3 Date Week (system revamp)

sex dating toronto

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”.






Sales girl #2 (death in the family)

30's dating stories

Blog #18

Sales girl #2 sent me a message first and we quickly got into an instant back and forth conversation about various things – most being her strict requirements for a potential match.  She had one of those profiles that lists the things the guy has to do or have and not so much actually about her.

There would be no “endless back and forth e-mails” nor would she allow me to ask for any additional photos of her (something I never do anyway) and she wanted to meet quick to see if there was anything worth pursuing.

Fine by me…but I was definitely dealing with a hot head that had been through some bad online dating experiences.

We sent 5-6 messages back and forth through the dating site before night fell and I didn’t get a response from her to my last one, I figured she’d get back to me the next day and left it at that.

The next day I never heard from her, but the day after I was notified that she had “noticed me in her daily matches” (liked my picture among other guys pictures) but still no response from her to my last message.

A couple more days went by and still nothing – this was odd, we definitely had a great conversation the other day and its very rare for girls to just up and vanish like that after showing interest as she had.  Regardless I ended up chatting and dating others and eventually forgot all about sales girl #2.

..Until about 2 weeks later.

She sent me a message that there had been a death in her family that was pretty serious which was why she’d been absent and she was wondering if I was still interested in meeting for a coffee sometime.  I responded that I was very sorry to hear of her loss and that I would still love to meet her for a coffee – before asking how she was doing, really?

She said that her Dad had died last week from cancer.

I instantly began feeling very sorry for her, first off, she was clearly having issues dealing with what had just happened and was maybe looking for a date as an escape.  I said that if she’d like to get out of the house I would drive over to her area and meet her for a coffee.

She agreed and we’d meet in a few hours.

Of course I was wondering if she was lying about the death – but what 30 year old would lie about something like that?  No way…she’s clearly just looking for a change of scenery or more likely her fathers death hasn’t even hit her yet.

I drove over and got to the parking garage pretty early, we were meeting at 4:00 but I got a text from her at 3:45 that she was there and got good seats for us, I messaged her that I’d be there in a few minutes and walked over.

As I walked in I saw her sitting and looking pretty good, she welcomed me with a big smile and a hug, before pulling out her purse “I have some change for coffees” before I assured her that I could cover it with a nice laugh and told her to hold the seats while I went and got our drinks.

As I came back she quickly jumped into dialogue – which were mostly questions for me.

Keep in mind there was a 30-something woman sitting alone about 5 feet away clearly eavesdropping on every word  – to the point of looking at her while she asked a question and then directly at me for the answer.  This got extremely annoying.  Not only had I somehow landed in an interview-date, I may as well have been on camera too.  As her questions got more outlandish my answers got tamer, shorter and less focused.

Here I go again, anyone else would have bailed, but there was something about SG2 that I found extremely sexy – I wanted to curl up with her right there (even with the onlooker) and spend the rest of eternity peppering her entire luscious body with kisses.

The head attached to my shoulders said no, the other one said yes – this is not an easy battle, ladies.

Eventually the onlooker left and our conversation opened up greatly, but more “friendie” as we laughed and shared prior horror date experiences.  I knew I was cutting close to slamming myself into the friend zone but this girl has just lost her father and it’s really about making her feel better, not me, so I dove deeper.

Albeit very sexy, SG2 was dulling the moment with her know it all mantra about things, “No, I DO know, I am 30″ (exact quote) and every time she was misinformed or blatantly wrong about something I’d have to literally prove what the truth was in the most polite way possible.  She went on about 2-3 ex’s (big no-no), how she was such a city girl (recent, use to live in the country) and went on about her mediocre job.

I smiled, injected dialogue and just nodded my head.

She had said she’d better get going as she had a friend coming over for dinner, but it was one of those endings that just wouldn’t end.  Purse in lap, jacket on – purse back on table, jacket undone, a few times.

I then got up and said “shall we” and we both exited the cafe and faced each other on the sidewalk – I gave her a big hug (which I think she thought was going to be a big kiss), told her she should take some time to herself and not run back to work so fast.  Take some time to herself, get away, do something fun, relax, whatever.  I even said dating right now probably isn’t the best idea, but told her she had my number and can call me if she ever needs someone to talk to – she melted when I said that and she told me I was “so nice”.  I told her she was a sweetheart and to have a good night, as I turned and went for my car.

