“The Wingman” James Holeva and I “met” via Twitter. I checked out some info on him and thought he was a pretty sexy and interesting guy. Since I do have several male readers and really cool chick readers I knew that you guys would definitely want me to introduce you to this ladies man.
I’m so excited to have had the honor to interview this talented up-and-comer because I can assure you in no time at all he will be walking the red carpet, the next George Clooney, with a different hottie on his arm at every event.
While I have aspirations of walking the red carpet, see I Owe It All To Poop, I would never be the girl on “The Wingman’s” arm because let’s just face it, I’m totally not cool enough. And I’ve never been titty-f*cked and don’t think I’d ever want to be. It sounds painful. Does that make me a prude?
Well, don’t read on if you are a prude because this interview is Rated R. For those of you interested in testing your sexual prowess keep reading….and for my Chi-town readers “The Wingman” is having a live show this weekend — flyer below!
What made you decide to not only write but to publish The Wingman Chronicles?
I figured it would get me a lot of ass, and make me a lot of money, and ass and money are what life is about. Relax I’m half-joking. Honestly I heard about Sex and the City when I was in high school and I thought how cool would it be to read something like that but from the guy’s perspective. I looked everywhere for something like that but couldn’t find it, so I had to write it myself. I always felt my life was a movie, show, book etc. and write what I know. I remember I had an English teacher Mrs. Kelleher in high school and her saying to the class about writers and fiction, and how nobody’s life is that interesting, and raising my hands and telling her my life is, and she said, you should write about it. And I was like, I have been. I don’t think she knew at the time it would be quite as filthy but like I said, I write what I know, and I write it the way I’d want to read it.
How long did it take you to recount your sex-capades in your autobiography? Were there any stories you just couldn’t share or did you really put it all out there?
Well like they say in music you have your whole life to write your first album so it was a situation of that. I’m a fast writer but the first story of the book was written in August of 2008, and then I would write a story here and there, then in September of 2009 I started writing a column called The Wingman Chronicles for Northeastern PA. arts & entertainment weekly The Weekender so I compiled a lot of ideas I drew from there, then kept going. It was on and off while I was working on many other things but the actual spurts of writing were very quick. Recounting the stories is easy—one thing I have going for me is although I may pretend I don’t know a lot of girls I don’t want to talk to I actually remember just about everything I’ve experienced, and I’m talking about exact conversations, what was said, how the word was said, and this goes back to being a little kid. It’s not an autobiography, it’s an autobiographical novel so there is some fiction thrown in. I originally was going to go the memoir route until the last minute but I planned for this to be a series and had some fictional ideas for the future books so I wanted to keep my options opened creatively. The book is 90 percent completely true, and the other 10 percent based on true experiences and true feelings, with some fiction mixed in. A lot of the stuff the reader will be like “this is so fucked up, this can’t be true,” it probably is true, and some of the fictional parts are actually the most personal to me. I pretty much put it all out there, and the next book will go deeper.
How do women respond to you knowing you may write about your adventures with them? How do you handle any criticism?
They go out of their way to try to do crazy shit that will get them in the book. All I could say is stay the fuck away from my ass, and stop trying to pee on me. As for criticism I used to let it get to me but I’ve learned you can’t please everybody, and when you do this kind of work any reaction is good reaction. So it’s a combination of ignoring and taking every chance I get to call a cunt a cunt. I think all the kids out there should do the same thing.
You created and star in “The Wingman” a TV pilot currently being shopped to networks…maybe the next Sex and the City? How do you like acting?
Yes, I see it as a male version in many ways, and I see it being very close to the book. In fact, I wanted the book to feel like the reader is watching a show on DVD or Netflix and the chapters to be like episodes. You could watch, in this case read, one episode at a time, or a few, or go right through the whole season like I do when I find a new show I like. I love acting, and have always wanted to act. In fact, while writing I get up and act the dialogue out to make sure it feels right.
Check out the trailer for the pilot here.
Which actress would you love to work with?
A couple who pop out are Scarlett Johansson, who I see as perfect for the Noelle character from the book, and Gina Gershon who would be great to play a character in the sequel.
