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Tag Archives: breaking up

Four letters about The Guy Who Would Be Perfect If Not For That One Dealbreaker Thing. I didn’t publish the 5th of this ilk that came in this week, which was about a perpetually-unemployed-and-not-trying, bad-in-bed man who was also mean. That one was too easy (Bees! Run!). These are harder because people don’t have to be evil to be not quite right for you.

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The monthly(ish) roundup of the questions people type into search engines to find this blog.

1. “My partner thinks I have genital warts but I have herpes what do I do?”

Both of you should get a full STI screen, if you haven’t already, and talk about whatever you find there. (‘Cause maybe it’s both). Or, if you’ve just done this, say “We thought I had HPV, but the screen showed that actually it’s herpes. You should get screened, too.

2. “My girlfriend is rude to my parents.” 

“Hey, you were pretty rude to my parents tonight. I don’t appreciate you (specific rude thing she did). I think they deserve an apology, and I need you to calm that whole thing down.”

If you bring it up, does she acknowledge the behavior? Is she rude to other people who aren’t you? Is she rude to your folks even after you talk to her about it?

3. “I joined a dating website to hurt him.”

Spite Dating: seems totally reasonable and like it will bring you and your Spite Dates nothing but happiness!

Or, ahem, maybe this is a good sign that whatever relationship you’re in has run its course and it’s time for you to find the exit, take some good care of yourself, give yourself some room to mourn and heal. Join a dating site to remind yourself that you have options. And then, when you’re ready, use that dating site and find new people who will be into you the way you want them to be. But do it for yourself, not at your (soon to be) ex.

4.” ‘I love you as certain dark things are to be loved in secret, between the shadow and the soul’ what does the line means?”

Reading the whole poem, it seems to me the poet is describing a love for someone for reasons that would not be obvious to everyone, in a way that isn’t necessarily healthy or a good idea, but is true nonetheless. It reminds me a little of the song My Funny Valentine. Lit Majors of Captain Awkward, what say you?

5. “I just don’t feel ready enough yet to be in a new relationship because I’m tired and now I want to be alone.” 

Embrace the alone.

Make your living space exactly what YOU want it to be. Eat foods YOU like, watch movies YOU want, listen to YOUR favorite music. Throw yourself into work, into school, into creative endeavors, into meeting new people or trying new things for their own sake. Or curl up under a blanket and wait out this eternal February with a good book. Spend time with your friends and family and people who love you. Be really nice to yourself. Heal. Get some rest. Feast on your life.

And when people ask, in a well-meaning fashion, if you’re dating anyone new or if you plan to, smile and say “I’m sure I will someday, but I’m really enjoying being alone right now.

There’s this picture of Katie Holmes from a while back that people were criticizing for being “frumpy” or whatever. I kind of love her outfit and would wear it in a heartbeat, but mostly what I want to say is “LOOK AT HER SMILE. THAT IS A PERSON WHO IS FEELING LIKE HERSELF RIGHT NOW.”

That’s you. Alone. Walking through the world like you know a secret no one else does, and the secret is that life is huge and amazing and you are strong and wonderful and there are all kinds of love in this world and relationship-type love is only one of them.

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Dear Captain Awkward,

I married my college boyfriend T three years ago, but our marriage became pretty awful. This past summer I went to a month-long program for my job and met M, who is honestly the most amazing person I’ve ever known. He gets me in a way no guy ever has. When we said goodbye he kissed me and it was like fireworks going off. We stayed in touch every day and realized we were in love. I knew I wanted to be with him, so I was upfront and honest with T about everything. T asked me if I would cut off all contact with M and go into counseling with him, but it was too late for that.

I flew to where M lives a few times and everything went to another level. He’s married too and has been unhappy for a long time but it’s more complicated because they have two kids. I moved out from the house T lives in (it’s owned by his company so I was the one who had to leave) and that was really hard. At first T was letting me stay a couple of months, then changed his mind and I had to leave in 2 weeks. Then he refused to keep our cat even though the apartment I found doesn’t allow pets, and gave it away to someone else. M is allergic but said he’ll live with them because that’s how much he loves me.