I was initially going to wait 2-3 days to send her anything but I figured under the unique circumstances I’d message her the next morning, which I did, by simply asking her “So what did you think”

About 30 minutes later I got a reply stating that she sensed a strong “friendship vibe” from me but I was such a great guy.

I politely told her I enjoyed our conversation and to take care and be well 🙂

That was it.

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.

Video Girl (Zzzzzz)

dating in your 30's

Blog #16

I had fairly high hopes for this one initially – and I even told my mom about her.

Mom, she likes old cars and sailing..

“That’s good, make sure you get an outdoor girl, you want one that’s active, if she likes sailing that means she likes to be on the water, she sounds good”

Now this was odd because I am really not even an outdoor guy, and although we have a spot on the water I rarely even make it up there.

“ok Mom”

I am not sure who made the first move but we were sending messages back every day or two.  Her photos were ok, her write up was ok and her responses were “ok”.


A glasses wearing brunette standing about 5’6″ with a little hipster vibe going on.  Jeans and dark green jacket type chick from a blue collar town now living in the heart of the city.  A pubber, not a clubber, in her early 30’s.

This could work for me if there is attraction – I know her type and I know it can, let’s see….

She asked if we could talk on the phone, no texting, she wanted to go straight to the old dial and ring – which I welcomed.

I called and she spoke with low energy and kept the topics pretty mundane – nothing jumped out and bit me or evoked anything resembling urgency to meet this girl in person.  There’s another word for this, boring.

Being me though, I always give the benefit of the doubt to them and hold out thinking in person she could be a hot little bomb shell that makes me go crazy for her, so I asked to meet and she quickly agreed.

She said she could come to my area “the next time I am passing through on my way to visit my parents which is usually once a week” but I said I’d be more than happy to come to her, as a guy I feel that’s kinda my job anyway.  We set the date for the next Saturday at a nice cafe around the block from her pad.

Good thing I left early as traffic was beyond brutal and right as the clock hit 7:00pm I was in my car at the traffic light looking at the cafe to my left, and here was VG looking at me as she walked across the street on her way into the cafe, before we both quickly looked away.

She was wearing a long tweed jacket doing her best to cover up her body (I assume) but I could tell she was very top heavy.  Something you couldn’t make out from her pictures, even full body shots.

I am not saying top heavy as in nice boobs that make you wonder if they’re real or not, I mean top heavy like HUGE boobs that belong on a woman weighing 350+ but attached to a girl maybe weighing 150 with a tapered lower section.


Too bad I am an ass man 😦

I parked around the corner and met her as I walked up to the cafe, quick hug and greetings before we entered, sat down, ordered our coffees and got to talking.

Just like the phone call her dialogue was low-ball and anti-stimulating, but her eagerness with it (even when I purposely let awkward silences roll) told me she was interested, but I wasn’t.

I had finished my coffee fairly early and was really just riding this one out between mumbling mindless responses to her  and wondering about the girl I’d dated the night before.  Anyone else would have made an escape but I suffer from a disease called being empathic towards another persons feelings, so I suggested we hit up another spot (before I fell asleep).

We walked down the street to another place she mentioned, but when we got there it was closed.  We went into another place and ordered up two more coffees..

This was when she went to the washroom and I checked my phone to see a message from the girl I’d been on a date with the night before asking me how I was.

Now I really didn’t want to be there.

During my coffee I went to the washroom and replied to the message, came back, finished my coffee and told VG I’d better hit the road.

As we walked out of the cafe I pointed in the direction I was parked and turned around to see her standing there like a puppy dog.

I went back, gave her a big hug, told her it was nice meeting her then turned and went for my car.

I never messaged (nor heard from) her again…









The Sales Chick (Push and pull)

30s dating

Blog #15

We’ll call her Tammy.

She sent me a message on the site and after going back and forth just a couple times she asked to “Take this to BBM” (phone to phone messaging) and I obliged.

On just the second day of messaging one another, and the first using BBM she was sending me pictures of things she was doing and places she was.  I found this fine – I didn’t mind, nor did I have anything better to do, but still, I thought it was a little weird.

I took it as a sign that she was light in the “friend department” and probably just enjoyed chatting and sharing things.

