Every now and then, I think about what if I was to find myself single again. I’m approaching 40 (it’s the new 20!), I have two boys (complete darlings!), and I would be facing the possibility of dating all over again (I bring teh hotness!1!). I just celebrated my 7 year anniversary and I was a contented single person. However, the thought of dating period, much less navigating those treacherous waters with kids in tow, reminds me to pray that my wife will outlive me.

To a degree, I can still sympathize with trying to date while having kids. It’s hard enough finding the time to go out with just your spouse, to keep the relationship fresh. One of the reasons we decided to stop at two kids was that we could still find people to babysit for two (free!). Around three or more, we weren’t just paying, but we would be paying big. Or else making better friends. Many folks find themselves single with kids or single again with kids or have to go through the motions of weighing the pros and cons of dating someone with kids. There are many issues that they have to check off. Issues like:

-going from being single to an instant family
-dating while juggling kids
-dating while dealing with ex-spouses or the children’s other parent still having to be around
-blending two families
-how and when to develop/allow the appropriate attachments

It’s a lot to absorb and deal with on top of trying to figure out if you like the person you’re going out with, though every relationship has its baggage. I talked to a few friends of mine to see how they handled dating folks while having kids, and a few similar threads kept coming up.

1) Take time before introducing the kids to the other. Okay, one person I talked to made it a point to not introduce her kids to whoever she was dating until the relationship had lasted a year first. Your timing may vary. The point is that your first responsibility is to your kids and creating a stable environment for them. You don’t want to confuse the kids with a constant stream of “friends.” And the simple fact is that it’s important to see if the two of you are going to work as a couple, if they are worth the time/emotional investment, to move to the next level.

2) Take the attachments slowly. Judge the children’s reaction to your significant other and your significant other’s reaction to them. For one thing, you don’t want to let the kids get attached only to have your “friend” disappear. Break ups are hard enough on adults, but they are even tougher on kids. On the other hand, you also want to allow time to allow the relationship between your children and your significant other to develop naturally.

3) Be honest and upfront. My sister handled introductions this way: “Hi. My name is Ro. I have two kids.” It puts the facts immediately out there and gives them an out that way they can run if they’re going to run.

4) Realize that where there are kids, there are parents. A baby momma/daddy may still be in the picture, another party to your relationship. Like any other family, you inherit them as a part of the relationship. If there is any drama with the children’s other parent, that needs to come up pretty early in the discussion also. (I’m thinking that “By the way, the baby daddy’s crazy” is a date three conversation.)

The key rule to relationships of all sorts boils down to how best you can love one another, your kids and yourself as you seek to find your own happiness. This topic is way too big for me to gloss over in one blog, no matter how lengthy, so I may me re-visiting it again in the future. What are your thoughts?

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