This summer M and I are moving in together. We’re keeping our current jobs until then for finances, and it gives him time to figure out how to tell his wife and kids. T and I are getting divorced, and I’m starting to feel happy again except T is telling everything to our mutual friends from college, including the girls I lived with, who are more my friends than his. He insists on telling all the details and blames me for breaking up our marriage. He’s prejudicing my own friends against me and against M, who he’s never even met. I’ve asked him to just say that we had irreconcilable differences and we’re moving on with our lives, but he refuses and says it’s his story too and he can tell it however he wants.

How do I talk to my friends without having to defend myself against everything? How do I show them how happy I am? I want them to meet M so they can see how good we are together, but feel like T has poisoned the well. I’m following my heart and it’s been really hard and I need their support, but I feel like T is actively trying to destroy that. I’m scared to lose them. What can I do?

Following My Heart

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Dear Captain and Co,

Almost 3 years ago I broke up with my then-boyfriend of 6 months.  We’d been friends before, and due to being in the same friends group, stayed friendly afterward.  I thought we would be able to make better friends than a couple, but I didn’t push the issue, as it was obviously awkward.  Then we both graduated college, moved to different places, and lost touch.  About a year, maybe year and a half later, he defriended me on Facebook, so we’ve been completely out of touch for a year and a half now.

My problem is that I owe him an original short story due to a lost bet.  The bet happened at the start of our relationship, and while I made notes about the story I intended to write, due to school and stuff, I never actually got it written.  I’ve had the time to write the story for at least a year now, but haven’t because I’m not sure that it’s still appropriate for me to contact him.  This keeps bothering me because it feels like a broken promise.  I promised a story and I didn’t deliver, and there was no time limit on the delivery so I could still keep the promise.  But he chose to defriend me and I want to respect that too.

Whenever I think of sending him the story, I think of saying in the email something like “I still owed you a story, you don’t have to get in contact if you don’t want.”  But that feels awkward enough that I haven’t done it.

Should I just write this off as something I won’t be able to complete?

~ Open to Being Friends

Dear Open:

Of course you should write the story, if only to get it out of your system and check “wrote story” off your mental to-do list.

But you shouldn’t send it to him, not only because he closed off contact with you, but because it’s your story now.

This dude passed through your life for good or for ill, and you have memories and feelings and lessons that you’ve earned from that that are part of your story. That story is yours to write, to submit, maybe to publish, to share, to develop. Don’t offer it up to some dude you broke up with to pay off a bet he’s probably forgotten about. Your muse doesn’t necessarily need to be your audience.

When you break up with someone, here’s what you owe them:

  • Communicating your decision in a clear way and not making them guess or find out about it on Facebook when you change your status to “Single” or “It’s complicated“, i.e. “Not quite single yet but definitely open to fucking new people!
  • Paying back money and giving back their stuff in a timely fashion and sorting out legal issues like leases, rent, custody of pets/offspring as fairly as possible.
  • Respecting their wishes about (lack of) communication and making your own boundaries and expectations clear.
  • Doing what you can to be kind and fair, but not at the expense of your own well-being.

You don’t owe them further communication. You don’t have to be friends.

You don’t owe them telling your story in a way that makes them look like the good guy.

You don’t owe them fulfilling old promises. Ever heard the phrase “All bets are off”? It definitely applies after a breakup. That’s your story prompt:

“‘All bets are off,’ she said…”

One way you can find closure after the end of the relationship is to reclaim all the stuff that is yours as YOURS.

