Tag Archives: Dating

Happy 2013, everybody!

Dear Captain Awkward:

Here’s the deal. About 4 months ago I moved with Boyfriend about a thousand miles away from my family and friends for a job offer he received. The city we moved to is big and we figured that it would be easy for me to find a job there. That has not been the case, and I am still unemployed. That’s not the problem. 

I have decided to end the relationship with him. It has been waning and I am no longer happy in it, so it is time to go. I have the breakup planned and I will be moving back with my parents while I wait on some jobs that I have applied to in other places. 

My question is this. How do I let the friends I’ve made know? Boyfriend and I live together, so as soon as we break up I will be leaving and I likely won’t get a chance to see them again. I want to have a chance to say goodbye, but it doesn’t seem right to tell them I’ll be leaving before the breakup happens. I really like a lot of them and I was enjoying getting to know them, so I will miss them and don’t want to just leave without even a word. 

Any advice would be appreciated! Thanks!

Moving Friend

Dear Moving Friend,

I started to answer this in a quick email, and then I realized that a lot of people could probably relate to the awkwardness of letting people know about a breakup.

I suggest that you set up a casual farewell event before you leave town. Something where you will hold court for a few hours at a local bar or coffee shop and whoever wants to stop by can stop by (and you can sit there with a book if you like). Don’t invite people  yet – you are correct, it is pretty horrible to inform the friend group of a breakup before you do the actual breaking up –  but pick a venue and block out the time.

Then break up.

Then, I suggest an email, which you can tailor to each person as necessary.

Dear friend, I wanted to let you know some sad news. Sadly, (partner) and I have split up, and I’ll be heading back home where my family lives as of (date).

Your friendship has been really important to me since moving to (city), and I definitely didn’t want to leave without saying goodbye. I realize it’s last minute, but if you have a bit of time on (day), please stop by (place) between (time and time) and have a drink with me if you can. If not, I completely understand and hope we can stay connected with Facebook, Twitter, etc. and that you’ll look me up if you are ever in (city).

Thanks so much for your kindness and company these past few months, it’s meant the world to me.

Best wishes,


Does that work? It lets people know the facts & conveys your affection, and as a bonus, it saves your boyfriend from having to do potentially humiliating work of notifying mutual friends about what’s up. Hopefully they can reach out and buy him a beer once you’re gone.

Good luck getting through a really sucky time with grace and a minimum of emotional and logistical carnage, and good luck finding work that you like. Breaking up sucks even when it’s the right decision. I’m impressed with your clear head and your desire to be kind & mannerly while also taking care of your own needs on your way out the door.



Hey Captain!

My question is on the ‘he’s not that into you’ theme, and in particular about how to respond appropriately.

I recently decided to try to reconnect with an old friend. We used to be flirty and have some pants and head feelings for each other, but I wasn’t ready for a relationship so nothing ever happened. As far as I know there was no animosity, but inevitably we lost touch, saw other people, blah, blah, blah. Several years on I thought it would be nice to see how he was doing and dropped him an email. Our few brief initial exchanges were very light-hearted and friendly – smileys and everything – and he suggested meeting to catch up. However, his emails about arranging a date suddenly became very abrupt and infrequent and lost any markers of enthusiasm. Going by your awesome maxim that people that are into you (both friends and dates) are easy to arrange things with, I figure he’s changed his mind and doesn’t want to meet up after all. No biggie – I’m happy to leave him be! And yet he’s still going through the motions of trying to arrange it, thus leaving an y actual decisions and responsibility about whether or not we do meet up firmly in my court.

Now if he does want to meet then I think it would be nice to catch up, but I certainly don’t want to sit through an awkward evening of small talk with someone who doesn’t want to be there but can’t admit it. 

Is there a script I can use to ask him to use his words? Or even to bow out gracefully without looking like a trifler? Is ‘Actually, you don’t sound like you want to meet up’ too weird or pressurizing of an email to receive from someone you barely know any more?

Thank you!

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Hello Captain and Co.!

Here’s my super sad background: I am a fat (stats redacted), black, straight, able-bodied, 33 year-old woman. I haven’t had sex in 13 years. I’ve come to realize that my one sex partner kinda raped away my virginity. I basically kept dating and sleeping with my abusive date rapist. Yes, I’m in therapy.

