Welcome to I suck at dating.  I’ve done a lot of dating over the last six years, most of it pretty awful.  Maybe you’ll find it amusing, maybe you’ll find it offensive, maybe you’ll think I’m completely insane.  I don’t think I would disagree with you.  There was definitely something cathartic about writing all this though.  I feel better having it off my chest, whether anyone else gets something out of it or not.

So, where to start? I’ve had a string of bad dates.  Maybe not so much a string, maybe more like one of those monster ropes they use to tie ships to shore.  I probably described that incorrectly, but you get the idea.

I guess I should start with some background.  I’m a single white female in my mid 40s.  I’m also a single mom of a 24 year old son.  His father took a walk.  Unfortunately not off a pier, just far enough away from us to knock up someone else.  Sometime very shortly after my son was born during my sophomore year of college, I decided that I needed to be independent.  I needed to always be able to support my son and myself without help from anyone else.  I’m talking financial support.  My dysfunctional family provided as much emotional support as they were able.  And no, I am not saying I’m the normal one in the family.  There is no normal in my family.

So I spent the next 18 years focusing on my son and my career.  I rarely dated, spent all my free time at baseball, soccer, and boy scouts, and my career was fairly successful.  Around March of my son’s senior year of high school, I realized that he would be going off to college in a few months and my life would suddenly be very very empty.  I did what anyone would do in that situation.  I panicked.  A friend once told me that her mom had the same realization when her youngest sibling went off to college.  She said her mom found religion as a hobby to fill the time.  I found dating.

I am sure I went about it all wrong.  Don’t forget – while everyone else was “sowing their wild oats” in their early 20s, I was raising a toddler.  I’m not saying I was socially stunted when it came to dating, but I probably was.  3.5 years with your high school boyfriend who splits when you get knocked up does not make one confident about men. He also managed to beat me up a couple times, once while I was pregnant – he got that in as we were fighting about me refusing an abortion (I am not anti-abortion, I think every woman deserves the right to make that choice for herself.  I just couldn’t do it and feel like it was something I wouldn’t regret), and the second time in front of our five year old son.  I really know how to pick them.

What follows are stories of the dates and guys I met during the next six years, late 30s into mid 40s for me.  I definitely made up for a lot of that lost time from my 20s.  Let’s not get into slut shaming here.  I fully agree that I should have been more selective and careful about which guys I dated and with whom I had sex, but be honest, if I was a guy, I’d be a hero.  I absolutely did not sleep with all of the guys who will be detailed in this confession of my crazy escapades.  Give me a little credit, please.  And please don’t judge me too harshly; I already do that quite well on my own.

I met almost all of these guys online.  It turns out that having a successful career, working and raising a kid, didn’t leave much time for socializing.  I had about zero chance of meeting a guy in my daily life. I used many dating sites.  It didn’t matter what site, odds were a guy was on more than one, and you would meet a guy on one site, and your friend would find him on another.  I know because I, my single sister, and two single friends all ended up checking with each other before getting involved with a guy.  For example, a guy I met on one site tried to date my sister on another.  This happened with all of the sites.  There seems to be a limited pool of guys in our age range and they’re all using the same sites.  I met some guys through two sites on my own as well.

I’ve changed most of the names to protect the innocent (and not so innocent).  If I got something wrong when recalling what a specific guy said to me, I apologize.  I am in my 40s and my memory isn’t what it used to be.  I will also note if a guy was significantly younger than me, as I dated many younger guys, but very few older ones.  That cougar thing is real, believe me.

If there aren’t a lot of details on a guy/date, things were relatively OK.  He just wasn’t the one who made me feel something, I’m not sure exactly what.

I just want to say upfront, I don’t think I am anything great.  I think most people think I am at least somewhat attractive, and I know I am intelligent.  I think I’m funny, but most of these guys didn’t.  I am a huge smartass.  I am not saying I am better than any of them, just that I had some weird experiences trying to find one I could stay with long enough to learn his last name.