It Takes Balls: Dating Single Moms and Other Confessions from an Unprepared Single Dad

It Takes Balls: Dating Single Moms and Other Confessions from an Unprepared Single Dad

by Josh Wolf


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Josh Wolf—one of the stars and writers of Chelsea Lately and After Lately —delivers a hilarious collection of essays that reminds us all what it takes to conquer fatherhood without sacrificing manhood.

Struggling to make it as a stand-up comic didn't always fit with being a single parent. But Josh figured out his own set of rules—through trial and (frequent) error. Early picking up kids from school? The nearby strip club is a great place to kill time and bond with some like-minded dads. Want a drunken heart-to-heart with your son? First make sure there's no Sharpie around in case you pass out. Wondering where to take that special someone at the end of the night's Remember that no sane woman will have sex with you in a one-bedroom apartment where your kids are sleeping—even if you promise to be really, really quiet.

Whether it's revealing the secrets to limitless hookups (hint: it's single moms) and getting rid of your children's friends that you just can't stand (hint: it's not single moms), or blackmailing PTA members and ignoring health codes, Josh is sure to impart some parenting wisdom along the way. Or at least have a good time trying.

Product Details

ISBN-13: 9781455511679
Publisher: Grand Central Publishing
Publication date: 03/19/2013
Pages: 256
Sales rank: 835,654
Product dimensions: 5.70(w) x 8.30(h) x 1.10(d)

About the Author

A stand-up comic for thirteen years, Josh Wolf has toured with Larry the Cable Guy, Chelsea Handler, and "the Comedians of Chelsea Lately." His television work includes recurring roles on NBC's My Name Is Earl, and Fox's Raising Hope. He has also hosted two seasons of the Fox Sports online series "The College Experiment." He's currently a regular writer/performer on the E! hit series Chelsea Lately, and was a regular on the spin-off, After Lately.

Read an Excerpt

It Takes Balls

Dating Single Moms and Other Confessions from an Unprepared Single Dad

By Josh Wolf

Grand Central Publishing

Copyright © 2013 Josh Wolf
All rights reserved.
ISBN: 978-1-4555-1167-9


Single Mothers

Single mothers are pretty damn good in bed.

You heard me.

Pretty. Damn. Good.

I mean, it makes sense, doesn't it? They've been cooped up in a house with kids all day, having no grownup discussions, sometimes not even speaking in full sentences, making lunches, doing homework, going shopping ... basically doing everything. So, when they finally put the kids asleep and have a few hours before they pass out completely exhausted, they are ready to release some pent-up frustration.

Let me introduce myself. My name is Pent-Up Frustration. Pleased to meet you.

Or it was anyway. I went through a period there where the only people I was dating were single moms. Hell, I was a single father, so it made sense but the problem was that I was still young enough where I didn't want to just date breeders. As a matter of fact, I was actively trying to stay away from people with kids, but it just wasn't possible. The girls my age wanted nothing to do with a single guy with three hangers-on. Shocker. But the moms? A single dad, who was a little bit broken but still responsible enough to take care of three kids by himself? It made those women looser than if they'd had two Vicodin and a Soma. The one thing I learned fast about single moms was that because of drama with their ex, kids' schedules, and life, getting involved with them was a roller coaster with lots of rules and regulations. Sex, however, was always good and they were always up for a roll around as long as it fit into the schedule. I remember one woman who told me to be at her house at 9:10 because she put the kids down at 8:45. I would walk in, and she literally had a comforter down on the floor no more than five feet away from the front door. She said there was no need for me to go any farther into her home. She lined up three bottles of water by the comforter so I didn't have to go into the kitchen and there was a bathroom five feet from our makeshift love nest. She wanted to be in bed with the lights out by 10:15. No talking wanted, and cuddling was not an option. It was truly romance at its finest. Not gonna lie, she scared me a little.

Not gonna lie, I also liked it. I liked it a lot.

