The 5 Worst Things To Talk About During A Date


Time to blow the dust off the keyboard, for weeks I couldn’t even get in here as I lost the password.  I’ve noticed almost nobody has been blogging much, but I have the urge so lets go.

#1 – Your Ex.

This one is a no brainer for any veteran dater but during my dating tenure it was a very popular topic for the newbies.  If your date brings up their ex – 99.9% of the time all it means is that they aren’t over them and it’s the biggest red flag that can be waved.  Your date wants to hear and learn about you and not much else.  If you feel the need to bring up your ex, you shouldn’t be out on a date in the first place.

#2 – Your Job

Obviously you are going to bring up what you do for a living, but don’t dwell on it.  Shop talk is extremely boring and can suck the life out of a date within a couple of minutes.  Many things can also go wrong  if you don’t particularly like your job, so now the discussion has turned depressing and negative – or you can come off as a conceited douche, both are date killers.

#3 – Your Trip

“Oh it was so beautiful, and the rooms were gorgeous” – who cares.  If it ain’t about you, make it about them.

#4 – Politics or Religion

I’ll give this one a 50% chance of success if you happen to be into the same political party or religious beliefs, but if not – prepare for fireworks, and no call back.

#5 – Mindless drivel

Things such as, but not limited to: weather, traffic, routes you take to work, air travel, personal drama, current affairs etc.

If you want to make a connection on a first date you aren’t going to do it by scraping the surface with worthless small talk.  Ask questions about your date to open them up and see who they really are, if you relate to something then touch on it.  Men on first dates are only supposed to ask questions and keep the female talking for 80% of the date, but they have to be the right ones that get below the surface.

If women find themselves on a date with a guy that only wants to talk about his job and the weather, save the date by asking him questions to take the conversation deeper and more interesting.

Deep conversation is sexy, make it happen!





The Shape Shifter

30s dating

This was the first date back in action, we met on Match.  Her pics were good, she seemed really cool and after about a week of messaging we decided to meet up.

I drove over to her area on a Friday evening and awaited her arrival at the coffee joint.  This was actually the first time I’d arrived early and had to order for myself.  After about 10 minutes she showed – pretty face, but bigger hips and thighs than I had been expecting.  I like curves, but not chubby, pudgy, stocky, “a few extra pounds” or whatever else you might call it.  I am a slender guy myself, so this is just natural.  I am not looking to be like Kermit and Ms Piggy here either…

Anyways, I figured we’d have a coffee, probably grab a beer and that would be it.

We went to bar #1 which was way too loud and busy, so I asked if there were any around where we could play pool or video games.  There was, right across the street.

Drink, drinks…..more drinks

We’re making out in the middle of the semi-empty bar, like idiots.

I suggest going back to my car, we do.  More making out ensues, then we go into the back seat…no sex, but pretty much.  If you know what I mean.

Now I walk her back to her car “Are you going to at least ask me for my number” -oops, all the previous convo had been on the site alone.  So I do.

We text a few more times during the week and we decide to meet up again the next Friday.

I pull up to her place to pick her up, she invites me in, I go inside.


Who the F&%^* is this???

She looked way bigger, shapeless, way less stylish, not sexy at all and overall just…. Tired.

I mentally check-out right then – but we still went on our planned dinner date, which was quick and filled with awkward silences.  We then stopped at a bar for beer – not even that helped.

Oddly enough I think our female waitress had even figured it out, because when my date went to the washroom I motioned her to bring me the bill and the debit machine.  She brought that thing over quicker than a lightning bolt and quickly entered everything, while constantly looking over at the washroom door – almost like I was going to pay and then try for a hasty escape!  Ha!

No, I am not that shallow.

Then as I pull up to her place she invites me in for a beer, followed with “but you don’t have to”

I go in and she gives me a beer, before she curled up on the couch, certainly expecting part 2 of what went down on the back seat of the car.

Me to myself: I can’t do this.

I briefly explain to her that I am tired and should just hit the road – and I did after extremely awkward small talk while putting on my shoes and jacket.

Haven’t heard from her since, I am sure she got the message.

On another note I have a half dozen others already lined up, so we should have some decent content coming up.


