Jennifer Peepas is Captain Awkward is Our Newest Geek of the Week
Recently I visted former Geek of the Week, Randy Chertkow in Chicago for his big birthday bash, RandyCon. Having the good fortune to arrive early and spend a couple of days with Randy, doing all the things Randy loves – namely eating and ….well, eating – I found myself on the receiving end of some great advice about candidates for Geek of the Week.
“Oh,” he exclaimed over Mongolian Barbeque, “You have to check out my friend Jen’s site, Captain Awkward. She writes an advice column using geeky references for many of her answers. You’d love her.” He was right.
Jennifer Peepas had me at the Category Cloud in the right-hand column of CaptainAwkward.com. Darth Vader Boyfriend, Overthinking It, How to Say No, and the mysterious The Book of the Face are just the beginning of the intriguing categories listed. Just below the cloud, in her list of recent posts, are titles that imply a bit of cheek like, “How do I reclaim my awesomeness” and “Gender-Policing Grandmas,” as well as ones with more somber tones like, “How do I help my boyfriend when he won’t ask for help,” and “How do I tell people about my divorce?”
In short, Captain Awkward had so much awesome in just the right hand column that I knew instantly we absolutely must get this woman to agree to an interview. But first, I spent the better part of my afternoon reading one piece of advice after another. Once you click on a Darth Vader Boyfriend tab, you pretty much can kiss the rest of your day goodbye. In post #184, Confusing Dude is Confusing, Jennifer explains the concept to one letter-writer:
I think he is your Darth Vader boyfriend; all wounded and complicated and sexy and trying to manipulate your emotions so that you will always see him in a positive light even when he does massively fucked up things.
“Ahhhh,” I thought, “that guy. Yes, I’ve dated that guy.” We’ve all dated that guy, haven’t we? I was hooked. I read post after post, alternately laughing, yelling out things that no white girl should like, “preach!” and things no one over 30 should like, “hollaaaah!” until I finally took a break to send an e-mail requesting an interview. Luckily, Jennifer graciously agreed so quickly I did not have to go into full-blown fan-girl mode and hound her until she consented.
Here are the results.
1. Every geek has an origin story. What started you down the path to advice columnist?
I think the first seed of the idea came years ago, when I was in grad school and brainstorming ideas for earning money. I wrote down “Set up roving advice booth like Peanuts in downtown Chicago?” in the margins of some notebook. (I still might do that, actually).
But really, like any creative venture, it was a big messy convergence of things. I teach filmmaking to college freshmen, and I was doing a lot of work in class around the people-skills needed to collaborate with others which often includes disagreeing strongly about the creative direction of a project in a constructive way. I’ve always read advice columns – they make great source material for dramatic stories because they are full of conflict – and I realized that I had a lot to say about learning how to speak up for yourself. I love filmmaking, but it’s so expensive and time-consuming and I wanted to find a more immediate way to connect with an audience where I didn’t have to worry about structure or censoring myself. All of this was swirling around in my head one day in early 2011, then I went out to brunch with some of my closest friends and said, “Hey, I’m thinking about maybe doing this thing?” and they said “DO THE THING” and I’m pretty sure we bought the domain the next day.
2. You have answered a lot of letters – which one or two would you consider the most successful? – i.e. you are totally satisfied with the advice you gave, or the writer let you know later how much you helped them.
One of the most-read and linked posts is “A Shy Guy Caught My Eye.” It has really set the foundation for all of the posts about love and dating, especially Geek dating, on the site. I feel lucky that it’s the kind of place where the letter writers feel comfortable coming back and letting us know how things went, and was overjoyed to see that the guy who wrote this letter is now happily kissing a lady or ladies. One of my personal favorite posts is The Golden Retriever/Kwisatz Haderach of Love. A few months after I wrote it I broke up with my long-term partner and it was a good reminder to myself that I knew how to get through this even when it didn’t feel like I would. Plus, Dune references bring all the boys to the yard.