Gina Gershon
You also have a debut album coming out and a radio show! How do you do it all and what do you envision for your future?
I recorded a comedy album last year, and it should be out soon. It’s going to be called “Bedrooms, Backseats and Bathroom Stalls.” The recording went awesome and really has the live experience I try to give in my shows, and wanted it to have. I think sometimes albums come off very rehearsed but my show is very interactive and crazy, I do a lot of crowd work, I do the #askwingman Q & A portion of the show where I answer sex, dating, relationship and creepin’ questions on-stage and I wanted that live energy to really come out and I think we got that. I did a syndicated weekly radio segment “Wingman Wednesday” originating on 97 BHT from 2008-2011 and that was a blast. I had to be toned down since it was a top 40 section but it went very well, and I’d answer dating and creepin’ questions every week. I’m hustling constantly and always have a ton of ideas going on. And more than half the time is spent on the business end of it all but it’s what it takes. I envision myself of course writing and starring in my own TV series, writing and starring in movies… comedy/drama, doing great work, more of The Wingman Chronicles book series, writing other books of other genres, world tour, playing Madison Square Garden, and also have other TV series and scripts… Both for me to act in, and stuff I wrote with other people in mind. And in the short term keep writing, and touring, trying to go everywhere. My book is doing well all over the world and I want all my fans to have the chance to come see me live. Yeah, I have a few plans.
Let’s talk breasts since you’ve seen a lot….big, small? Real, fake? How’s your motorboat skills?
I don’t like real tits, I don’t like fake tits, I like great tits. How they got that way is none of my concern. I don’t order dinner at a restaurant and go into the kitchen and ask the chef. What exactly did you put in this sauce, are the spices natural, is it gluten free? I just slop that up. Same with tits, which is why my motorboat skills are top notch. It’s all about the passion and the nipple sucking. However having a huge cock and all I do prefer to titty-fuck. The best part about it is keeping a girl in suspense about where I’ll blow my load.
Do you have a background in journalism/writing/communications? What would you be doing if you weren’t starting a “Wingman” brand?
Yes I do. I was a journalist for six years writing primarily sports features but a little bit of everything, from game stories, to entertainment, and some hard news. I also had a ski column “The White Stuff” (and no, I didn’t even name it), before I had my sex column “The Wingman Chronicles.” Hmm… If I wasn’t starting “The Wingman” brand I’d be working on another writing, acting or comedy related project but otherwise I’d be pursuing journalism actively or working in marketing/public relations… If it was something completely different I’d be a lawyer. You’ll see in my book I have a solid legal background, learned primarily from watching Ally McBeal and Boston Legal.
Being a native to New York I’m sure you’ve been to The Sex Museum? What was your favorite exhibit?
I’m actually a native to Clarks Summit, PA, but live in New York City now. My favorite exhibit would have to be the bathroom. Me, sex museum, horny girls… I kind of was the exhibit. Don’t worry I’m thinking about merchandising replica hard-eights.
What is your drink of choice?
Diet coke… I live on that. Alcoholic drinks is what I’m sure you actually mean and lately either Vodka Tonic or Vodka Cranberry. I used to be big into Sugar Free Red Bull and Vodka but lately the majority of my drinking is at shows, a little bit before and during, and then primarily after and I’m already amped enough from the performance so I don’t need more caffeine.
Who is your favorite sports team? Be careful…you’re talking to a lifelong Cubs fan!
Well I’m more about watching a good game in general. Baseball is by far my favorite sport to watch, but I would have to say the Phillies.
Any words of wisdom for Jlee’s readers?
Read my book, come see me live, follow me on twitter… If you’re a hot girl let me spank you on-stage, sign your tits and ass. Don’t use an endless amount of coupons in line in front of me at the grocery store. Every time you cockblock you’re not helping your friends, you’re making them hate you, and most of all don’t ever let anybody stifle your adventure.
Live in Chicago January 11th and 12th! Get your tickets!
Please follow “The Wingman” via twitter or you can ‘Like’ his FB page here. A big thank you to Mr. James Holeva! This interview has been a pleasure. I’ve been laughing and cringing. 
Thanks again.
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