The Flight Attendant

30s dating

This one was a wild card, she had pictures on her profile of her laying on a beach in a skimpy bikini, labeled 2013, yet other photos on there as well where she clearly did not have that same 2013 beach body.  Her eH “can’t stands” was a man who was sex obsessed – yet later on in conversation she said someone to be intimate with was one of her main criteria.  Ok, I’ll roll the dice on what I thought for certain was a nympho.

Also side note – what’s with the groupings I’ve been dating?  Teachers, business women and now airline related chicks – weird.

Anyway, we never spoke on the phone but would usually text daily.  I was really quite standoffish on meeting this one, by now I know you always trust the worst picture and there was really just not much attraction.  Regardless during a text convo she was hinting so hard that I just had to set the date, which was last Friday.  I’d tour to her part of town.  Me thinking I would leave my car on her street and we’d just walk somewhere close.  Couple drinks, walk back, go home – simple.

So there I am, parked and I text “I am parked on the street” – she replies “pull up, you’re too far down” – then “do you want to come in for a bit”

Keep in mind she lived with 4 other women, so no, I wasn’t about to head into that court room – I hadn’t even seen her yet.  I politely declined.

So I pull up and there she is on the sidewalk wearing a skimpy black dress and she hops in my car.  Attraction, as I figured, was negligible but she wasn’t going to rely on her looks or her dress, oh no, she had her dress hiked up her thighs and I calmly told her “you look good” as she slithered around in her seat being as sexy as she could.  We tried going to a spot of her choosing but there was no parking, I got sick of driving around in circles and just said “can we just maybe go back to your area?”  As she agreed and apologized for the traffic, which clearly wasn’t her fault.

On the way back to her place she said I could park in her condos designated parking spot, and that none of her roommates were home for the night.

I can see where this is going…..

I then said I would have come in had I known she was there alone and we laughed about that as we walked over to a pub.  There we had 2-3 drinks and then I said maybe we could get out of there and go somewhere else, but since I was driving there would be no more boozing for me, and at this time she tells me she has to work in the morning, which she may have, but I am not so sure.

Anyway I steer us back towards her place and she started holding my hand, and then came onto me in full attack mode with lots of tongue, biting and lip sucking…

We got back to her place, continued doing what we were doing but when I’d try to steer us up the stairs she would put the brakes on.  “We have to save that for next time” –
“I am not sleeping with you on our first date”.

This did seem odd, even crazier was the fact she seemed to intentionally open the front and rear blinds to put our little make-out and groping show on for her neighbors.  And that’s all that would be happening, after my repeated attempts to seal the deal she was blatantly using sex as second date bait – but from the 5-minute mark, there wasn’t going to be any second date that involved me.  She probably knew that…

“til next time




Med girl #2


Blog #23

I am writing about this one just after getting a “Dear John” text message which marked the end of this fast and furious “relationship”.

I don’t even think we had “known” each other for more than 2 weeks and that included the dating site intro, texting, phone call and meeting which was to lead to another meeting which ultimately didn’t happen.

We chatted on the dating site first and she was full of energy and seemed very motivated.  On top of that this girl seemed very aggressive in pursuing me and this came across as a little freaky.  However, she was new to this whole thing saying she had enlisted with online dating less than a week before we bumped into each other.  Right off the bat I figured she was likely just overwhelmed with all of it or felt she was simply excited because she was convinced she had met Mr. Right.

It was her idea to move things to text because she was getting “inundated with messages from men, that she couldn’t reject fast enough” and that texting would be easier than sifting though all the messages to find the new one from me.

Things like that – I’d never heard before, this lady meant business.

We eventually called each other after the texts became too long and tiresome to type – within 10 minutes – “We have too much to talk about for texting”, she said and the phone call went really well.  She was funny, interesting and really pulling things together that we had in common.  She wasn’t letting the chips simply fall as they may, she was physically pulling pieces together to make this work – if that makes sense.

Regardless we had arranged to meet by her place on a Thursday night and she was going to take me on a walking tour of her area.  I thought it was a great date idea and couldn’t wait, until it ended up pouring rain the day we were to meet up.  I had sent her a note saying I hope the rain stops and then she replied that we could always postpone.  I replied when would we postpone to?  Which she replied with “That was a trick question, a little rain isn’t going to scare you off is it”

No, it wasn’t and we changed the date from the walking tour to playing pool at a pub.