If you are having trouble letting go and need to avoid all things that remind you of your ex (family, ex-friend, etc.), so be it. I hear you, and you should do what works for you. But if you’ve let the person go just fine, you shouldn’t have to give up your love of things you love just because they are associated with a past love affair. So what if your ex recommended that great novel or movie to you. You loved it? Cool, it’s yours now, part of your canon. Your favorite restaurants and bars and coffee shops and bookstores? Yours. Go there, head held high, and eat the delicious food and drink the delicious drinks. Friends you made during the relationship, who you would still like to hang with? Call them up. If you genuinely care for each other and have things in common besides common knowledge of some dude or lady, the friendship will work just fine. If it doesn’t? It wasn’t meant to be and you can let it go. Loving someone means letting a whole bunch of new experiences, associations, and inspirations into your life, and you’re not obligated to let go of stuff that you love (or worse, creative work you made) just because the person didn’t stick around in your life forever.

Letter writer, I pronounce you sole proprietor of any stories you write as a result of your relationship with one former datepartner. I also absolve you of the obligation to write any story whatsoever unless you want to for your own reasons.

Twice a year, I hold out the tip jar and invite readers who are able to kick in a few $ to support the site.

If you like what you read here and find it helpful, please consider making a (non-tax deductible) gift  through PayPal or  via Dwolla (for which you must be in the USA with a bank account).

In the past I have sent a short story, The Best Dog In The World, or a link to my short film (now publicly available on Vimeo) as a reward.  I don’t have anything specific to send out this year, but anyone can watch or download those, no donation required.

We now return to our regularly-scheduled programming.

Dear Captain Awkard:

So I’ve been dating this Sagittarian for 8 months. It was going swimmingly and due to his couple of months free waiting to get exam results and find a new job, along with me working for myself and being able to take loads of time off, we were intenso – inseparable for 3 months. Mix up his exotic hotness, ambition, brains, resounding (seeming) lack of baggage, patience, easygoing nature and ability to deal with me. Slather on some pretty great sex, a holiday in Rome, my friends loving him, lots of late night spiritual and philosophical convos and I was fully baked. He’s only 26 and I’m 28 but sure cool.

Then he gets the job he wanted. Head and neck surgeon and pretty full on, but only 8-5 and no weekends. I would have been fine only for 2 things: sex took a massive nose dive and he’s absolutely exhausted all the time.

I’m a Gemini. Fairly well-adjusted but I get bored of the trivialities of 9-5 life, that’s why I’m an entrepreneur. I also adore traveling and love my work, I see life as being about relationships and experiences. I feel as though he’s choosing his career over the rest of his life, including ME.

Now I’m a bitter hag about the sex, having asked if it’s because he’s gay (both honestly and nastily), or just doesn’t fancy me (ditto) or if he has issues about sex (not much experience/possible mother issues or whatever) and he swears it’s none of these things, he’s just tired. He also now thinks I’m a nympho, which is ridiculous.

He can’t seem to sleep earlier than 12 and gets up at 6 so I KNOW he’s tired but he has to take responsibility for that himself, I don’t force him to stay up or eat late! He’s trying different diets, gave up smoking 2 months ago for the first time in 14 years, getting exercise, is going to try yoga, but it’s not working so far.

I feel neglected, betrayed, disappointed. On top of that he’s not very romantic or good at expressing his feelings verbally. Not terrible but not great. We’ve entered a massive power struggle and are constantly bickering, mostly started by me. Throw in the fact that his 6 month contract ends soon and he may have to spend much of his career moving around the country. I am fairly free to go with him but my LIFE is here in London and I’m not the type of person who wants to be traipsing around after a man. I feel really badly towards him and I know that I’m pulling away because I don’t want to compromise myself and/or get hurt. Oh and I don’t like his mother.