3. Any advice you would take back now, or change if you could?
The good news is that I write pretty quickly and don’t self-censor or filter very much. That’s also the bad news, so there are certainly things that are sloppy or overly harsh. I get told that I push therapy too much and am too quick to tell people to dump irritating friends and partners when, if you’re the one in the situation, it’s not that easy.
4. What is the biggest struggle running your site?
One obvious challenge is finding the time. I will probably never be able to answer all the questions I receive so I have to be somewhat ruthless about choosing. On the plus side, it means I won’t run out of material.
Early this year there was a very sad and scary patch where young people were writing to me about horrifically abusive home situations and serious depression – one had gone so far as to start composing suicide notes and wanted my input on wording them. I’m not a trained mental health professional of any stripe, and I don’t have power to intervene beyond saying “Please, please call someone, here, I Googled some numbers for you, also, don’t kill yourself.” It was very stressful and scary for me to feel that much responsibility for other people, and there was some soul-searching about what I really wanted to do and was realistically equipped to do with the site.
5. Do you find yourself getting asked for advice from friends, much like doctors get cornered with questions about strange growths or flu-like symptoms?
Not really…? Or at least, not inappropriately, unlike the aspiring screenwriter who thought I might want to give his feature script a once-over on our first (and only) date a few months back. My friends have been really supportive of me and the site up to and including writing guest-posts themselves, and if anyone can distinguish between Captain Awkward, Advice Giver and Jennifer, Disheveled Nerd, it’s them. I’m probably way more likely to expound on something they *didn’t* ask for help with.
There was a moment a few months back where I did something unthinkingly jerky and a friend (who is an avid reader) wrote me a very kind but firm email asking me to apologize and to not do that again. I felt a weird mix of mortification at my jerky behavior and pride that hey, she’s using her words when maybe she would not have before and our relationship could be better for that.
6. What geeky shows, comics, movies or books make your “You GOTTA see this” list? Any guilty pleasures you feel like confessing?
Does geekiness stem from the genre/offbeatness/geek culture cred of the thing you like or the avid love you have for the thing? My favorite thing on television recently is Sherlock. I probably watched all of the episodes in the second season three or four times. I’m also mainlining Mad Men and enjoying all the fun that the writers are having with Game of Thrones. I love Kate Beaton’s webcomics, the website A Softer World and the website The Adventures of Awkward Black Girl. I really liked The Avengers, especially Mark Ruffalo’s performance as The Hulk. Some friends and I are going to re-read some of the old Stephen King books that creeped us out as children this summer, starting with IT. That’s not a guilty pleasure, that’s a “I still can’t walk over sewer grates without flinching and sometimes I check behind the shower curtains for clowns when I’m in strange houses” pleasure.**
A big hearty thank you to Jennifer Peepas for her time and her thoughtful answers. It is clear that while she has a lot of fun with her site, she also takes herself, her writing and her readers seriously. Randy was right – I love her site and admire her wit and intelligence. I also have tremendous respect for anyone who is a proponent of the “use your words” approach to friendship and love. Preach!
Please, please check out her out when you get a chance.
**Yes, it does seem like Jennifer and I are sisters from another mother…which admittedly doesn’t work as well as if we were brothers, for sake of rhyming. Click the following for the Stephen King post I wrote, the Game of Thrones post, and the whole Avengers Boot Camp thing. Seriously, we may have been separated at birth.

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[...] In linkmania and internet fame news, Proffitt from Good Girls Gone Geek interviews me about this here site today. [...]
How about sisters from a different mister?
I really like Captain Awkward aka Jen, and this interview was an interesting read!
I was going to suggest the mister but it doesn’t really rule out having the same mother. Oh well. I too am a fan of Cpt. Awkward!
Ahhh, I should have thought of that!
Yes! Captain Awkward kickes motherfucken asse!!!11!1!!!11!