Sleepless in Chicago: Is Dating a Single Father a Do or a Don't?

06/02/2010 03:07 pm ET | Updated May 25, 2011

According to the U.S. Census Bureau, there are 13.7 million single parents in the U.S., of which, 4.4 million are single fathers. As a single girl who dates more than she cares to admit, I am surprised that I have never gone on a date with a man who has a child. I have never really given this topic much thought until this weekend, when I found myself checking out a handsome man, with two beautiful little girls, while laying out at my friend Jodie's rooftop pool.

Super Dad was so patient, kind, and attentive to his two little girls, and you could tell by the sparkle in their eyes that they adored him just as much as he adored them. When I heard him call the girls over for lunch and unpack a picnic basket, even my heart of ice melted a little bit at the sight. I turned to Jodie and asked if she had seen him around her building before and was wondering if there was a Mrs. in the picture? She shot me a look that said, I know what you're getting at and I'm not sure it's a good idea, but then mentioned that she hadn't ever seen him with a woman--just the kids.

On my way home that afternoon, I ran into Super Dad in the elevator and struck up conversation about how I saw them at the pool earlier that afternoon, and how he seemed like a wonderful father to those little girls. He thanked me and told me that they are his world and after a few months of raising them alone, he was finally settling into being a single dad. I wasn't sure if that was just friendly elevator conversation or a green light for me to flirt, so me being me, I decided I would choose the later and tell him that if he ever needed to escape for a while, he should give me a call and we could grab coffee or an adult beverage. He took my number and told me that he's always up for company, especially with someone over the age of six.

He called me Monday and asked if I had plans later that night. He apologized for the short notice, but wasn't sure if the girls' mother was going to pull through on her end of the deal and take them for the night. He said that he could use a stiff drink, so we met at a bar downtown by his place where the bartender was heavy handed with his pours.

Super Dad and I hit it off immediately. He had a smile that was warm and inviting. He was charming and confident, yet sweetly modest, which made him incredibly endearing. We were on our second round of drinks when his phone rang, and he excused himself to take the call. He was gone for a few moments before coming back to the table with a furrowed brow and cash in his hand. He apologized for having to cut things short, but his ex wife decided half way through her time with the kids that she would rather go out with her friends than take care of the girls, so he had to run off and pick them up. He asked if he could see me again and make up for the abrupt exit. I told him of course and to give me a call, but in the back of my mind I couldn't help but wonder what I was getting myself into.

On my cab ride home, I couldn't seem to block out the flurry of questions that instantly flooded my mind: Would we have any time to see each other alone? Will there be any baby mama drama? If things get serious, am I ready to have this child in my life forever -- because sometimes I can barely take care of myself! Lastly, one day I want to have kids of my own and start a family, and I think there is something special about experiencing that "first" together (because lets face it, I can't really say that all too often) and I won't be able to have that with Super Dad since he already has children of his own.

In a city where women outnumber men 2 to 1, should I let something like this become a deal breaker? Or should I face the fact that as I get older, the chances of experiencing those "firsts" with someone (i.e. dating a man who has never been married or doesn't have children) are going to decrease? The more I think about it, I'm not sure if that's such a bad thing. When seeing the way his face lit up while he talked about his daughters, and to hear all of the sacrifices that he has had to make for them, at the very least, I know that he is a man of great character. One who doesn't run from responsibility or tough situations, and as a result, is a man of maturity and substance. That's not too shabby, and lets face it folks, that's more than I can say for most of the men that I seem to date.