Dear Star-Crossed Gemini:

I consulted the stars, and they said that when a person starts an intense new job and makes a bunch of lifestyle changes all at once, it might take a few months to get into a new routine that works. Even with a relatively predictable schedule, working as a surgeon full time is no joke and it is not surprising that he would be physically and mentally exhausted as he tries to climb the learning curve. He’s spent most of the last decade training for this moment. It’s possible that you guys just have mismatched sex drives and would have found that out over the long-term anyway, but even people with very high sex drives are affected by stress and major changes. Whatever is going on, bickering and other “massive” “It’s your career vs. ME” power struggles are not going to make it better. I mean, what is the most sexy sex of all? Making a wild guess, it’s not the “I’m doing this to prove I’m not gay!” sex that you’re browbeaten into by a resentful partner.

Then the sun chimed in that you should stop describing anything as “exotic,” most especially a romantic partner.  One by one the planets nodded their assent.

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We got the following request yesterday:

Hello Awkward Helpers! I am thinking that I (and maybe others?) might benefit right now from an open thread on coping with acute romantic loss and heartbreak, for, you know, group support purposes and such. I know the subject has been dealt with in previous questions, and that moderating a thread is hardly zero work for you all, so if that’s not doable right now I understand. But I am also trying to exercise self care and ask for things that I think would help me this week! Thanks, lovely folks!

I am otherwise committed for the next few days, so moderation will be spotty, but if your feelings about a breakup are more about this song or this one than this one, this thread’s for you. Talk amongst yourselves and remember the Litany Against Fear.


Before we jump into sad, serious things, Gollum dreamed a dream (of coming to your party?) Courtesy of my friend @spyscribe. You guys watch The Lizzie Bennet Diaries, right?

Now, some letters about living situations gone bad (#451) and very, very bad (#452).

Dearest Captain,

I need some help with relationship ambivalence.

It’s been 3 years and we live together. This is going to sound awful, but I recently has the thought that I am better than him at almost everything. He is extremely unsure of himself and is very dependent on me. He needs help/frets about making even the tiniest decisions. His indecision about inconsequential things used to be something we joked about, but now I just feel very smothered. He often makes his problems/feelings my problem or responsibility. I have had the occasional moment of, “this is definitely right for me”, but more often I have had doubts about whether I really want to be with him.

Here’s the wrench: My whole life has been in a shake-up recently. In the past two weeks, I found out I am losing my job (a job I REALLY love), found out I didn’t get accepted into grad school, then, last week I witnessed a stranger’s death. I was one of the first people to stop and help him. I stood over him as he died, before medics even arrived. The experience has really had a profound effect on me. I was very disturbed by what happened. BF knew I had all this going on though that didn’t stop him from wanting to have a big relationship talk about feeling that we’ve been in a “rut” for the past week. This was two days after the stranger’s death. 

On one hand, I feel like I should not make any major life decisions in such a period of upheaval. On the other, I get the feeling I am being tested and have a gut feeling towards making changes in my life. 

I have a gut sense telling me to end it, but I can’t *rationalize*why because everything seems fine between us. He is a very kind person, intelligent, insightful, sweet, cute, great sense of humor and he loves me very much. We live together very harmoniously. On the downside, he has depression that he has never attempted to do anything about. Recently, on my urging, he agreed to talk to a psychiatrist and then asked me to give him the number to a psychiatrist. Later, he blamed me that he hadn’t called because I never gave him the number. This is the kind of responsibility-shifting that really upsets me and makes me sad. 

In my society, there is a slavish devotion to “rational” thinking and I doubt many of my intuitions. Then here I am being the one who is indecisive and generally at-sea!

I have no idea what to do and could use a little wisdom! 

Private Secretson

Dear Private Secretson:

Your vague gut feeling that you want to end it IS the reason.

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Dear Captain Awkward:

I’ve been with this guy for 2 years now. We had a falling out for about a month but we’ve been talking again since September. It’s been 4 months that we’re talking again and he’s afraid to make me his girlfrend because i messed up our relationship a little 2 years ago. We’re basically going out, we do everything we did when we were together, but its not official. He won’t let go of the past. At this New Years party we went to, he hung out with this other girl the entire night but claims nothing happened between them. He wants to make me his girlfriend now because im threatening to leave him. I dont know what to do, I’m hoping you can help me. Advice at least? I’m so lost.

