Why Has Dating Become My Other Full Time Job?

That’s the question. And yet for many of us – myself included – it seems to be paying only minimum wage. So I decided it was time to give this some careful thought. How has something that by definition should be enjoyable – become a true labor of love? It shouldn’t, according to these first couple of definitions I found of the word “dating”. Take a look at how Dictionary.com and Oxford Dictionaries define the term “dating”:

“A social appointment or engagement arranged beforehand with another person, especially when a romantic relationship exists or may develop”

Go out with (someone in whom one is romantically or sexually interested)”

Sounds simple, fun and harmless enough, right? But then, here are these more colorful definitions according to the ever reliable Urban Dictionary:

“Of a couple, to be in the early stages of a relationship where they go out on dates to find out what each other is like, as a prelude to actually being a fully-fledged couple”

“James and Brenda were dating until James tried to fuck her on the third date.”

“A form of prostitution in which sex is paid for in installments rather than all at once”

Dating Karen is great. If I buy her two more dinners, she’ll let me touch her boob.”

And finally (and sadly) the one that may hit too close to home for many of us. And why dating may be seen by so many of us as that labor of love – with little or no pay off:

“A pointless waste of time… defined by massive usage of cologne and/or perfume, awkward sweaty hand-holding, and feelings of puppy love that usually dissolve in a few weeks (or less)”


Admittedly, I laughed at those last few. And there is definitely solace in knowing that whoever came up with those last few amusing definitions (that there is actually much truth to) has experienced those frustrating dating moments like the rest of us. But why does it have to be that hard? And frankly, that frustrating?

When I first got separated 10 years ago (yep, I am celebrating 10 years of “the re-invention of me” as I call it) – I thought dating would be a piece of cake. I was 35 when I decided it was time to start over. I was young, had a great job, could manage to hold a conversation, had good hygiene, no hunchback – and really no resemblance that one could speak of to Sloth from The Goonies. And I live in New York. How in a city of millions could I not find a (relatively) normal man to have a relationship with? The odds are WAY in my favor, right? Well, unfortunately they have not been. It’s been 10 years and here’s just a small sampling of some of my dating experiences:

  • The guy who interrupted my first bite of pasta so we could hold hands, bow heads and pray before breaking bread (my own silent prayer was “dear Lord, please save me….now”)
  • The guy who represented his height online as 5’8” – but when he finally got up from his seat at the END of our date, was maybe 5’3” at best (note to self – subtract at least 3 inches from height indicated online. And be leery of men who don’t get up from his seat to greet you at the START of your date).
  • The married guy(s) who obviously wanted to be single (and figured representing themselves as “separated” online was close enough). I guess when you write it in an online profile – or just think/wish something hard enough – it’s magically true (enough). Let the buyer beware. Enough said.
  • The guy whose jeans were so tight, there was no mistaking his endowment (but unfortunately, this was the same guy who was 5’3”)
  • The guy who had a phobia of going to brunch because he didn’t know if he would be able to order a “MIMOSO” – I suggested he could always go with the much more masculine BLOODY MARIE instead.
  • The turd who put his 5 year old daughter on the phone for me to chat with – before he and I had even met. I guess exploiting your children with a stranger is a way to prove to potential dates what a great parent you are. Asshat.
  • The narcissistic cop that (I believe) stole his accessories from Liberace’s estate (to each his own – but if your jewelry is bigger and more sparkly than mine, it’s a no go for me)
  • And lastly (for now) – the ex-con, recovering addict with Hepatitis C (for the record – I did not know this before accepting the date. He was hot and 12 years my junior, so there could have been potential here to earn my cougar stripes).


I’m guessing this lovely list gave some of you a chuckle. Maybe some of you are nodding in agreement, or can definitely top these (and if you can, please share below). But some of you – maybe some of the men reading this – are thinking I am a royal bitch that should die alone and I should give the guys a break. Understandable. Dating is hard for both men and women (although I would argue it’s a little harder and frustrating for women sometimes). It can really be hard work to first and foremost muster up the courage to put yourself out there – and then find potential people you’d want to go on a date with, meet the ones you weed out and spend a couple of hours trying to decide if there’s any connection here. Why would anyone want to keep doing this? But I will admit – as I think about these stories I re-counted above, amongst many others I have – at least these guys (as well as myself) were out there trying – and frankly opening ourselves up to being vulnerable with a stranger. And some of these things were not the deal breakers for me – but honestly, was just one more thing that helped me decide during that 2-3 hour first encounter that these people were really not good matches for me. But as with anything else in life – timing is everything. Things may come easy at times – but other times, you really have to work hard at something you truly want in order to get that result you’re looking for. So while there is no doubt dating is hard work – and frankly, we can make things harder for ourselves at times – here are some things I have learned and try to remember in order to keep at it:

  • Put yourself out there – sweetie, as much as you may wish it was the case – you are not going to meet anyone from your couch watching Lifetime (or Hallmark) – unless the cable finally goes out and your repairman is that very rare gem. Please visit the outside world. And run a brush through that hair before doing so.
  • Be confident – and learn to like yourself first. Why would anyone want to spend time with you if you can’t even stand your own company? Everyone has a bad day or moment – but if you’re eternally wearing a scowl and reeking of negativity, quit it. Pronto.
  • Take a chance – and don’t (always) wait for him. Some may argue that men should be the aggressor. OK, I would certainly agree at times. But if you see something/someone you want to go after, why always wait for him? Just do it. What is the big deal? Because we have our “rules” or need to always “play the game”? Well, rules were made to broken sometimes. And while I do love a good game of cat and mouse – games get tired of playing after a while. Life is too short for coulda/woulda/shouldas – and it may actually pay off.
  • Grow a thick skin – dating makes us all vulnerable and could make us feel bad sometimes. But try to remember that someone you really don’t know very well (or at all) cannot hurt your feelings – unless YOU let them.
  • Be kind – treat the people you meet with respect. Don’t be a dick. Just don’t.
  • Be open minded – there may be someone right under your nose with great potential that you just keep passing over. And guys – if you’re “friends” with a woman you’re secretly in love with, think about telling her and stop admiring her from afar or licking her wounds every time she shares one of her dating disaster stories with you. Sometimes we need our eyes opened for us, so just take the chance. Your only real excuse for not, is if you’re 13 and your balls haven’t fully dropped yet.
  • Repeat all of the above as needed – it can be tough, but (please) don’t give up.

So while I have clearly not hit the dating jackpot (yet) and it is pretty hard work to stay motivated at times – the point is that like any other “job”, it is what you make of it. Go in full throttle, you must put in the time, learn from experience, dust yourself off when you get a little banged up here and there and just have some fun. Eventually this labor of love will pay off. And if it doesn’t, you can always cash in on the stories from your book one day.

I’m clearly well on my way.