It was really an interesting experience for me being a single dad. At first, I had no idea what would happen or if I would ever get laid again. All I could think about was who in the world wants to sleep with a wannabe comedian with no job and three kids? Turns out, more people than I thought; they just weren't the people I was thinking of. I remember the first day I showed up to school after my ex and I split. It was hilarious. When I was with my ex, I would show up to school in the morning and all of the women were in sweatpants, no makeup, hair all jacked up—you know, the way people look in the morning when they roll out of bed and throw something on. Right after my ex and I split up, I showed up to school and I didn't recognize a bunch of the women because their makeup was perfect, their hair was teased and blow-dried, and they all looked like they were dressed to go out for a drink. Who were those women, you ask? The single moms. It was insane. For the first time in my life, I was being pursued in a big way and it was pretty freakin' awesome.

"I heard the news. I am so sorry. Do you want to go out for coffee and talk about it?"

And ...

"It's just so sad. I've been through exactly what you're going through. What you need is a nice home-cooked meal."

And ...

"My door is always open for you. I mean that. Always open ... day or night."

It was crazy. I felt like a free agent baseball player who everyone wanted on their team. There was one particular woman who was absolutely insane. She was a very attractive black woman, who was always drunk. Always. She read to our kids' kindergarten class one day completely hammered. She was reading, "'One fish, two fish, red fish, blue fish'" and slurred her way through all of it. The best part is that she gave a running drunk commentary as she read the book. She'd say things like, "'Here are some who like to run. They run for fun in the hot, hot sun.' Ugh. Run in the sun? Who does that shit? You get all swampy." Her ex-husband was some bigwig, so she had tons of dough and absolutely no reason to ever work or do anything productive. She literally, no exaggeration, would see women talking to me (this is at 8 am, mind you), walk up, grab my Johnson, and say things like, "You ready for this black bitch?"


Don't get me wrong, I was really fuckin' turned on by it, and that worked every time she did it, but the frenzy was something I couldn't understand. When I was single without kids, I didn't have near this amount of success. Not even close. But now, no job, no money, driving a minivan with three kids in the back, I get rich chicks walking up to me and grabbing my dick at an elementary school. It didn't make any sense. For some of those ladies, when I drove up to school with three kids in the back of my Toyota Sienna I could almost hear vaginas starting to hum. (Not sure what that means exactly but I sure enjoyed writing it.) It was time to readjust my game and try to get out there.

I don't want you thinking that I started sleeping with tons of women right when my ex and I broke up. I mean, I did, but it's not like our break-up was a shock to me, her, or anyone within one hundred miles of us. Our relationship had run its course long before we actually broke up so the actual split was just a formality. I think one of the reasons I stayed in the relationship for so long was that I didn't think there was any way in hell that anyone else would go out with me (see above reasons). The other reason was that I was scared out of my fucking mind to raise three kids by myself. I still felt like a kid myself. Shit, I still jerked off into a sock. People who masturbate into socks shouldn't be in charge of other people's lives.

Getting back out there was going to be a challenge for myriad reasons. I know some of you are thinking, "There must have been some times when you didn't have to go out with a parent, right? There had to be some young'un who was willing to share the wealth." Nope. I had some serious limitations that made me have to find creative ways to work around them and that meant I had to start living by a few rules myself.

Rule number one: There clearly wasn't going to be any sex happening at my place. My kids and I all lived in a one-bedroom. Not that easy to bring a girl back to my place and be like, "(Whispering) Don't worry about them. They're real heavy sleepers. Wait ... where are you going? Don't go!" Not only was there no room, but I had decided I wasn't going to introduce my kids to anyone who I didn't think was going to be in their lives for a long time. On top of that, my apartment was a fucking disaster. It's so funny that apartments all over the country have these fancy, exotic-sounding names like Shangri La Apartments or Hollywood Treasure and inside they look like a place where people get murdered for crack. My place was no different and it was called The Luxury Apartments. Not gonna get a lot of va-jay-jay when you open the door to your place and it looks like a fucking sweatshop. There were kids crammed on the floor of my bedroom and clothes and toys thrown all over like an aisle at Marshalls. There was no way anyone would fuck me in that place, and if someone would have, it would have been very clear that that person had some serious problems.

