Tag Archives: The Darth Vader Boyfriend

Hello Captain Awkward,

I’m feeling quite stuck in a romantic situation and am hoping you can help.

Last year I took a job in a town 5 hours away. To my surprise and delight, a co-worker who I had a secret crush on messaged me daily after I left and from there she admits she is attracted to me. Problem being, she is married. The texting gets intense- sexting 24/7. After a few weeks, I drove up to the city and we spent the weekend with each other, in bed together for most of it. She was racked with guilt, I felt guilty too and also guilty because I had feelings for her and she insisted no feelings were to be involved in this. Guilty feelings made way for more and more of these weekends and trips together- we saw each other most weeks despite living in different cities, having an intensely passionate and sexual relationship for over a year.

I didn’t want to sneak around forever and wanted more of a relationship. She told me for months that we would have that, and she was in the process of separating. However one day she announces she can never leave him and get a divorce. Also, she doesn’t want to disappoint and be disowned by friends and family. I was upset but carried on with the relationship because I just didn’t have it in me to leave.

Before we got together, she had planned to live overseas and travel. I would get upset as the time loomed closer when she was due to leave, just as we were getting serious. She reassured me that it was for the best- a way of separating from her husband so we could together. Yet, only a week before she left, she informed me that he had taken a job over there and was going with her. Nevertheless, she insists they aren’t really together, just friends and she will come back to be with me in a year’s time.

I was upset and angry, although accepting that I am ultimately responsible for my own unhappiness about it because I did get involved with a married woman.

I am still in love with her and want to be with her. However I know it’s best for me to leave this all behind. Yet every time I do, she guilt trips me so hard into staying and staying in contact while she is over there- making it impossible to move on. I was hoping Captain that you would be able to shed some light on an escape route out of this and some potential scripts for when she guilts me into staying.

Thanks heaps,


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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 & Army,

About a month ago, I finally broke things off with a long-term Darth Vader ex I’ll call Joe. We officially broke up last year, but spent this summer falling in love all over again, though we kept it completely secret. However, when Joe finally admitted to cheating on me with a very close friend while we were still together – something I had long suspected but never had confirmed, and which he had directly lied to me about many times – I knew it had to be over, once and for all. So, despite Joe’s protestations and pleas, I told him not to contact me ever again, and after a few days of mourning (and not reaching out, despite wanting to very badly) found the courage to block him in every way possible. Only in the last week was I finally starting to feel something more than the emotional mess that is equal parts angry, sad and nostalgic.

But then, just yesterday, I got a call from another ex, someone I briefly dated just a few months before Joe and I resumed our relationship. The ex told me they were recently tested for STIs, and came up positive for a common one. I immediately made an appointment for myself, and am now waiting for results to come back.

Of course, I know that if the test comes back positive that I will have to tell Joe. But I’m already worrying about having any contact with this person again, who I have finally removed completely from my life and who was a 100% toxic influence. I feel that news like this merits a phone call, but the thought of even hearing Joe’s voice again fills me with sadness, dread and, if I’m totally honest, excitement. I worry that I won’t be able to keep the conversation to simply the facts of the situation, and that if I open that doorway right now, I won’t be emotionally able to shut it again. My only friend who knows about our summer fling suggested writing an e-mail, and then keeping Joe’s blocked so he can’t respond. But I feel like that is somehow wrong, considering this is an issue of sexual health and safety.

What do you think, Captain? Should I call, or will an e-mail suffice? And either way, how do I make sure to stay to the script? Is there a good script for this?

Possibly Positive

Dear Possibly Positive:

Would you believe that there are greeting cards for just this occasion? And that there are services where you can send this info anonymously (recommended!)? And that there’s a very sweet show on Netflix called “Scrotal Recall” about just this problem if you’d like to feel less alone about the whole thing?

You do not have to have a talk with “Joe” about this, LW, and you don’t owe him and the “close friend” he was sleeping with anything but the basic information to protect their health. If you choose not to use InSPOT, an email (DEFINITELY EMAIL OR POSTAL MAIL, NO PHONE OR MEETING UP) script might go like this:

“Dear Joe/Dear Friend:

One of my former sex partners tested positive for _______ STI, and given the timing you may have been exposed, too. Please get tested and inform your partners.”


