Will Miles Comedy

Comedy, women, and music. I do them all. I'm only good at one.


Me, @toasterwaffles, and @donnellrawlings at “The Morning AMp” on Vocalo Radio this morning…

Me, @toasterwaffles, and @donnellrawlings at “The Morning AMp” on Vocalo Radio this morning…

Taming the crowd at a fashion/art show. Fun times. Beautiful women

Taming the crowd at a fashion/art show. Fun times. Beautiful women

Sep 8th at 7AM / 0 notes
Worked with these two. Joey V and Felipe Esparza. Good work…

Worked with these two. Joey V and Felipe Esparza. Good work…

Me and Hannibal Buress during the work week…

Me and Hannibal Buress during the work week…

Sep 8th at 12AM / 0 notes
Work…. The good kind of work.

Work…. The good kind of work.

Lincoln Park: RedEye 'Hoods - The Party (Part 2: The after party) 

Aug 17th at 4PM / 0 notes

Part 2 of the story of me losing my virginity in a crowded party.  

Lincoln Park: RedEye 'Hoods - The Party (How to lose your virginity [Part 1]) 

Aug 15th at 3PM / 0 notes

My newest Red Eye Chicago blog about the first time I hit, smash and/or smanged someone in my life.  I would have put her name in here, but I think it was….

"I ain't sayin she a gold digger, I'm sayin I'm a gold digger" from the RedEye in Chicago 


A lot of people think I do stand up shows every night of the week so that I may one day be a nationally-recognized headlining comedian. This is only part of the story. One of my main goals in life is to find a woman who is much better off than me financially. Kanye West, fellow Chicagoan and Grammy-winning musician, had a great song a few years back titled “Gold Digger.” The song won many accolades and was praised for its great humor, in describing a woman who only dates men with money. However, he left out the fact that sometimes men date women for money just the same. I’ve done my own personal research, and figured out that I am one of those men.

I don’t exclusively date women with money, but that is due to my masculine nature. Being a man, I will also date just about anything with two legs and at least two breasts (look out, girl from “Total Recall”). Being out every night for a show, I don’t have time to figure out if a woman is rich right when I meet her, unless I have read about her financial situation on the internet previously (i.e. Paris Hilton). So I just date with the hopes that she will pick up dinner and the movie, and that will lead to true love.

Shows in Lincoln Park that I have done are my link to women who have inherited family wealth, women who are current divorcees, or women who are the headstrong self-made millionaires. I can meet them at Lincoln Hall concerts, Racine Plumbing comedy shows on Monday nights, and Stanley’s Kitchen & Tap comedy shows on Monday nights.

I recently did a show a Lincoln Hall with the group Afro-Zep, and from this show I have been contacted by a couple of women who are more than likely interested in doing business with me, but most importantly single, loaded, and interested in my story. This leads me to my next segment of this piece, how to attract the (wealthy) love of your life.


Whether you are an up and coming stand up comedian who just “needs a little support until Comedy Central calls him,” or the guy on the fast track to manager at Wendy’s, have a story a woman can believe in. Like it or not, we are all something to invest in. I make sure my stock is always on the rise, or that it at least looks that way.


My brother told me this phrase years ago concerning my career, but it works in dating, as well. I don’t go out to expensive restaurants in the beginning of my relationships with these rich women. I take them to my favorite taco spot in whatever neighborhood I am in. That way, I know I can pay if I have to. Then when she picks up that taco receipt, I know I’ve got her. By the fifth taco date, she’ll ask if she can pay for us to go to a nice restaurant for a change. That’s when the magic happens. But if you take any advice from this article, its always pay for the first two tacos. If you do that, you may never have to pay for a taco again.

And finally


My main goal for whenever I find the right woman is to raise a kid and live together forever, or at least that’s what I’ve been told. Either way, I make sure I’m not a complete asshole to the woman putting food in our future child’s mouth. If I can pick something up, I will do it with no argument. That way I’m more likely to get a higher allowance from my girl at a later date.

In conclusion, I really just always envisioned myself being a stay-at-home dad. Watch the kids during the day, go out and do stand up when they go to bed. Then by the time I get home, take them to school and get some sleep of my own. I am just looking for the right woman (with the right bank balance) to share that life.

Will Miles is a RedEye blogger.

"Ninja Roll" Article From The RedEye in Chicago 


When comedians hang out outside of a show, a lot of people think we talk about comedy for hours. While that is partially true, talking about comedy can only last for about ten minutes unless absolutely necessary. The rest of the time we are talking about how bad or good of a time we had with some woman or man we are currently attempting to date. This can lead to anything from the discovery of having dated the same person to the invention of a new term. It is in one of these post-show conversations that I first brought up the term, “The Ninja Roll.”

“The Ninja Roll,” as the Miles Urban Dictionary defines it, is: “1. noun, the stealth, covert escape from any awkward situation that a person may find themselves involved in, or 2. verb, to quickly and secretively escape from an awkward situation.”


I was meeting some friends at a bar in Lincoln Park called John Barleycorn. Normally, I date Wicker Park/ Bucktown/ South Loop girls, so I went to Barleycorn expecting to just continue drinking with friends and then eventually call it a night alone at my humble Ashland abode.

I got there and within ten minutes of meeting my friends, my tongue met the tongue of a nice young woman who knew my friends from their college days. After about ten minutes of inside-the-bar kissing and less than ten actual words spoken, we both decided that it would be better to get out of the dim lighting and into her apartment which was conveniently around the corner.

She had a very nice apartment based on the living room, which was as far as I made it. We moved our intense “talk” to her couch, which was when things started to get weird. Without a word uttered from my mouth, in the middle of everything, she whispered to me that “We can’t go any further.”

Being the gentleman that I am, I replied “No problem!” as I started to gather my things and head toward the exit.

After that, she pinned me back down, removed all of her garments, and said “You’re not going anywhere!” I shrieked. She then screamed for me to “put” things in “places.” I shrieked again. This banter went on for a few minutes with her constantly discussing (with herself) how we could and couldn’t do things at that very moment.

Finally, I nervously said, “No..you probably were right the first time. I should just go. I’ll definitely see you again.”

She said “Hell no! I want you now! I’m going to the bathroom to get ready. Don’t go anywhere…”

At this moment, I looked at my situation. Here we had a very nice woman, who I had spoken about 22 words to at that point, clearly confused about what she wanted from me. And I, a single young Black man in Lincoln Park, with a clean record of female partners up to that point, waiting alone on her couch. It was then that I remembered something I heard from my good friend and co-worker, Ariana. ”Sometimes you gotta just ninja roll outta there.” I wasn’t sure what it meant when she first told me, but it was then that I understood exactly what I had to do.

While my friend’s friend went to the bathroom, I perfected the “Ninja Roll.” I tucked myself into a ball, eased off of the couch, and somersaulted out of her front door onto a waiting Webster Avenue. I was out of there stealthily and covertly, and happily so.

The “Ninja Roll” doesn’t have to strictly be related to your dating situation, but it is a great way to get out of any awkward situation. I use it almost daily at work, home, and especially someone else’s home.

Will Miles is a RedEye blogger.

Will Miles On Twitter 

Mar 1st at 5PM / 0 notes

My twitter account…@mrwillmiles