Rule number two: I couldn't do anything that cost money because I had no more than $200 in my bank at any time and paid the bills catering Mexican food three times a week. I smelled like goat cheese quesadillas for two years of my life. I know this is going to sound like a statement made by Captain Obvious but having no money really limits what you can do. I hear people say they have no money, but I literally had nothing. I seriously could not afford to take someone to the movies. So the question then becomes, what else do you do? There are only so many times that someone will go hiking with you. Especially if you start insinuating that it might not be a bad place to visit later that night. (See Rule Number One to figure out why I was looking for an outdoor spot to have sex.) There are only so many times you can ask a girl out on a picnic. Ugh. Just typing that brings back memories that make my fucking skin crawl. I was always the guy who made fun of people and their picnics. "Oh, so sorry. Did my ball knock over your red plastic cups that you brought out for your ridiculous fucking picnic?" There was something so emasculating about them. And uncomfortable. Holy shit. The worst. The absolute fucking worst. I had to do it though because it was easily disguised as romantic and thoughtful. Also, another place to insinuate we should go back to later that night. (Again, see Rule Number One.) I actually did get a girl to meet me back at the picnic spot for some outdoor sex one night. Couldn't believe it. At the picnic, she had said, "This is really romantic. I love picnics. I also really like lying on a blanket and looking at the stars."

Uh ... me, too. I like that, too.

We decided to meet later that night. Same spot. I was bringing the blanket and she was bringing the vagina. I don't think that's exactly what we said when we made the plans but I'm pretty sure it was understood. I got there before she did to clean out the ground underneath the blanket. The last thing I wanted was a stick or a rock jabbing either one of us in the ass or leg and derailing the fun train. I also wanted to make sure we weren't too visible. I desperately wanted to get laid but I couldn't get arrested for it. That would have been no bueno. She showed up wearing a sweater, a pair of jeans, and carrying a bottle of wine. Personally, I would have gone with a skirt if I were her because the skirt never really needs to come off and if shit goes down you want to be able to get up and get out of there in a hurry. But different strokes for different folks, right? We open the wine, start talking, look at the stars for a little while, and, when enough time has passed so I don't feel like a degenerate for making a move on her ... I make a move on her.

Boy, did I ever read those signs wrong. Ouchy.

Turns out, she was wearing jeans because it never even crossed her mind that she would be taking them off. "Did you think we were going to have sex? Outside?" (Yes. Yes, I did.*)

"I'm a grown woman. Why on earth would you try to have sex with me for the first time outside on a blanket that looks like it's been sitting in the back of your car for two years?" (It was one year and that's exactly where I got it.)

Then she said, "The least you could have done was to bring me back to your place and try it."

(*Obviously, she wasn't that well versed on Rule Number One.)

Rule Number Three: On top of that, when I made a date, I couldn't pick them up; I had to meet them there. I usually didn't tell people right away that I had kids and, even if I did, I never, ever muttered the word "minivan." The word "van" by itself is horrible. "Hey, wanna take a ride in my van?" Nope, never good. It sounds pretty rapey, actually. Now try adding the word "mini" in front of it. "Hey, wanna take a ride in my minivan?" I'm sure just reading it there are ovaries drying up all around the country.

So, I had no money to take people out, and I had nowhere to take them back to when I did take them out and, on top of that, they had to find their own way to and from whatever free places we were going to. I think it goes without saying that I got a lot of work done over that period of time.

I was completely frustrated because I was fighting my fate. There was no way around the fact that I had three kids. There was also no way around the fact that I was a horny dude who wanted to have boobies in my face. Then it happened. One day, a whole new world opened up. A world that was right in front of me the entire time. I was at the park one day when my youngest was about three years old. I had him on the swing and I looked over to see this row, I mean row, of good-looking Hispanic nannies.


One of the nannies, who had to be about twenty-four years old or so, was definitely checking me out, so I held Jacob on the swing a couple of times in a few poses that for sure showcased the guns.