“I recently tested positive for _______ STI, and I recommend that you get tested and inform recent sex partners as well.”

Informing them takes care of your ethical responsibilities here. I do think you should reach out to the friend as well (Do you honestly trust Joe to take care of someone else’s health in an ethical way?) Once you convey the info, you don’t need to have one iota more discussion or provide any more details.You can safely ignore/block any replies. You do not have to listen to Joe’s reactions or care about his feelings right now. Pesky microbes are not a referendum on you or on your past relationships, and reaching out with key health information is one good exception for violating a “no contact” policy.

I hope you get answers soon and that they alleviate your anxiety. When you climb back on the dating horse, this might help.

P.S. There’s always singing telegrams!

My friend and Agony Aunt colleague Robin “Miss Conduct” Abrahams has written an excellent piece that combines two of my favorite things: Better Caul Saul and boundaries. Kim Wexler, a character on the show, is a master of boundaries and you don’t have to watch to appreciate the piece.

Piny linked me to this great piece from Heather Havrilesky, “Can I trust my judgment around men?” It’s very relevant to our discussions of the
Darth Vader partner and how they come on so strong and magically at the beginning (bolding mine):

When you meet someone who’s charming and very intense and he immediately starts talking about long-term goals for love and marriage and kids, that’s a seductive thing. In my experience, that kind of intense talk can actually be a sign of trouble, a sign that the guy is trying to quickly correct all the mistakes of the past and award himself a “happily ever after” without knowing much about the person in front of him. The one time I met someone who talked this way, it was hard not to get caught up in it. So this is how it feels to finally meet The One! I thought. You both just know, immediately, that you’re meant for each other! After years of encountering caution and hesitation from dates and even boyfriends, I was thrilled to find someone who could recognize in an instant HOW GREAT I WAS.

Even once I discovered that he was newly separated and still reeling from his wife’s sudden exit, I didn’t give up. I didn’t recognize that he was handling his sadness by escaping into something new, something that HAD to lead to marriage to make up for what he’d just lost. Looking back, I can’t believe I could be so dumb. But at that point, I had never experienced that kind of confident intensity from a man. He was also older than me. After years of dating one man-child after another, I thought I was meeting a mature adult male for the first time.

Hello, 31-year-old me staying up all night on the phone with some guy who talked really big. Hello younger versions some of you, too. Jedi Hugs to our younger selves, and to our older, wiser selves.

There is a Washington, D.C. Meetup in the works for April 26. Details:

Washington, DC Meetup

Rubymendez and Flightless have arranged an event in DC.

Time/place: Sunday, 5pm April 26th at Dupont Circle’s THE BOARD ROOM (

They serve happy-hour-priced drinks from 5-7pm on Sundays, with board games for rent — EVERY board game you can think of! They don’t serve food, but they allow you to bring in food, or get it delivered, so hopefully all dietary needs can be accommodated. For instance, you could grab empanadas from Julia’s down the street and bring them over (we will have some bites to share!)

To find us: rubymendez will be wearing a rainbow winter hat; flightless has blue hair and will be wearing a railway conductor’s hat. Feel free to rock your own hats, rainbows, or zany garb! We’ll also have stickers or blank nametags you can customize as desired.

You can post on our DC Meetup thread in the forums if you have questions.

FEELINGSNOTE: I MISS D.C. IN SPRINGTIME AND JULIA’S EMPANADAS. Have the best time. If you’re in Chicago and you did your taxes already stop by the Awkward Meet & Geek tomorrow at Geek Bar anytime between 6 and 10 pm and say hello. I’m also reading at That’s All She Wrote on Sunday night, April 19, Great Lakes Tattoo, 8 pm, BYOB/Free admission.

Finally, we have traced the creator of the Riding-The-Nopetepus gif if you wish to marvel at its glory:

Animated gif of a girl riding an octopus and saying "nope!"

Gandalf & Darth Vader

Who would win in a fight? A common question posed by The Internet.

Hello, Citizens of Friday.

First order of business, this great nod of solidarity for the socially awkward from Dorothy Parker.