Her pictures looked pretty good, she had a good job, a new car and owned her own home – she certainly had her act together at 34 but even with the close communication, she never opened up like most of the others did.  She wasn’t guarded or secretive, just sorta’ quiet…

Not long after this I started asking when she’d like to meet up for a coffee but she was a pretty busy girl working long hours, driving a long commute and in the midst of buying a second home that was closer to her workplace.  I told her that I understood and to just let me know when she’d have time to meet.

I think it was during the second week of messaging that she told me she would be able to meet that Friday evening after work, around 6:30 at a coffee shop local to my place.  It was set.

The messaging at this point had slowed down to a crawl but we usually sent one or two per day leading up to the date, I think some days even went by without any.  From my experience this is a De-attachment process – to make the entire thing quick release when the meeting goes poorly.

To me this is welcomed at this point in the dating game 🙂

At 6:30 that Friday I drove over to the coffee shop and sat in my car, 6:30 came and I didn’t see her.  I sent her a note at 6:40 and she responded “OMG I thought we were meeting at 7pm!?? I feel so bad”

Now, at the time I had another date the day after this one at 7pm so I was a little confused and told her not to worry, but after checking later we never re-scheduled for 7pm – at least not that I was aware of.

Seeing as she was going to be at least another hour, I went and got something to eat and waited for her message letting me know she was on her way as she’d been held up at work.  She said she’d “explain when I get there”.


Fast forward to 7:30 and I am back there waiting, and she pulled up.

I met her at the parking meter and small talk ensued – she was late as she had been making offers on houses with her agent and quickly broke out her phone to show me pictures of them all and let me in on the details.  This took us from the sidewalk into the coffee shop, through the ordering process and into our seats.

Visually she was attractive but not as good as her pictures (100% normal) and came across as cool, funny, smart and kind.  She complimented me countless times on several things and we eventually closed the place at midnight.  We chatted a little by our cars, hugged each other and left.

Her saying “see you soon” as she got into hers..

I drove home, chalked it up as a good date and set into the “wait to message” mode.  The date was Friday and I was going to give her some time to think before I messaged her on Sunday.

The day after (Saturday) I had a date with video girl (as you’ll read about) and it was during that date that Tammy sent me a message

“Hey you, how are you? They accepted my offer on the house!”

We messaged each other back and forth (yes, I sent a couple while on the other date :/ ) and when I got home I shot her a note “When are we going to see each other again”?

She responded that she wasn’t sure as she was very busy but she’d get back to me.  The day after and I think even the day after that we sent each other notes but after the one night neither of us has engaged since.  I am not going to because the ball is in her court – and after thinking about it, I am simply not as keen on her as I may have been before.

As far as her – I have no idea what happened, maybe she is busy – but most likely she took the anti-rejection as a self-esteem boost and went to apply that energy on someone else, who knows..


I still have her in my BBM list (for now) – time will tell!

Update: About a month after our meeting I noticed she had blocked me on eHarmony, so I removed her from my BBM list.


Till next time






Teacher #3 (The builder upper)

30's dating

Blog #14

“So and So has sent you a wink”  was the title of the email I had been sent to let me know that someone was interested in one of my dating profiles.

I opened it, and saw a cute little head shot of a smiling brunette – “not bad” I thought..

I went into the site and checked out her profile that had 5 pictures.  Head shot, Head shot, Head shot, Head shot, Head shot.

I made a comment about something in the background in one of them and she replied with something witty and pretty funny..

And that’s how it started.

Now let me first state that at this point I have learned something about online dating and how women often portray themselves, but this one started before that knowledge was concrete regarding photo trickery and other tactics dependent on the situation and female.  However even then this particular one stood out from the others..  She was either trying a totally new approach or was simply new to this, because she came across wholesome and fresh – believable – and funny too.

I scanned the head shots as much as I could to try and make out a body style.  Her profile description said “curvy” but we all know that term gets thrown around pretty loosely these days.  Not long after initial dialogue I asked her about it and she said “well, I looked up curvy girls on Google and that’s what I am, I am not blubbery” – and with that I decided I’d take a chance on this one, helped immensely by her humor + personality + occupation and assets = that oh so attractive.. drive

Ding Ding, pass go and collect $200

This one started during and after some of the others so I was busy with the texting and messaging of several girls and sometimes she dropped to the bottom of the list, but she made sure to let me know about it, daily.