Dear Lost,

The whole “You can’t be my official girlfriend because you did terrible, unforgivable things that I constantly bring up and blame you for, but I wish to keep enjoying your attentions and your…attentions” is one of the classic jerk-ploys. If whatever you supposedly “messed up” was so terrible that he doesn’t like you anymore, he wouldn’t hang around with you. If he still likes hanging around with you, then what you did can’t have been so terrible. This is a ploy to keep you around 100% on his terms, and dole out just enough affection and attention to keep you hooked and interested, but not enough to make you feel secure and happy and loved. And then, bonus! He gets to use your past to make you feel like everything is your fault. Manipulation 101.

If you really, really want to try one more time to make it work, say “Hey, if you’re interested in a casual relationship, that’s fine, but I’m not, so we should probably end this and let ourselves actually move on.” See what he says. If he brings up past-whatever-it-was, say “Hey, that was 2 years ago. I’ve apologized and done what I can to make amends. You either forgive me, in which case, don’t bring it up anymore, or you don’t, in which case, let’s end this. I can’t have that hanging over my head anymore.

Honestly, though, I don’t like this dude and I think you can do better than reward his shitty behavior or hold onto him with ultimatums. That’s my advice. “This isn’t working, and I want to break up. Let’s make it a clean break and not hang out or talk for a few months while we figure out how to move on. Happy New Year.

If you’re worried about backsliding into some kind of ummmmfriendship where everything stays confusing, the solution is simple:

  • Email: Block.
  • Facebook: Unfriend/block.
  • Twitter: Unfollow/block.
  • Cell phone: Block.

Do not unblock for at least three months.

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.



Dear Captain Awkward,

I have decided to end my 4-year relationship with my boyfriend. Throughout the last 4 years, despite my best efforts to convince myself, I have never been truly passionate and enthusiastic about this relationship, though we’ve definitely had some good moments. He on the other hand has been extremely invested in it. I have also recently had the opportunity to work abroad for a year, and had the chance to become independent and learn about myself and what I want for my life.

This, coupled with a long distance relationship that gave me the space to think, led to the realisation that, what I always felt to be a niggling sense of something being wrong, was that this relationship is not what I am looking for. I feel bored, unstimulated emotionally and intellectually, burdened, as well as extremely guilty and feeling like I am the worst girlfriend on earth. I feel that I have outgrown this relationship.

This is the first real relationship we’ve both had, and I know that it will not go down well with him at all. In fact he will probably fight tooth and nail to keep it going. This has happened before, on a previous occasion I tried to break up on. What happens is that he tries to convince me that I am in fact wrong about why I want to break up, and the issues I raise are things that “can be solved” and “we just have to work together”. If I were to tell him that, for example, the future I envision for myself is very different from his, he would counter with, “Oh that is not a problem, I can always change myself to suit you.” or “How would you know if you have not tried?”

The last time we went through this rigmarole, his arguments got me so upset and confused that I was unable to stand my ground and became a melting puddle of strong irrational emotions. I also felt compelled to say cruel things that are not really true, such as, “No I never loved you really, I was just convincing myself I did.” in order to not give him the ammunition to counter me with. All that made me so upset and miserable I went right back to him the next day.

So, Captain and Team Awkward, I need some advice on the following fronts:

1) How do I clarify my reasons for wanting to break up to myself, so that I am able to stand my ground and not melt into a puddle of emotions when he tries to counter me with his arguments?
2) Do you have suggestions on how I can get him to stop arguing about why I am wrong and he is right and we should not break up?
3) How can I tell him that sustaining a relationship is mutual, and you cannot just force someone to “work together” with you when they want out?

Please Let Me Go

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