Despite my unfortunate past, I’d like to date but have been extremely unsuccessful. I try very hard not to think that it’s because I am fat and black and over 30 and both inexperienced AND damaged goods, but it’s hard to stay positive. Online dating hasn’t worked. I’ve been on exactly one date and I’ve tried online dating on and off since 2006. Set-ups are rare and typically don’t pan out, though one did result in 6 dates with a man who was WRONG for me, but it was still something!

I have, probably ridiculously, got my eye on this beautiful specimen of a man. He’s like a kind, friendly, sorta urban Lex Luthor. I may not have a chance; I think I have a lovely face and I do my best to look pretty, but men don’t seem to look beyond my size or blackness or horrible personality? I end that as a question because I don’t know what my problem is.

I try my best to smile and make pleasant conversation with Mr. Luthor. I even emailed him once as a follow up to one of our talks. (He wrote back!) I don’t know if he’s single, but I don’t think he’s married. If he isn’t single, I’d like to be his friend because someone that beautiful and kind must hang around other beautiful and kind people, right? Maybe my new friend could introduce me to someone great! And he seems pretty great. Win-win!

I think he has gazed at me more than once during our weekly chats, but I’ve been talking myself out of those thoughts because really? I’m so out of practice would I even know if he was? However, when he talks to me, I sometimes get the feeling that that’s how he’d talk to a friendly puppy, like even with all the possible gazing, he may not see me as a woman to maybe do pants things with.

Can you teach me how to excuse his beauty and not get so flustered when he’s around? Can you teach me how to show him that I am a woman, dammit, but in a way that won’t get me fired because our interactions happen when he visits my workplace a few times a week?

Thank you for reading and helping!


Please go read the entire Shapely Prose archive. Read this post twice, and then bookmark it. You’ll want it later.

Then read this.

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Count Rugen from The Princess Bride looking saturnine.

We are men of action, and lies like “It just happened!” do not become us.

Dear Team Awwkard,

Ok so here it is: I’m back at university after having to take time out due to depression and a very bad reaction to meds last year. I have a feeling that the depression was in a large part due to the relationship I was in at the time where my partner had Major Depression and Other Issues which meant I spent a lot of time trying to manage his crises, get him to seek help etc and deal with the emotional abuse that he threw at me when he had an ‘episode’. That relationship ended in February and I am much happier now, breaking up with him was a bit like stopping banging my head against a wall. I made the decision that since this is my last year of university and I am going to be thinking about jobs/a career/relocating that a serious relationship isn’t something I am looking for, because I want my decisions to be focused on what I want.  My family have been wonderful and supportive throughout everything and I am happy to be back at university although I still worry about things like work habits and slipping back into how I was behaving this time last year.

Over the summer I got a job at a pub to try to pay off my overdraft and met J. J, who has a girlfriend, worked in the kitchen and as most of the staff who worked at the pub tended to socialise after work together, we became friends, then good friends. He has just started university and I went to visit him during his freshers week because we enjoy going out together and he is fun to hang out with. Well the first night he explained that him and his girlfriend had decided that they were allowed to sleep with other people that they thought might be good relationship material. Their relationship is iffy, something I see as a combination of going off to university, the two year itch and probably other factors as well although we don’t tend to discuss it very often. Long story short, we wound up getting drunk that night and having sex. Very good sex. That happened again the next night and the morning after too.

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Dear Captain Awkward,

I feel this is essentially a non-question, and you will just tell me to “use my words”. But I think I need to hear it, so bear with me please.