“Am I old news?” got tossed around once or twice as with comments regarding “the other girls”, to which I kept quiet.  But once the previous teacher date was done she was the list topper, helped largely by her constant communication and non intrusive but odd/interesting questions or chat topics.  She’d also let me know little things during texting like “GTG for now, at work” or “sorry for the silence, I was driving home”, that stuff adds up, especially when you know its true.

However, as I got more involved in talking with her, she got a little too involved – to the point that I was clearly more than an 80% chance one date wonder which is how I view these things.  To her I was 110% “pretty damn sure” going to be her next long term squeeze but she sure sent an array of mixed messages to go with that.

“You may projectile vomit when you see me though” – “I need sex, come see me” – “Do you like blowjobs?” – “I am not having sex with you the first time I see you” – “I am looking for long term” – “You’d make such a good FWB”


I couldn’t quite get my head around it either, but I learned that some of the more raunchy ones were sent when her other hand was operating a vibrator, so I learned to chuckle at those ones and not put much weight into them.    7-times in one day was her record, helped by I don’t even know because I never sent her anything with erotic intentions.  Little things like me typing “I like curves” would set her off, apparently.

Keep in mind I still have no idea what her body type is at this point, she could be 400lbs for all I know – so I am really trying to keep my reservations about the whole thing but have also accepted the fact that she isn’t going to show me a picture, I am going to have to go meet her – and she wants to meet at her place.

Yes, date #1, at her home and we’ve never seen each other or met in person before.

What. Am. I. Doing.

Now I know what you’re thinking, and I thought that too – I am a guy after all.

But those thoughts were mostly dashed with “We can’t have sex the first time, it’ll ruin everything, I purposely didn’t shave my legs” (to which I asked how bad they were, and she said not bad 😉  So whether sex was her intention or not, she made it very clear that she didn’t want to do that on our first visit, and honestly I am not even a one night stand type of guy.  My main intention was to see if I was even attracted to her.

So I got in my car and drove to her house and sent her a text from the parking lot, “I am here”.

“The doors open” she responded.

The door is open?  WTF..

I opened the door and saw a long staircase leading up to her place, with her kinda hiding at the top…. “hi” as I took my shoes off and walked up the stairs to meet her.

She was big boned for sure, not blubbery as she said – but still a little bigger than I was looking (or hoping) for.  Still, I gave her hug before she nervously said “do you want a tour of the place” – which I obliged.  After a blurry fast tour we ended up back in the living room and she asked me which board game I wanted to play (her idea, which she told me before I showed up) and I said it really didn’t matter.  She pulled one out and then got us a couple glasses of water…

We really just played the game together and chatted for a couple hours – and it was late as I didn’t even get there until 11pm but was putting my shoes on to leave before 1am.  A short meet and greet indeed and very odd to have it at her place.

I didn’t contact her that night or the day after, then I got a text from her saying she was sad that it wasn’t going to be a thing.  Then went into 20 question mode asking why I didn’t like her.

Apparently my body language the night before spoke volumes about not being interested – which I had no idea I was doing, but she’s right (it also explains A LOT of previously unexplainable things regarding others too, good lesson!)

I summed up her question of why with that I didn’t know why because I wasn’t a physics major but I still thought she was very cool.  We sent a few kind messages back and forth and agreed to “stay friends” but its unlikely I’ll ever see her again.




A Bad Date Classic

dating in your 30's

Blog #13

Seeing as I can’t date with this nasty cold / flu thing going on (and have had to postpone my next date twice already) I’ve been thinking of something to post up, so it’ll be about a date that I had about 4 years ago, and oh yeah, it was BAD.

Lets just simply call her crazy lady.

I was on POF back then for a short period with a thrown together profile and was messaged by a girl that was about 3 years older than me.  We sent some messages back and forth and even chatted on the phone once or twice.  She looked fine in her pictures, brunette, curly hair and stood around 5′ 6″ and was “ok” on the phone.

We made arrangements to meet at a coffee shop in the city at 7:30 one summer evening a few days in advance and left it at that.

I made it to the coffee shop at 7:15 and proceeded to stand around waiting for her.  7:30 came and there was no sign of her, 7:45, 7:50 so I sent her a text “At the coffee shop, are you coming?”

I was hit back with a flurry of messages “OMG you’re there, but we never confirmed, did we?” – yeah, we did, on the phone.

