Single Parenting & Dating, Are You Ready To Roll The Dice?

ID-1009919Ahhhhhhh, dating, the bane of most single parent’s existence.  On one hand, we would love to have a partner to talk to, eat a meal with and see a movie above a G rating. On the other hand, given the precarious nature of dating, nobody wants to introduce their kids to someone, and then have that person magically evaporate soon after. Parenting is a tough gig.  Single parenting is even tougher. But Dating and Single Parenting can be a shit storm of epic proportions if not handled well.  The planning needed to coordinate a sitter, co-parenting schedules, dates with said “date” can be enough to make most single parents say forget it!

Recently single…again…after 8 years…I am faced with the “idea” of dating.  I have to be honest…I dread it.  I divorced in 2005 and then met a man later that same year.  We had a son together and worked our way through 8 years of interesting challenges.  In 2012, those challenges proved more than we could work through and we ended our relationship.  I am now in the mindset of  “if I never ever date again, that’s totally fine with me!”  Not because I think all men are bastards, but because I am deeply focused on creating a safe space for my kids.  They, up until this point really had very little say in how life moved along.  Now that two of mine are older, their opinion and feelings weigh very heavily on my decision making process.   My youngest is 6 years old and he is dealing with his dad not being here full time anymore in his own way.  He has become more of a snuggler, which I don’t mind at all!  My daughter’s say they just want me to be happy and whatever I decide is okay with them. The question is , what am I okay with?

Dating Dilemmas

New Underwear!

Shit!  I need new underwear if at some point in the next year someone is going to see me in anything less than a date night outfit!  Not that the stuff I own isn’t nice.  I’m a big believer in wearing sexy lingerie all the time, however, my current sexy wear carries the ghost of my past relationship.  If he hated it, won’t the new guy hate it too?  If he loved it, will it taint my feelings about showing it to someone else?  Will that damn ghost of relationships past fuck up my chances of getting laid again? Have you ever had ghost memories mess up your current state?  THOSE GHOSTS EXIST IN UNDERWEAR TOO!!!

Guerrilla grooming again!

Okay, don’t misunderstand me here.  I shave, wax, pluck, primp and pamper, but in a long term relationship there are times when you let it go for a while. Am I right ladies? After all, you KNOW you won’t be having the sexy time for a week (wink wink nudge nudge) or so, does it really matter if I shave my legs TODAY???  Now, in the dating world…the sex ninja could attack at any given moment and I need to be ready!  God, the last thing I need is to look like a 70’s porn star with a bush the size of the White House Rose Garden!  I will need to add my waxer to speed dial again.  Damn.

Foot Fetish!

Okay, I’m a socks and shoes girl, or slipper girl in the house.  I pretty much have those piggies covered up most days.  I quite love my light up Christmas tree slippers that I bought for myself and they can, in one fail swoop, knock the boom chicka wow wow out of any man’s stuffing.  So, now those slippers will be tucked under the bed and only be worn when I know for sure said date is way, way out of town. I don’t do ambush well, and being ambushed with sex killing slippers on is definitely NOT on my list. Add to that, now I need to make sure my feet are in a constant state of pedicure.  The very LAST thing on my list is tossing dry scratchy feet over a man’s shoulders and leaving road rash on his back…(I take Yoga ok!! Shut up!)  Have you ever had someone run their dry, sand paper feet over your legs? NOT FUN!

The expense of dating again…HIGH.  Return on investment…statistically low.  What’s a woman to do?

New underwear:  $100

Bikini Wax, Leg Wax:  $125

Pedicure:  $60

$285  for the chance at love?  Hmmmmm … I can get a dozen cupcakes and rent a chick flick for under $50, perhaps I’ll go bat for that team for now.

What about you Toy With Mes? Have you jumped right back into the dating pool or do you dread it? What’s your biggest fear/concern about starting all over again?

Free Digital Photos. Photo by Michelle Meiklejohn.



  1. I just don’t date period. For no reason other than it’s a pain in the ass. Men want to go out after work and that will not work with my schedule. Who wants to go out after you’ve already been out at work all day and you have a house full (of behaviorally challenged dogs) to take care of? Let’s not forget about housework, personal email, laundry, cooking and then getting up at 5am the next morning to do it all over again?

    No, dating is an inconvenience that I don’t have time for. Perhaps one day I’ll meet someone worth being inconvenienced for but out here on the mountain the pickings are slim so I’m not holding out hope.

    • Natalie

      Jess, so so so true! I can’t just drop everything and go for dinner or away for the weekend. Add to that…MY KIDS COME FIRST! The biggest turn off is a man that gets pissy over me saying no to him to do something with my kids.
      It is inconvenient, and quite frankly….I like my life the way it is right now.

      • Toy With Me

        I’m hearing from more women all the time that are separated or divorced and have children who would rather just focus on themselves and their kids as opposed to looking for another relationship. Is this a new trend, or something I’m only noticing now that I’m in this situation?

  2. Toy With Me

    After being married to my high school sweetheart for 25 years and now separated for almost two, I have yet to date. Seriously. Not one single date. Why? I’m afraid. Afraid of rejection, of trusting, of being accepted, of my own judgement. I’m scared shitless that maybe that was my one shot at love and now it’s gone. I don’t even know how or where to begin. Online dating freaks me the fuck out, so yeah, not trying that one. Plus I work, a lot. So time is also an issue. And if I’m being honest with myself I just don’t think I’m ready. Some scars take a long time to heal. I’m still dealing with that.

    • Natalie

      I hear ya!! I don’t want to have years of discussion about gold fish crackers alone, but in the same breath, I don’t want to set myself up for hurt or even dating failure. I suck at many things and if I don’t date, I clearly WON’T suck at dating.

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