dating

When your kid’s friend’s mom is a MILF

Hey friends, it’s #TBT and time to check out a vintage column that originally ran in May, 2010.

Question to the Sexpert:

“ I am a single father of two boys. They live with me and their mother has no contact with them, but my parents are very helpful and supportive. I have been on dates since the separation and divorce, but haven’t made any connections. The mom of my oldest son’s best friend is a very attractive woman who is also single. We have become pretty good friends lately and I find myself becoming more and more attracted to her. I am hesitant to pursue this because if things don’t work out between us I don’t want to be the cause of my son losing his best friend. Thing is my boys were very withdrawn due to the neglect and abusive behavior of their mom (she is an addict as well as bipolar). My boys have come a long way from a year ago and I don’t want to ruin his friendship.”

I get letters that break my heart, I get some that cause involuntary eye-rolling and a few that are even funnier than this. But yours elicits something else: the strong urge to shake your hand.

The fact that you are so concerned about this and that you are so clearly looking out for your boys makes me think you are the perfect candidate for such a relationship. You’re approaching this maturely, thinking about the consequences and demonstrating that your duties as a father are taking precedence over your personal desires.  For those reasons, I’m giving you the rare, elusive and ever-so-shiny Sex with Timaree Official Seal of Approval.

Now, this is not going to be without awkwardness. But because your kids are friends, they’re likely to see any chance to hang out more often as a hugenormous bonus. They may take this news as even better than learning that a robot dinosaur is going to come stay at your house. As the adult, you can cultivate that positive feeling by presenting any relationship that might develop with this woman as: we’re good friends and you’re good friends, and we like each other and want to spend more time together. Isn’t that great?

But I’m definitely putting the cart before the horse. You and this lovely lady have become friends and she is single. She has just as much at stake, as a mom, but she’s also a woman and she should be approached as such. So before we can even worry about what would happen if you broke up, think about catching her interest, demonstrating yours and cultivating your mutual attraction. Also be prepared, as with any other potential date, to have the interest not be reciprocated. If that happens, make sure that doesn’t do anything to sour your relationship with her as parents of kids who are friends, too.

Many relationships can be dramatic, tempestuous and irresponsible because they have the freedom to do so. But dating between single parents requires being a little more upfront so nobody’s time gets wasted and a little more forward about what you want and need.  Less game playing, basically. Which really isn’t such a bad thing.

So go ahead, give it a try. Flirt with her, let her know you think she’s good looking, inquire about spending time more with her, maybe even time when the boys are not present if she’s game. Be upfront that you have thoroughly thought about the matter but find her so appealing that you couldn’t pass up the chance to tell her how you feel.  She’ll be glad to know you’ve considered the seriousness too.

Good luck to you and to her and to all of your kids. You’re all very lucky to have each other.

Questions? Comments? Violent reactions? Email sexwithtimaree@gmail.com or tweet @timaree_leigh See more at http://www.facebook.com/sexwithtimaree and http://tinyurl.com/swtpod

Leave a Reply

Fill in your details below or click an icon to log in:

WordPress.com Logo

You are commenting using your WordPress.com account. Log Out / Change )

Twitter picture

You are commenting using your Twitter account. Log Out / Change )

Facebook photo

You are commenting using your Facebook account. Log Out / Change )

Google+ photo

You are commenting using your Google+ account. Log Out / Change )

Connecting to %s