The Bad Women of 30’s Dating

This post isn’t scientific but from my real world experience of dating over the past few years.  The old cliche is that the dating pool in your 30’s is pretty bleak and I can say that’s very true.  Lets focus on some (not all) of the women you’ll encounter when dating in your 30’s.

The Clueless Serial Dater

She’s on a few different dating sites / apps which makes you think she’s tired of being single and is ready to settle down, except she isn’t.  I’ve dated many of these over the years and they’re all still single to this day.  Why?  I really have no idea, but generally you can assume its because she either has no idea what she wants, is still hung up on a long moved-on ex, has serious commitment issues or is simply content going on a couple dates per week to have a free glass of wine bought for her and nothing else.   She’s been doing this so long that no guy really has a chance (she goes on 50-100 dates a year) you’re just a number to her and her mind is elsewhere.  Where?  Who knows and who cares.  Avoid.

The One With Mental Health Or Other Problematic Issues

This one is hard to explain, its kinda like that guy who was asked to define porn in court,  he said he couldn’t define it but knew it when he saw it.  You’ll know this one when you run into her as the disorders are of such a wide range.  They range from general man hating to severe unchecked depression and everything in-between.  The first few dates will go seemingly well, but their true self comes out eventually and most men run for the hills.  This prompts her to periodically delete all dating apps, but she’ll be back – as always.

The Ones That Expect You To Also Date Their Families

Rare, but still out there even during 30’s dating.  This one is perfect on paper and you’ll be awestruck as to why she’s even single in the first place.  It’s because she’s in search of some messiah that doesn’t only meet her standards, but also her fathers, mothers, brothers, sisters, aunts, uncles – you get the idea.  This is the one that already has the 500 guest wedding pre-planned, she’s just looking for the right groom.  I am not against this, but we’re in our 30’s here – that ship kinda sailed over a decade ago and with a certain clock ticking, I’d think something else is more important at this stage than a $100,000 fantasy wedding.

The Ones That Lie

The mechanical engineer that was actually an environmental student, the IT professional that was actually a clothing retail employee, the IT professional that was actually just the receptionist for the place, the teacher that was actually a server at a pizza joint,  the countless time wasting re-bounders that bail the second they realize they aren’t ready to date after you have fully invested yourself, the ones using pictures of themselves when they were in college and 80lbs lighter and the ones that say they have one kid but actually have three








My Very First Online Date (2002)


I was 22, wasting youth like you don’t even know, working night shift at a factory.  I bought my first cell phone, a brick-like thing, almost as heavy as one.

I ran three machines, from 11pm – 7am.  It was a huge factory, but there were only 10 of us on the night “crew”.   I literally pushed buttons to start each machine, in a circle, then wait for 5 minutes until they finished and needed to be re-filled – all night, every night.

Gun drills they were, these little tubes of knurled-end steel would eventually end up as column shifters in Ford and Chevy pick-ups.

A mindless, boring gig – that you do before you know where your life is heading.

This was when I pulled this “brick” phone out of my pocket and started exploring.  It had an “internet games” button.  Once in there, besides the stupid games there was a “chat” option – so in I went.  It was actually pretty cool – it was like Twitter, but you could make your own group or discussion topic and others would pile in.

Remember, this was a phone without a qwerty – to type out a message you had to use the numbers – press #2 twice for B, #9  once for W, #7 four times for S.  Sounds hard, but it became second nature and I could bang out sentences almost as fast as I can today…

Wasn’t long before I was part of a semi-local clique, and for some reason this chat group attracted Toronto strippers like magnets.  I guess they too would dive into their phones after a dance, when claps were sparse and the room was empty – but it became an addiction for them.  I’d do overtime shifts, Saturday nights and they’d be on there even more.


There was an outspoken member Superm0del 

Very funny, up to chat about anything and frankly, just super cool.  At first I thought this was some whale – or worse – an old man, using the name to generate attention – no pictures here folks, you mailed them to your suitor.

Turns out she had recently quit peeling on the Toronto circuit and was back living at home trying to get her shit together.  Another member of the group barked at me “she looks like Cameron Diaz, she isn’t a pig”

She actually looked better than Diaz…

And I still have the Polaroid she sent me – I just spent 10 minutes looking and can’t find it, think big titted blonde surrounded by juice heads in a bar, and you’re close.  I’ll post it on Twitter when I find it.

Our convos started as banter  but we eventually fell for each other, one day my first name preceded Superm0del in her screen name.  That meant lust back then.

Meanwhile, we were committing the biggest sin ever – falling in love over text before meeting.

Eventually we arranged a meet, somehow I got her to drive an hour to me and we met beside a phone booth at a gas station, to where she was lost and I drove to find her.  She was hot, but a bimbo for sure – big boobs, big hair, make up, tight jeans, heels….

I loved what I saw, she didn’t reciprocate – I was a thin, malnourished, poorly dressed, pale, inexperienced, been hanging out from 11pm-7am in a factory for the past year “thinking she’s gonna love me off just what I do online” kid.

I was 22, she 26.

I didn’t know this until I went for the kiss at the end of our date, which consisted of beers and pool at an Applebees.   I got the cheek.

I sent her a message right away letting her know my increased lust for her…

I got shot down with “I dunno, I like you, but I usually date bigger guys, and this hurts like hell”

I did the best thing ever, and I said ok and backed off, admitting defeat – which hurt, but I knew it hurt her just as much.

It wasn’t 3-4 days and she wanted to meet up again – this time  a movie at my place (a farm house in the middle of nowhere southern farm county Ontario)

She again got lost on the main drag, so I went to get her, we got a movie from a place called Blockbuster you have probably never heard of 😉

We watched the movie in my bed – now, strippers aren’t your “usual bears” they have been hit on and had offers by everyone, incl pro athletes and actors – so there isn’t any game for me to play here, and being younger than her – no hope in hell.

She barked at me afterwards for having a 26’er of whiskey on my dresser “WAS THAT TO GET ME DRUNK SO YOU COULD FUCK ME???”

During the night we never hit it, she did end up taking home with her few kittens we had acquired from one of the barn cats – which she later dumped at an animal shelter, while not being allowed to, and getting yelled at by the guy, and calling my in the midst asking how to handle it “TEAR THE FUCK OUTTA THERE” I recommended – she did.

After that I was invited for date 3 in her bedroom.

She lived with her parents – she had me come in the garage door, then hustled me up the stairs.  “lay down” and she left the room.  She came back in just a t-shirt, barely covering 30% of her ass – which was beautiful….

We had an awesome night – in the morning she told me to keep sleeping and left to go get us breakfast, she came back with breakfast bagels and coffee – OMG, this was heaven.

Part 2 Next…