Online Dating at Forty: The Struggle Is Real Pt. 1

I remember being in high school and thinking that by the time I was twenty-five I would be married with two children, a house and a fantastic job that I loved.  It would look something like the Huxtables but with less kids.  Twenty-five seemed so old to me back then. I mean you could spot the guys twenty-five and older when you were out because they looked so…old.  Not older in the sense that he was an attractive man for his age but more like the way you view a dad or uncle.  They seemed so grown up and settled in life and that was far away from where I was. So pretty much I was like John Snow…I knew nothing.

In the blink of an eye I went from eighteen to forty and my life looks nothing like I thought it would when I was a teenager.  Hell, it doesn’t look anything like I thought it would when I was twenty-five, thirty or thirty-five.  I wouldn’t say I was delusional but more so an optimistic hopeless romantic. Well at least I was until I hit forty.  They say life gets better at forty and I can say that you do become more self-aware and confident in who you are.  Unfortunately, that doesn’t really help when you are forty, single and dating.  Oh yeah let’s not forget childless.

So, as you are aware, I moved across the country to a city that was practically the total opposite of what I was accustomed to.  I mean I literally went from Chocolate City to the Whitest City in America.  As a chocolate girl I knew beforehand that I would have to open my dating options a little.  By this I mean dating outside of my race.  That isn’t a scary concept to me as my mother was known for dating a white guy here and there while I was growing up.  My big dilemma was how open would the men in my new city be to date a black woman.  At least I thought that was going to be my biggest dilemma.  It turns out the largest obstacle in this adventures was navigating the online dating landscape.

As a woman that is not photogenic, fat and rocks a resting bitch face, the profile picture is the dream killer. After taking way more selfies than a Kardashian just to obtain one halfway decent photo that looks anything like you do in the mirror on a good day, your self-esteem is now shot to hell and you start to contemplate the pros and cons of being single for the rest of your life because let’s face it, you don't have it in you to take one more picture that hides the bags under your eyes and doesn't make you look as miserable as you feel.

Like the grown forty year old woman that I am, I pull up my big girl panties and select a few pictures that realistically all look the same.  The next step is to start working on my dating profile that will dazzle my prospective suitors.  I equate the agony of writing a dating profile to that of a work resume.  Writing about myself isn’t easy for me hence the sparse blog posts.  Anyway, I come up with something that is honest and a bit witty just to have majority of connections I made ask me questions that I addressed in my profile.  Point being, its all about those damn pictures.

Well, my first date was with a guy we will call Brian. We chatted back and forth online for a couple of days before we exchanged phone numbers.  He had a job, a car and his own place (at this age your requirements become a lot more basic.)  On top of everything he made me laugh.  We agreed to meet at a Thai restaurant for dinner.  I pulled up and my first red flag was he lied about his height.  I’m what you would call a short girl and like most short girls I like a tall guy.  He claimed to be 5’10 but he was more like 5’6.  Not a complete deal breaker but it was noted.  The next flag was that he came to a first date dressed like a bit more casual than I expected.  This was something that I had to adjust to be because my new city is very laid back and outdoorsy.  Again, not a deal breaker as much as it was more a note to self for future dates.

We were seated and the conversation flowed very nicely. He was funny, attentive and easy to talk to.  Towards the end of dinner, I asked him one of my qualifying questions…if he had ever been with a man.  His response was he is sexually fluid.  Say what now?  Yes, that was my response.  Well, this was a few years ago and I was not familiar with that term.  He nicely broke it down for me that he is attracted to who a person is and not their sexual orientation. He also clarified that he had never been in a relationship with a man and he is sexual partner breakdown was 30% male and 70% female. Needless to say, we chatted a few times after that but never saw each other again. He was a nice guy but I don't think we were a match made in online dating heaven. 

So after my first online date, I realized the dating lanscape is way more complex than I anticipated.  Not that I thought it would be easy but it really is a mind fuck.  It's not for the faint of heart and it has taken me through some serious emotional highs and lows.  I've see potential in some that has fed me lies and I broke some hearts in my quest for love.  This is where I am in my life and I have no clue if I will find love in the end.  I just hope in the end of this journey I have some great stories to tell.