The night before we met she had also called me from a very noisy bar after her favorite hockey team had won a game.  I couldn’t even hear her, and honestly thought it was a little weird.  “You’re missing the party” “mummble mummble mummble” “ok see you tomorrow”

Hmmm… I chalked it up as alcohol driven and possibly cause for concern, but whatever.

The next day we met in the parking lot, she actually looked better than her pictures and we shared her umbrella to the pub.  We had a few beers there and played pool before heading to another spot for live music and a couple more drinks.  No denying we got along well, this wasn’t like a typical first date and nothing like an awkward first coffee date type thing, this was fun!

At the live music spot I did end up with my arm around her (liquid courage) before we left as she had to be at work very early the next morning.

Before I had even made it to my door I had received a text from her saying she had such a great time and maybe we could meet that weekend to watch fireworks under the stars, and how it would be romantic.

I told her that was a great idea and we’d make arrangements closer to the day.

That was today.

This morning I texted her asking where and when the fireworks were?  She replied right back saying she was looking up the same thing – but neither of us could find any info on where they were happening by her place.  She then said maybe we’d just get together tomorrow night and watch the hockey game, to which I said that’s a work night and tonight was still the weekend.  She said “for you” as she had to work the next day regardless.

I said I’d come see her when I had to work the next day, and she didn’t, to be fair.

Then she said Ok we’ll hang out tonight but she’ll have to find another date to do the hockey game with the day after.

I said I can probably do the hockey game too!

She then said her friends will be jealous and I can’t “hog her all the time”

I LOL’d that as the joke I thought it was and left her to her work.

About 2 hours ago I got a long text from her, something along the lines of “I can’t see you anymore, I’ve only met you once and I already feel smothered.  I feel you deserve someone that has more time for you”


After pacing around for awhile wondering what had just happened I sent a reply.  “I was only showing availability, and I am sorry it went down like this, take care :)”

And that was it – unless I get a drunk dial from her after the hockey game tomorrow, that is.

‘Til next time





How to deal with dating rejection

30's dating stories

Blog #17

I’ve been on a lot of dates over the past few months and if I were just out there dating and not learning anything from it (or at least writing about my dates) I’d probably go crazy.

I’ve also chatted with many people about dating since starting this blog and the most popular aspect by far keeping most people away from dating is the inevitable rejection that comes along with it.

Rejection simply doesn’t bother me anymore, at least not as much as it used to and the following will explain why.

First things first if you are embarking on a journey of online dating you have to mentally replace the word “dating” with “meeting”.  Online dating isn’t like normal dating where you go out on a date with Sally from your gym or Mike that you met though a friend – not even close.

You’re meeting SweetyGirl434 that you sent a couple messages back and forth with and maybe spoke on the phone with once or twice.

You have built this person up in your mind to be what you want, and they have done the same for you – this happens and is the “leading cause” of what we call dating rejection but there is far more to it.  If you’ve read about my dates you’ll see how many times I met girls that looked nothing like their pictures so I rejected them, obviously, but that’s too easy, lets dig a little deeper.

I’ve also met ones that had great pictures and an even better write up, I anticipated their next email or text with outlandish enthusiasm because we got along so well – just to later meet her and deflate as fast as a punctured blimp.  Zero chemistry “not my type”.

Your easy out is obviously when you don’t jive with the other person that does jive with you, this is when you get to be the schmuck – congrats, but this is a two street and you will get run over.

Here’s the run down:

They like you, you don’t like them – Easiest

You don’t like them, they also don’t like you – A little sting

You like them, they don’t like you – Stinger

Let’s deal with the stinger!

How could they not like me?  We chatted about everything, we spoke on the phone for hours, I had 12 pictures up – what the hell is wrong!!!  Nothing.

Lets wind back to the part how online dating is really just meeting random people from the internet – are we to assume that we are going to have an emotional connection with such a vast number of the random public?

Oh but you had 14 pictures up, a witty write up that took you 2 minutes to write and you both like traveling, reading, watching movies and hanging with friends.

