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








3 Date Week (system revamp)

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Blog #19

This past week was very busy for dates, I had them on Tuesday, Friday and Saturday.

Tuesdays date was one of those office girls that loved her job and essentially lived at her office.  We had been tossing random messages back and forth for around 3 weeks before I initiated a meeting and she quickly agreed.  We met at a coffee shop on Tuesday evening and it actually went ok.

This was a girl that could’ve probably worked out but since I was so busy I never got back in touch with her after our date.  Although, when leaving the coffee shop and heading to our cars I went in for a hug and it felt very awkward – after that I had a feeling that while she likely enjoyed my company and conversation, it was unlikely any request for a second date would’ve been granted by her.

After all this dating, I’ve began to just trust my gut instinct as its usually bang on with this type of stuff.

Fridays date was pretty bad actually, in its own post it would’ve been called Teacher #4 but there just wasn’t enough substance to warrant enough words to make a singular post about it.  She had initially engaged contact first, we sent messages back and forth and then I asked to meet in her area.  The problem with that was there weren’t any good cafes or coffee shops in her area, so we ended up at a dessert bar type-place.

So picture this, her a little over dressed, me a little under dressed in a beaming bright room surrounded by screaming kids and people constantly bumping into the back of your seat.  Her talking about the most mundane and boring topics possible, followed by long awkward silences – for 3 hours.

I’d get talking about something and within seconds “la la la” awkward silence.  I even tried to move the date from the terrible dessert bar to a Walmart across the street but she quickly nixed that idea.  In the middle of another silence-spell I did the old “clap, welp I guess we’d better…” only for her to engage in another mind numbing try at conversation.  But soon after she got the hint, we walked out front, said “later” to each other and that was that.

Saturdays date was at least fun, this one started with the usual messages as well as a phone call that went really well.  We met in her part of town at a jazz bar but as we entered the place it must have been “live country music night” because that’s what we ended up with.  We each had a drink here before going to another more relaxed bar further down the street.  She was lots of fun, good dialogue, sexy, unique and flirty.  On 90% of my dates I opt not to drink, but this one I did – and when I drink, I tend to get a little “touchy feely”.

We eventually found ourselves wrapped up in each other walking down the street and spoke many times about catching a play together for date #2, but that coming to fruition is yet to be seen.

I know one thing, 3 dates in one week is simply too much for me!  Its now Sunday and aside from a little fun last night my weekend has essentially been wasted.  Dating this much is a full time job and considering my humble beginnings on Tinder a few months ago I never envisioned it getting this crazy.  In just 3 months I’ve met 15 women and only went for a second date with the very first one because I took it more serious when I started.

Have any of the 15 been long term material that I overlooked?  Maybe, but I am not so sure.

Moving forward I am going to be utilizing my gut instinct more as it has been right multiple times.  If we don’t chat about anything interesting pre-meet, then there will be no meeting because statistically nothing changes in person.  I’ve also noticed that the ones with more “build up” tend to be better dates and more fun than the ones where we meet after just a few messages.  Basically, if there isn’t a connection made in the pre meeting stage, there wont be in person – it’s just a waste of time and energy.

So going forward I’ll be making a few changes in hopes of having some better connections and not just “dates”.