She was still at work and said she’d be over as soon as possible.

I waited around until close to 8:30 when she speed walked her way up, half huffing and puffing and we said our hellos.  Our date was set to be one where we’d walk around the city and do whatever we felt like, as long as it didn’t involve sitting across from each other at a table somewhere, to stare at each other “like idiots”.


My initial impression of her was that her 2-3 photos on POF were from when she was in her mid 20’s, but she was 32 in person and there were some differences.

Regardless, we began walking and only made it a few blocks before she told me she was starving and had to eat somewhere, so we dove into a restaurant and ordered some food.  Our plates came but the waitress had forgot to bring us our cutlery – right away she had her hand up, waving around “Ma’am! Ma’am!! (waitress was younger than she was) you forgot our cutlery, how are we supposed to eat without cutlery!”

That was the first warning shot.

Then I notice that what I’ve ordered isn’t what I thought it would be.  I ordered a salad with what I thought was chicken on top of it, but it came with some big slimy mushrooms and sauce all over it.  I ate a little of it that wasn’t covered in the sauce  and she took notice.

Do you not like it? – “Its ok, I already ate, don’t worry about it” I said.

Hand up again, Ma’am!, Ma’am!! He doesn’t like it!!  He doesn’t like it!

They took it back to the kitchen to “remove” the stuff I didn’t like and then brought it back, without cutlery.

Crazy lady now gets up and marches straight to the back, into the waitress area, and while staring at the waitress grabs some cutlery and heads back to the table.

I am in shock. – And so is everyone else in the place, including the bartender situated at the bar to the left behind me.

I refuse to even touch the food now, which has likely been spit on by every employee in the place, but pay for both anyway as I believe we’ve caused enough trouble already.  Now she’s answering phone calls, being loud and making plans with her friend on the phone “after her date”.  I am casually looking around for the front door – knowing that I have to bail soon – before she hangs up her phone and says that since I paid for the food, please allow her to buy us each a pint of beer.


The waitress takes our drink order over to the bartender and he fills up 2 glasses, and brings them over.  He hands one to her, then, with eye contact on me places mine in front of me and says loudly “Get that into you”.

Crazy lady FLIPS “What the hell is that supposed to mean!!” as the bartender walks away laughing his ass off, as well as me.

We drank those and left the restaurant then headed back toward the area where we’d come from – where the subway was – so I could leave.

As we approached the subway stairs and I was about to say my farewells she says “Hey, lets go into THAT bar right there, on me”


We sat right at the bar and she ordered a pitcher of beer and I believe we had two of those.  I was now drunk.

She turns to me, right at the bar and says “I have to kiss you to see how attracted to you I am”

Huh? Right here?


F*ck it – full on make-out session right there at the (busy) bar.

From there I really don’t remember much, except making out with her on the subway platform waiting for the train to come, then her pouting eyes through the doors as I got on.  From the call at the restaurant she had “made plans” to meet her friend after me, but about 30 seconds after the train pulled away I realized that was BS and I’d just thrown away a one night stand with the craziest chick I’d ever been on a date with (so far).

Oh well.

And no, we never spoke again.






The Fallout girl

Gorgeous - but do you have any recent pics?

Gorgeous – but do you have any recent pics?


I have met nearly every woman I’ve chatted with online, except for one (at this point).

Lets call her Kerry.

I liked one of her pictures and was instantly hit up with a barrage of messages from her and then given her number “to text” all within a couple hours – while in the midst of chatting up others and prepping for a date that evening.

Her texts were frequent once I sent the first one and after just a few she was asking “Can we talk later?”, “Can we”, “when will you be able to call me?”

By the time I got home from the date I’d been on with Country girl I was ready for bed, and had to explain to Kerry that it was late and I’d call the next day.

“Sweet dreams hun, can’t wait to hear your voice” came after a few messages of disbelief that I’d actually call her the following day, in which I had to convince her otherwise.

The following evening I called her up and was actually surprised by her coolness – she had a seductive voice sprinkled with witty sarcasm, funny jokes and realism.  This went well with her hot pictures that showed lots of cleavage, expensive dresses and style.

I was on board!

Our texts continued each day as did nightly phone calls.  In all honesty I liked chatting with her more than any of the others, but alas, things weren’t as good as they seemed.  First were the pictures, they ranged from slim bikini-clad poses from when she was likely 21 years old (31 at time of  interactions) and her body heft increased as the series went on, until the most recent one which was a head shot that showed a chubby arm in the way and no collar bone in sight.