Glanced over ... still looking. Game on.

I walk over to the row of women, started chatting them up, and as soon as they heard I was a single dad the whole tone changed. "Oh, what a great guy!" "Do you need help?" and blah, blah, blah. I could feel the difference with my little hot mamacita. I mean, as soon as she heard I was a single dad, it was like her temperature changed. Nannies? How come I had never thought of that before? We all talked a little longer until the ladies had to get the kids back to their houses for a nap. And that's when I heard, "Do you want to bring Jacob and have lunch with us at the house?" But it was said with a sexy Hispanic accent that is very hard to type.

Holy shit. I mean, this really applied all three of my rules: not my house, no money, and, honestly, who the fuck cares if I was driving a minivan because she was too! Nanny sex happened that very afternoon. Also that afternoon was when the "shift" started. Let's not think of who won't have sex with me because of those three rules; let's think of who will.

Who else might not want anyone in their messy-clothes-everywhere, sippy-cup- stained-diaper-smelling, too-tired-to-get-up-and-clean-a-fucking-thing apartment? Single moms.

Who might not have the extra money to go out to a $200 dinner because they have to pay for day care, diapers, dentists, and heavy medication just to stay sane? Single moms.

And who, out of anyone in the world, not only wouldn't run from but might run into a minivan? Single moms.

And then it really hit me. Wait a second, I have to completely change my eye level here. I don't have to hide the kids to pick up women ... I have to flaunt them. It was like bringing a puppy and a keg to the beach. I was instantly likeable and they attracted women. I know it sounds like I had decided to use my kids to pick up women, because that's exactly what I did. To be fair to myself, I never did it in a way that put them in danger or where they were being ignored or neglected. I did things like one day I was in the supermarket with my youngest son and we were in the fruit section doing a thing where he would pick up pieces of fruit and toss them in the air for me to catch in one of those little plastic bag thingies. It was our favorite thing to do in the supermarket and, apparently, it was also adorable, because when I looked up I saw a gorgeous woman smiling at us.

I said to my son, "Do you wanna play a different game?"


"Okay, you pick a name you want me to call you, any name at all, and that's what I have to call you for the rest of the day."

"Hmmm. Okay, I want you to call me Snake Guy! Snake Guy!"

Snake Guy? Worst name ever.

"My turn," I said.

"Okay, go."

"I want you to call me 'uncle.' Deal?"


And I walked over and talked to that cute girl. Questionable? Sure. Borderline wrong? Yup. Did desperate times call for desperate measures? You bet your sweet ass they did. He did great, by the way. He called me "uncle" the whole time. Brings a tear to my eye just thinking about it. Natural-born wingman, that kid.

I found out that there was a whole unexplored world out there that nobody was tapping into: Single Mommy Land. It was like Atlantis. You just had to know where to look to find it. Where could I go—that didn't cost me any money—to run into these elusive creatures? At first, it was like hunting Sasquatch because my eyes weren't trained to see them. In the past, I had ignored the flustered-looking woman who was wearing sweatpants in the supermarket and looking at a list, while shuffling through a pocket full of coupons. I would never look up to see the exhausted-looking women at the park, who sat in the shade with books, looking like they hadn't been off their feet since the beginning of time. I hadn't seen them because I hadn't wanted to.

Excerpted from It Takes Balls by Josh Wolf. Copyright © 2013 Josh Wolf. Excerpted by permission of Grand Central Publishing.
All rights reserved. No part of this excerpt may be reproduced or reprinted without permission in writing from the publisher.
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Table of Contents

1 Single Mothers 1

2 You Gotta Do Whatcha Gotta Do 29

3 Crushed and Flushed 54

4 Kids Are Pussies 76

5 Don't Be a Douchebag 96

6 Your Son Is Not Derek Jeter 128

7 Halloween 157

8 Stupidest Thing Ever 185

9 Teenage Boys Are No Bueno 209

10 Wrestling with the Future 238

Acknowledgments 255

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