “I want you to be important in my life – but also need to let go of feeling possessive of you?” We’re both going to make an effort to communicate a lot about making sure we’re respecting one another’s boundaries but this re-definition is hard and unfamiliar to me and I just want to cut right to the part where seeing him doesn’t feel like stabbing and I don’t want to push his new girlfriends into volcanoes.

Thanks,
Let’s Be Friends

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Hello Awkwardeers,

I was recently on a double date with a family member, their spouse, and an acquaintance of said spouse. The family member sold it to me as a “try it out and see what happens sort of thing” but I’m not sure if that’s how it came across to the Acquaintance. Acquaintance really seemed to think it was a Real First Date(tm) and now I have no idea how to manage this.

Basically, I’m a single female and I’ve only been completely on my own for a half a year, and I’m only just being able to define who I am and what I want. I’m really not interesting in any romantic relationships, unless the guy is a Super Amazing Fantastic Wonderful and All Around Good Guy. And Acquaintance was perfectly nice, but not enough of a Super Amazing Fantastic Wonderful and All Around Good Guy to get me out of my aggressively chosen singledom. Which is not his fault, I’m just not interested. In addition, I basically had a mini panic attack when he added me on social media after our date/not date. So where do I go from here? How do I let Acquaintance know that I’m not ready for a relationship and probably won’t be for a very long time, and it’s got nothing to do with him?

Thanks,
Awkward Single Lady

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Dear Captain,

In essence, I absolutely adore this girl, but there’s someone else, and she has problems being away from home. As a disclaimer: this isn’t some crush, or the case of a naïve adolescent. This is my fifth relationship (though I wouldn’t call myself experienced in relationships). I’ve dated this girl, and known her for over a year, during which we’ve been comfortable friends for long stretches of time. I want her in my life, at least as a very close friend.

Lets call her Emma. We met last August in college, and very quickly, naturally, spilled all our feelings and pasts to each other. Emma was emotional and had a troubled history of depression. I’m an open and helpful person, so I was more than happy to be there for her. She didn’t need me, but felt much happier with me around. She was single, but had lingering feelings for her ex, who she’d gone out with for two years, but had broken up with because she didn’t want to do long distance in college. His presence was visibly ruining her emotionally. At this point I had no intention of going out with her – I was more than happy to have her as a close friend. Eventually, I had a sit-down with Emma, explaining to her she wouldn’t truly be happy if she didn’t let him go.

About a week later, Emma stopped contact with him. She was noticeably happier, and I was proud to have helped her. I started to develop feelings. She had had feelings for a while, before she broke things off with her ex. The natural progression of our friendship led to us going out. This lasted over 3 months, until break. She went home to her closely knit friend group, which included her ex. My family had just moved to a remote location with a harsh winter, and was alone for break. It was hell.

This took an emotional toll on me. When we returned to campus, things weren’t the same. She broke up with me after a week with no clear reason. Emma got back with her ex shortly thereafter. It was because her ex was more accessible over break than I was, by default. It wasn’t my fault.

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Dear Captain,

I couldn’t find a similar story, and I don’t know how strong a bro-relation is, so I’ve been quite confused for a while. The history about this story is bigger, but I only want to point out the main things. This is my story:

It all started a year ago, I met this guy Jimmy, which I fell in love with. We became friends. I gathered my courage and confessed to him. The response I got was not what I expected… His reply was just we’ll see what happens. After a month he didn’t took the effort to make it work. We didn’t saw each other at all. For me it was pretty clear that he didn’t wanted to start something with me.

A month later I went to a party at his house. For me this party was the opportunity to find out whether I still had feelings for him. At this party we all drank a little too much and a friend of him, Jason brought me home. I think you can already predict what happened. We kissed, nothing bad yet, except for the fact that this guy has a girlfriend…The next day, when we got sober I talked with Jason, and we decided it was a mistake and never mention it again. I felt horrible for making him cheat, and was so confused about my feelings. So it was easier for me to not seeing them both for a while.

A few weeks later, Jason contacted me. He wanted to see me and I agreed to it. I think I was being naïve, for not seeing what he wanted and we went a step further. His girlfriend still didn’t know anything about it.

A week later I met up with Jimmy at his house. Jason was there too. We talked about cheating and Jimmy hated people who were cheating, he couldn’t understand why someone would do that. At the end of the night he brought me home. We talked and I wanted to know what I meant to him. He confessed that he didn’t want a relationship right now. His ambitions are too big to settle down at this moment, but his feelings towards me can still go any direction. So my secret affair with Jason continued. After a month he ended it all. He confessed our affair to his girlfriend, and he wants to stay with her.

Months passed by without seeing them both, until yesterday. I went to Jimmy’s house, where they both were. The weird thing is that it didn’t felt awkward at all, sitting between them. For all I could say, I got the feeling that Jimmy was hitting on me. For what reason I don’t know, did Jason told him anything? Or is he finally ready to settle down? Just all those assumptions, makes me insecure.

Also I just don’t know what to do if I ever get serious with Jimmy. Am I obligated to tell him about Jason? I still have a weakness for Jimmy, but I don’t know if he can ever accept me for sleeping with Jason and if I would damage his friendship with him.

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