I am 19 years old, and attending university. All my life I have been a nerd of the science/tech variety, but I never had any problems navigating social events. I am rather outgoing, and generally not awkward, but rather perceived as witty (if a bit snarky), knowledgeable and fun to be around. Yet up until now never did I draw a girl’s attention towards me (except for being interested in friendship, which is not a bad thing in itself) – and I did not really try to because those I were into were in relationships already. But lately there is this girl in my social circle I keep running into at parties. She is beautiful, with a sense of humor I can connect with and a relaxed attitude to life that mirrors my own. In short, I like her very much. After we met a few times, and had quite a great time talking and drinking and just being there with the others, at one occasion she kissed me. We made out a bit further on that evening, but a mutual aquaintance began drunkenly insulting her (erm…don’t ask, he is another story) whenever no one else was listening, so she left. And this is where the awkwardness begins: We couldn’t see each other for over a month, for reasons none of us could influence, and when we met again, both of us behaved as if nothing happened (I had convinced myself she wasn’t really into me for whatever reason, and whatever she thought, I don’t know) This continued until recently, where we walked along a street at night and she just turned to me and kissed me again. And again. And for the rest of the night (which continued through several bars) we made out and talked and just seemed to everyone watching like a newly formed couple (according to my friends observations, at least). I still didn’t know what to think of this, and when we met again at a party a few days later, the same thing happened. I sat beside her, she leaned against me, and we kissed.

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Dear Captain Awkward,

Three years ago, I skipped 8th grade and started high school.  Most people were awful about it, but several girls and one guy (ONE! In my WHOLE GRADE!) who actually spoke to me treated me like a was a human being with thoughts and feelings, because I AM.  Being sad, lonely, and scared, I became close to these people, and quickly developed a crush on That One Guy.

Everyone has a That One Guy (or Girl), who makes them feel happy and giddy and better on a crappy day, at some (or many) point(s) in their life.  Unfortunately, my current That One Guy has solidly Friend-zoned me.  He is kind and smart and athletic and funny and, while he’s not gorgeous, his personality makes him seem to me much more attractive than average, which is likely how a stranger would see him.  Yet he is COMPLETELY oblivious to my feelings.  Once, he asked a friend of mine (who didn’t know about my feelings for him) to Junior Prom IN FRONT OF ME, then got confused when the next day I said I probably wasn’t going.  That’s how oblivious he is.

Anyway, I have recently decided I need to get over Mr. Oblivious, because he is now dating someone. (Another sort-of friend with no idea about my feelings. YAY!)  I was literally attacked by the thing sitting on top of my Facebook Newsfeed telling me that they are now in a relationship.  I need to get over him.  It is not healthy to have feelings for this guy anymore, because at this point if he ever did ask me out, we’d be starting at such unequal levels of FEELINGS that it would have disastrous results and, more to the point, he is Not Interested, which makes him Not Worth It.

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African Violet, photo by on Flickr, shared under a Creative Commons attribution-noncommercial license.

Photo by on Flickr, shared under a Creative Commons license.

Dear Captain Awkward:

A year ago I broke up with a girlfriend of three years. Before she was my girlfriend she had been my best friend for over 10 years, and was someone whom I deeply trusted with pretty much everything. When we broke up it was very messy and she said some very hurtful things to me, things that, due to all those years of knowing each other, she knew would hurt me pretty deeply. And it did. But that really is not my core issue.

I’ve been suffering from depression for a couple of years (approximately 2 years), and only recently have I started seeing a therapist and taking meds to help me with my issues. And it has worked wonderfully. But those sessions have made me realize a lot of really troubling things about my past relationship. 

The doctor brought to my attention that her behavior had been pretty controlling and abusive towards me, even before we started going out. A small list of her behavior: she would get upset when I went out to hang out with other friends that were not her; also, if I had planned an outing with her and a few others, she would get upset that there were other friends there appart from her. If I liked things that she didn’t like, she got upset, same if I didn’t like things that she did. It got to the point that I would just agree with her so she would’t get passive-agressive with me. She also would get angry with me for the strangest things, like, messing up the structure of a sentence or misremembering the name of her college. She would start berating me for forgetting something so easy and so on. And on one occassion, when one of my friends was staying over at my room (I currently live in a college residence) because she was sick and her roomate wasn’t there, while i was skypeing with her, she got very upset and demanded that I tell her to leave, when I didn’t she got angry and hung up. I got so distressed over that that my friend took to leaving to her room whenever she called me via skype. And whenever I called her out on her behavior, for some reason, I would always end up apologizing to her for saying anything. And she could be so condessending towards me that she made me feel bad for things I didn’t feel bad for before (I’m really short, I don’t have a complex about it. But she once told me that she avoided heels when going with me so I would’t feel bad. I was hurt and for years I didn’t know why).

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