Trying to come up with more interesting names for vagina. Bearded clam? Squish mitten? Actually, it’s trying to find the balance between bawdy and insightful. And trying to convince people to get over the inherent shame that’s been ingrained in us, about our bodies, about what’s “normal” sexually, etc.

A lot of sex writing I read is written like a pamphlet you’d get from your oral hygienist, which is informative, yes, but also a grade-A snoozefest. One of the things I often strive for is to make sex funny, because it is. Especially when you’re writing about things like Obama-shaped dildos.

What’s your most controversial article? And, why was it so?

I wrote an article for Queerky called Sci-fi or Outcry. Many people in the queer community were outraged about a short film called The Gendercator, saying it was trans-phobic, hateful, etc., except very few people had actually seen the movie (I was the only person who had formally reviewed the film, which may have changed since then).

The real reason people were up in arms and trying to get this film banned from the festival circuits was because of the filmmaker’s politics, not her (admittedly terrible, but not in an offensive way) short film.

I also happened to know the other filmmakers who were leading the charge against The Gendercator, having just interviewed them, so I was way more involved than I wanted to be. And I was amazed that the queer community, which is usually very inclusive, almost to a laughable extent, (as witnessed by the ever-growing acronym LGBTQQI…) was suddenly trying to censor something that many had never even seen.

If you were 3 search engine terms, what would they be?

“Mario Lopez” is consistently the top search engine term that leads people to my blog . The second is “is the apocalypse near?” The third is, “fucking ironic doesn’t it dude?” I realize these are literal answers but I feel that if Google says so, it’s probably true. 

How’d you get into freelance writing?

During a lapse of unemployment and in the middle of a huge break up, I suddenly had lots of time on my hands. So I went to Craigslist and browsed around the Missed Connections section, the ads for used coffee tables and then after I’d exhausted those, the writing gigs.

I started doing film reviews for The Aspect Ratio that way, even though I don’t really like movies, or watch them really, except over the holidays when my family tries to stave off the inevitable awkwardness of our togetherness by taking us to see Juno.

After I’d been doing that for a while, I got hooked up with Centerstage through my roommate at the time, who happened to know one of the editors. A little while later, I was bragging to that same editor about how I had just gotten a gig that would pay me to masturbate (reviewing sex toys for Early to Bed) and she asked me if I wanted to write a sex and dating column.

The moral of the story is to talk about masturbation with as many people as possible. 

What should people know about freelance writing before they start?

It really is about networking, which is quite cruel, considering the solitary nature of writing. But you’d be wise to get your ass out there and talk to people, everyone – even your mom’s dog sitter and the 16-year-old boy who sells empanadas on Ashland. You never know where a potential connection could come from. 

What are your future plans? Latest news?

I’m going to be a panelist for the Chicago History Museum’s sex series on April 22nd (from 7-8:30pm), to talk about online dating. I’m also going to be writing for the Chicago Tribune’s new blog/social networking site Chicago Now, which will launch May 1st. And I’m going to be writing about sex/relationships for Tonic News which is a do-gooder website.

And I’m in the process of trying to get the Red Eye to let me be their relationship columnist. Fingers crossed! 

What have you learned about Chicago through your writing?

That gay male leather bars are really quite charming. And that there are still some bar ATMs that dispense $10 bills. I’ve actually learned so much about Chicago through writing about it — it gets me out of the house.

If I weren’t writing about Chicago’s latest bar/TexMex restaurant/Naked Girls Reading event, I probably would have languished at home watching Buffy the Vampire Slayer and eating Tofutti Cuties.

How come you don’t have a blog?

One could argue that I have too many blogs. I don’t write in my main one often because I can’t quite draw that line between boring personal information about me and shameless self-promotion. I’m always going back and forth on whether to write about something, asking things like “Is this relevant? Does anyone care?” even if only 4 people are reading it. I apparently can’t just write for myself and the glory that is blogging. Not easily, anyway.

I also “write” for a pictorial blog called That’s Punny, and the now defunct Stuff Bisexuals Like . I twitter . I used to write for the Examiner , which is essentially a blog. There’s even a MySpace blog floating about that I refuse to delete for some unknown reason.  

When did you first consider yourself a writer?

I’ve never NOT considered myself a writer, which is weird because I’m incredibly fickle about pretty much everything else, and is probably why I’m bisexual. And why I use double negatives, even though I should know better. 

Tell me something people might not expect from you.

I won a $10 gift card at the talent show in high school for writing and performing a revenge song about my ex-boyfriend, who was also performing that night. 

What’s the biggest thing influencing your work?

I read promiscuously. It’s so inspiring to see the ways people shape words and ideas. I just started Audacia Ray’s “Naked on the Internet,” which is amazing. I’m a huge fan of Nerve (The Big Bang is my sex bible). Diablo Cody’s Candy Girl is fantastic. Salon.com, TheFrisky.com, Feministing, Gracethespot.com – I’m always on the lookout for new blogs to read in lieu of getting work done. 

What would you like to see change in the world of journalism/writing?

More representation by women, that’s for sure. I’d also like to see the online realm be less like the Wild West, with rampant online misogyny and general hate-fueled comments where people aren’t held accountable b/c of anonymity.

Feministing recently posted a great reference list of ways that women were taking back the internet . You should check it out. Of course, it does serve as a reminder that racism, sexism, bigotry are very much alive and well, despite the fact that we’re supposedly living in a “post-race” society. The Huffington Post recently called Lindsay Lohan and Sam Ronson as a post-gay couple. What? 

If you weren’t writing – what would you be doing?

Trying to get my mom to stop saying “expresso.” Oh, and bringing better educational options to Illinois families (http://www.incschools.org). 

Where you can find Anna:

• Anna’s website
• On Twitter
• Her blog