Ever heard of the #1 dating profile picture rule for men?  If you can’t see her collar bone – she’s a fatty. (LOL, I am kidding,… sorta)

So okay, she wasn’t all that she used to be, but without actually meeting her how was I to know?  I was still set to meet her the following Saturday night.

There were 3 things that made me call this off, #1 was the pictures and #2 was when she told me that not only was she bi-polar, but she met with her shrink on a weekly basis – the last meeting, just the day before, had garnered her a week off work – because she wasn’t “well”.

Does that make you feel uncomfortable? She asked – “Oh no, its fine” I said, when really I was squirming.

I had dated a bi-polar chick back in my early 20’s and wanted nothing to do with another one, ever again.

Now the icing on the cake, a double whammy for you.  I went back into the dating site the night after we’d spoke on the phone the first time to re-ponder her picture cache, but her profile had been set to private.  I texted her asking why she’d hidden her profile and she responded with “Because I met someone ;)”

Ohh..  ok.

Then the one where I made my escape, the day before our date she texted me that her grandmother had died and that she couldn’t meet with me the day after.  I said I was sorry for her loss, and to take care and be well.

This was likely brought on by my apparent “quietness” during our last phone call, that she asked about no less than 4 times during the brief call, which I am thinking put her into chaos-mode.

The day after this I checked her Facebook and her profile picture had just been changed, smiley eyed and bushy tailed – seemed odd to do such a thing after such a loss.

We never spoke again, however she did try calling me a couple times, texting a few times and sent a final message through the dating site in attempts to re-engage with me.

Close call.




The Teacher (the interrogator)

30's dating

Blog #11

My initial goal when I started dating was to meet 10 girls, then take a step back and ponder what I’d learned (if anything).

Since I started this blog, I’ve decided to meet 30.  #8 so far was another teacher, which is odd because she was the second of 3 teachers in a row – and shared the same name, age and location as the one that followed her (that you’ll soon read about).

We’ll call this one Sara.

I believe she messaged me first, her pictures looked good, well traveled, educated and seemed quite pleasant, at least initially.

After the normal “who are you and what do you do” messages; I went for her number, and picked up the phone when I received it.  Right away she wasn’t what I was expecting on the phone.  Very docile, cautious, reserved – but would strike with off the cuff questions that were frankly none of her business (at this stage).  I sensed something off when I brought up the idea of a walking date and she shot back “You think we’ll make it that far” (walking, after having coffee).

I said, “Uhh yeah, why wouldn’t we”

Keep in mind, as you probably already know, I don’t run out on dates, no matter how bad they are, but this girl had been through some bad ones, I just didn’t know if she ran out on them, or they ran out on her.

The headline on her dating profile was something along the lines of “Its impossible to meet a match online” – so use your own judgement.

She lived about an hour away from me, so we agreed to meet halfway – no way was I going all the way to her with such slim chances for success, even when I have friends that live in her town.

I got to the spot early and she pulled up behind me soon after.  We got out and met in the street, quick hug and headed into the cafe, small talk ensued as we ordered our treats and pulled up seats..

As I drank my milkshake she slowly started prying, again, as she had on the phone.  So when did your parents divorce?  “ohh, hmmm” – “and what affect did that have on you as a child” – No affect, I was young, mom and dad deserve to be happy, no? I replied.

I stick handled my way through 3-4 more interrogation type questions regarding my siblings before making a loud slurping noise as I’d reached the bottom of my milkshake and blurted out “So you wanna go for a walk?”

Which she agreed to.

We went around the block once, I tried to keep the chat civil while she kept prying away at other things – I am still unsure how she figured out my rent was double what hers was, or how she found out my exact birthdate.  Was this chick a high school teacher or CIA?

When we got back to our cars she said “shall we call it a day” – I said yes, we had a quick hug, got in our cars and drove off.

I didn’t really know what to think, she wasn’t attractive (to me) and really came across as just….brash.

She sent me a text later that night, “You’re a great guy, but I didn’t feel a connection”

Gee, ya think?

I said it was nice meeting her and wished her well on her continued search, contemplating telling her to chill out with the personal questions, but, I’ll let her figure that one out on her own.



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….