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Does the enemy wear Underoos?
  • November 11, 2012 : 16:11
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As people grow older, their list of must-haves in a potential mate grows exponentially shorter. So when I decided to get back into a serious relationship, I had three things I required in a man. Two of them were huge testicles. The other? That those testicles had produced absolutely nothing except shock and awe from those who had seen them. That’s right—I wanted a guy with no kids, and it was something I would not compromise on. I was determined to be the only whiny, spoiled brat in my next relationship.

Every new partner you hook up with brings along some baggage. It could be self-doubt, jealousy, clinginess, fear of commitment—but sometimes it’s the type of baggage that has freckles, SpongeBob Underoos and a trunk full of toys. No, not Carrot Top—a child.

As the producers of 16 and Pregnant can attest, there are more single moms out there than ever before. Whether through divorce, choice or a drunken Kappa Delta mixer, a surprising number of single women are dragging tousle-haired, nose-picking germ machines behind them.

Some guys avoid chicks with kids the way Mel Gibson avoids Hanukkah. This is a mistake, fellas. Dating is tough enough. Why reject an otherwise good prospect just because she squeezed out an ankle-biter a few years back?

But dating a woman who already has a kid or two—or 14, in the case of the Octomom—can be a challenge. There’s no bonding, no unconditional love. You’re basically dating a MILF with a gonad goalie intent on keeping your puck out of Mommy’s net. However, there are some definite pros to dating a woman with kids. So how do you know if you’re ready to be someone’s not-real daddy?

Since I am nothing if not a cynical Sally, let’s start with the cons. Whenever you go out with Ms. Mom, she’ll have to get a babysitter. Either that or you stay in, which means the only doggy-style you’ll get is watching Beethoven 7 with her and her little human chastity belt.

If you go the babysitter route, it can still suck. You both spend the whole night looking at your watches—she to make sure she’s not going to be late and you to see how much time you have left to try to bang her somewhere between the restaurant and her front door. More often than not, you drop $200 on dinner, get a peck on the cheek, and by 10 o’clock on a Saturday night your big date is over. She goes home well fed, and you end up jerking off next to Fred Willard in a porno theater.

God forbid things get serious and you want to take a vacation together—guess who’s tagging along. Forget that week of debauchery at Hedonism in Jamaica with unlimited booze, food and sex on the beach. Instead, it’s a week of Disney World with unlimited complaining, crying and pants crapping. Instead of sailing across the crystal-clear blue waters of the Caribbean in a catamaran, you’re spinning around in a freaking teacup. And believe me, with the kid around, the only thing you’re banging on the beach is your head on one of the volleyball posts for agreeing to this celibate sabbatical in the first place.

So should you take the first bus out of Toddlertown? Not so fast, Captain Kid-Hater. There are as many pluses to dating a baby mama as there are minuses.

Dating a chick with a kid is perfect if you’re in the relationship purely for the sex, because that’s all she’ll have time for. Juggling motherhood and a career doesn’t leave a woman enough time to make you sit through a Real Housewives marathon. Being with a Mom-o-matic practically guarantees sex. There’s no way she can play the “saving myself for marriage” card when there’s living proof of her sexual activity sitting next to her, loudly humming the Barney theme song while eating his own boogers.

Dating an unmarried mommy is also a good way to keep your independence. If you mention to a nonmom that you’re thinking of jetting to Vegas for the weekend, she’ll pack a bag quicker than Woody Harrelson packs a hash pipe. Suddenly, your weekend of strip clubs and gambling has become a romantic getaway full of Cirque du Soleil and couples massages. A mom, however, will have her kids to take care of, leaving you free to spend the next two days in a Hangover-like frenzy.

So don’t sweat it. If a kid is part of her package, just roll with it. They’re cute, they’re amusing and they’ve already got a dad they can take their resentment out on. Don’t look at a kid as a mood killer. Look at him as a little noisy butler who will go get you a beer out of Mommy’s fridge for a quarter.

True, I decided that mo’ kids equals mo’ problems. But you might want to give a woman with a kid a shot. By all accounts, having a child is one of the most special miracles in the world. Besides chocolate. And weight-loss surgery. And Lindsay Lohan finally being sober. And with a kid, remember, you’ll always have someone to play Xbox with when it’s Mommy’s time of the month.

read more: Sex and Dating, Funny, ask playboy, dating advice, issue november 2012


  • Anonymous
    First of all I can tell Lisa has no experience in what she is talking about, nor has done her own homework on the piece she has written! I have been happily together with a single mother for four in half years! Though it is hard to be a father figure but not actually having the title of dad, I had to earn the respect of the kids. And they respond to me even when punishment has to be given, for neglect in school work or neglect in respecting their mothers wishes and even consider me there parent when brought up in conversation! To discuss the issue of my sex life with a single mother! Well , all I have to say is we fuck, make love, and have our porn nights without video! The best blow jobs without asking, or begging! Lisa you have no idea what you are even talking about! This being said it has nothing to do about sex, it has to deal with you offending my girlfriend, and her being a single mother. Saying “that is all she has time for” is the stupidest comment a woman could ever make, because most the time she does not have time for it. There is a lot more that goes into dating a woman with children and it does not include having “Hangover” type weekends alone without her or having great sex because “that is all she has time for”. If you are dating a woman with children you need to be prepared for what comes along with that, for example, being a parent when the other half is not involved, and taking on the roles needed for those children. If your mindset is only about the sex and the partying weekends without your woman than a single mother should be last person on your list to date, and she should have pointed that out, not making those aspects a plus side. This article should have offended every single mom out there and should have never been posted in a high quality magazine such as playboy. It actually makes me rethink even getting the magazine if they are going to post garbage such as this article was. Brent, Manchester, MI
  • Anonymous
    Dating a woman with kids isn't usually the issue, it's the idiot ex that donated his 50% genetic material that is usually the pain in the ass.
  • Anonymous
    I read this piece in Playboy Magazine, very well done, funny as usual, thanks Lisa.