The Challenges of Dating as a Single Parent

Melissa Mensavage

my last boyfriend, three months prior to my first pregnancy.

I think I’ve talked about this before.  Its always on my mind.


I don’t even know where to start with it.  Even sitting down to write this I have many long pauses between sentences and thoughts.

I should probably start with I never was a big dater, even in high school.  I remember clearly my first high school crush was on this boy Mike.  Mike was tall, thin, curly mullet hair with a big smile and big brown eyes.  But he never wanted to get to know me.  Probably because we ran with different crowds, moreso I was still trying to find my place in that world seeing I had just moved to the area.

The boys I did date I always felt like I had to date them because they were interested in me, not because I was interested in them.  I also felt ashamed to be dating them because they didn’t meet the match of the ‘popular’ people – the crowd at the time I desperately wanted to be a part of.

My insecurities kept me back from many things, let alone a good solid boyfriend.  Even to this day, they are still around holding me back from meeting the nice guy.  My frustration with them is exhausting.  The questions are never-ending and play over and over in my mind, I cant believe I am actually going to say these out loud – how do I know I am doing ‘it’ right? Or is this what I am supposed to be doing – holding hands in public, saying this or that?

These foolish insecurities that I’ve been carrying with me since my teens, that probably attributed to the demise of my marriage when I was in my twenties, are getting to a point where they either grow up or move out.  I can feel them surfacing now, when I am starting to entertain the idea of dating.

How can I expect to even meet someone when these stupid things are hanging around?  Why at this age should I even care what other people think?

I go back and forth with these all the time.  I also worry about dating takes time and that is time away from my kids.  My kids are young right now and they are changing every single day, and I waited far too long to become a mother – especially in an unconventional way – that I am not sure I want to miss these days.  So unless I know right away the guy is a possibility there is no point in my dating.

But then I get real lonely at family functions or especially as of late a work banquet where everyone was there with their spouse or significant other (literally I was the only person without a ‘plus one’).  Talk about awkward and it is then I know for sure I want to be with someone.

So how do I do this?  On the recommendation from a friend, I joined a dating site.  I’ve viewed profiles, found a few interesting, took time to write a few and I’ve heard nothing.  Don’t get me wrong, I’ve received interest from what seems like the clan of Duck Dynasty, I’ve learned that what they say about black men is true (clear pictures and all were included), and know that men are definitely interested in women younger than them, like 20 years younger.   It is with this I close my computer with disgust and defeat and crawl into bed and want to cry my eyes out.  Though as quickly as I find myself in this funk I am just that quicker brought back to reality with the cries from the boys bedroom.  As I pick up my teething infant I figure dating can wait just a little bit longer.

**picture is of Stefan, my last boyfriend.  This was three months prior to my pregnancy with my eldest son. 

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