‎”Those who have mastered etiquette, who are entirely, impeccably right, would seem to arrive at a point of exquisite dullness.” –Dorothy Parker

Second order of business: This great post from The Pervocracy, “How To Have Sex on Purpose.” It’s an essay form of the talk about consent and what people can learn about sex from kinksters that Cliff gave at U of Chicago’s Sex Week last week.

Third order of business: Great Darth Vader Boyfriend song or GREATEST Darth Vader Boyfriend song?

That should segue us nicely into this question:

Dear Captain Awkward:

My best friend at work is romantically obsessed with her douche of a boyfriend. He has been both mentally and sexually manipulative and verbally abusive. All of her friends at work realized this. We were asked on many occasions for advice by her or listened to her vent, but she only tightens her grip on him, and increasingly pushes her own friends away. Any advice? Is she a lost cause?


Don Draper

Dear Don:

Your selected username is pretty unintentionally funny, because Don Draper is TOTALLY a Darth Vader Boyfriend. He physically assaults Betty, and tried to convince her that she cannot leave him. He totally broods his way into getting sympathy sex with ladies who he does not treat very well.

Silhouette of Darth Vader replaces Draper in Mad Men opening credit sequence.

Awesome design by Dann Matthews.. P.S. There are T-shirts.

Don’t know how long you’ve been reading, but we covered Darths at length in one of the first-ever posts on this blog. And we also covered how to tell a friend that you have had enough venting for the time being.

The points I’d reiterate here is:

  • Your friend does not have to break up with her boyfriend to please you. Even if he sucks. That’s just not how people and their hearts work.
  • But also, you do not have to endlessly listen to her talk about him. Her sun may rise and set by the cycle of her bad boyfriend’s moods and behaviors, but yours does not have to.

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Darth Vader beckoning to Luke in Empire Strikes Back.

“Everything’s more dramatic and exciting on the Dark Side of the Force!”

Before we dig into today’s letter, I really like this “Ask Polly” piece at The Awl, I Miss My Maniac Ex. The Maniac Ex is what we around these parts would call a Darth Vader boyfriend.

So you focus on that one magical night, in the middle of a sea of terrible nights, where he held your hand and treated you like a person and you drank too much and that awesome song was playing and you imagined, in that moment, that you two were destined to be together forever, and your whole life might be this good. Lucky for you, your whole life turned out even better than that, it just doesn’t feel like it because you’ve become acclimated to love the way you used to be acclimated to suffering. Those highs you miss are the sorts of highs that occur in a life mostly made up of lows.

There are plenty of different kinds of bad partners. A Darth Vader, to me, is one who strings you along with tiny bits of your heart’s desire at carefully controlled intervals. Not enough to actually sustain you, but enough to keep you hooked. Enough to make you abdicate everything you know about what’s good for you.

Her advice about how to refocus these pangs and get past it is quite good.

Today’s letter, the first to come into the new inbox, is also about exes and regretting the past.

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Hello! I took a few days off to work at my real job and go to the movies and read books and hang out with my boyfriend. It was awesome and I will be doing more of that + shooting a short film in August.

Old business: If you donated to the pledge drive via the Dwolla link, I don’t have your email address. So email me and I’ll send you the link to the movie. Also, a few of the PayPal donors had email addresses that bounced back (or I may have missed you), so if you are missing the movie let me know and I will fix that ASAP.

New business:

Attention: The Foster Kitten Cam has new kitties.

Also, this is a very sad letter. I am putting it behind a cut. And I want to say something very clearly first:

This blogger is officially, unilaterally, and forever pro-choice. I believe the decision to terminate a pregnancy is morally neutral and should be private, legal & safe. I trust that anyone undertaking that decision has their own reasons that are better than anything I or any outside party could come up with. I will be moderating comments here accordingly. You can disagree with me…privately in your heart. Or on other websites. All anti-choice lobbying & debate will be deleted without warning. Repeat offenders will be banned without warning. This was your warning. If this is a hot-button issue for you and you don’t think you’ll be able to resist internet-fighting what you see as the Good Fight for Tiny Innocent Babies, maybe don’t click further. You will not change my mind, and this is not the place to try out your Ethics 101 arguments. The Letter Writer and I are not interested in your jibber-jabber.

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