You do realize that everyone likes those same things…..right?

Online dating is essentially akin to walking through a shopping mall and pulling any random member of the opposite sex that you find attractive into a coffee shop and sitting down – now think of the numbers involved to find one that’s going to be compatible, on both sides, to really work out.

For some it only takes attraction – but generally people are done basing relationships on that somewhere in their 20’s.

Online dating is also a huge marketplace filled with able singles, for some it only takes one off putting thing from you to send them back to their computer where they can meet someone else in a few clicks.

Online dating is far from perfect, but the “rejection” from it really isn’t true “rejection” like getting fired from your job or dumped from your long term significant other.  People get rejected several times a day dealing with normal life things that we don’t even notice and online dating rejection shouldn’t be looked at any differently.

The Teacher (first of many)

30's dating pic

Blog #10

The first comment I made to this one was in regards to her dog, which looked very similar to mine.

I really was just asking about her dog, as this one was HOT (or I should say, had hot pictures) and I usually don’t bother with girls that were as smokin’ as this one portrayed herself.  Oddly enough, she responded very enthusiastically and we ended up chatting quite a bit.

It turned out that she had worked just around the corner from where I use to live (twice, two separate towns) for years and on top of that we had an endless amount of weird similarities to keep our communication fresh and fun.

We sent many daily long emails – with her inserting questions at the end of each one for me “Where do you see yourself in 5 years”, “What makes you laugh” and about a dozen others.  From the tone of her emails I predicted a very serious lady, that had no time for BS, but was also laid back, cool, smart and funny.


Then she called me, wow.  She spoke at about 550 words per minute, bounced from topic to topic (about herself, I was just there to listen apparently) which was hard to hear over her blaring TV in the background and constant interruptions from her family (didnt live alone).  I was truly shocked at how wrong I’d been in my assumption of who this chick was, but those pictures – I had to meet her!

We set the date at a cafe on a Saturday night, and as always I was there early to wait for my prize..

She pulled in, car stereo pounding and I sent her a text “Is this you?”

She responded with “I am here, are you the Philippino woman in the car behind me?  LOL

We met and hugged in the parking lot and she carried herself well but was at least 30% off from her pictures, maybe 40.

She wore a thick layer of cover-up that actually worked to accentuate the imperfections she was trying to hide, which were multiple and she wore a multi-colored jacket that really wasn’t doing anything for her.

Regardless, we went inside and grabbed a couple teas before settling into a nice dimly lit corner booth.  I asked her if she wanted a treat or snack to go with her tea, which was when she told me she was on a strict diet and pulled out a Tupperware container full of some rather smelly “health food” that was adequate for her diet due to long standing intestinal issues.

Showing nary a concern for getting us kicked out for bringing in outside food…

She talked, a lot and about a lot of things you aren’t supposed to talk about on a first date – and those were her ex’s, some that she hadn’t seen in over 6-7 years..


Like the phone call, I had to fight to enter the conversation and steer it back on track.  “Oh yes, his mother and I were very close (blue car drives past) -pause- I like those cars, anyway, his mother…”


Regardless, we closed the place down at midnight and made our way out to the parking lot.  She swung around towards me and said “I really enjoyed our conversation” so I grabbed her, hugged her and kissed her – on the cheek.

Earlier in the date I had mentioned a doggy date at a dog park, I’ll bring mine, she can bring hers and maybe we could do that at another meet-up and she liked the sound of that.

I texted her the day after that I had fun, and she replied “Glad to hear”.

It’s been over a week and I am still not sure where to go with this one….

Online dating in your 30’s


So here we are with blog post #1, which may or may not be a lengthy series going over my dates.  I am an average looking, single professional, 33 year old guy in a large city.  I am using online dating sites (we’ll get into specifics later) which all spurred from a short stint using Tinder a couple months ago after hearing that the Olympic athletes were using it in Sochi.

I had previously said I’d never online date, but thanks to Tinder here I am.

Going on two months in I’ve already met 8 women from the cyber bar and each is and has been unique.

I am learning too as I go, I am not an expert at this, but I welcome you to share in my destiny, which includes misery in my journey to find a mate from online dating.