The Cougar Rejection


For awhile there I thought it was advantageous to date women that were older than I.  Not incredibly older (I am 33), but ladies in the 35-38 age-range seem to like me (or I should say, seem to like my dating profile).  I had two of these on the go at the same time, one 36 and one 38, this is the story about the 36 year old.

The 36 year old made me her favorite on the dating site and liked a couple of my pictures and she was truly a knock-out in the looks department.  Our chats were playful and fun which quickly moved to daily texting.  I had gone for the meeting pretty early on, but she was always busy with work, family or “life”.  She almost lost me after we’d agreed on a time to phone each other, but all I got was a text “I haven’t forgotten about you, currently grabbing coffee with a friend after yoga”.

No “sorry I can’t chat tonight” – all I got was the message above.  Keep in mind, during this time I was head-over-heels with the build up date girl, so interest in this one was minimal at best by now anyway, which was around 2 or 3 weeks past our first chat – still no meet, and now not even a phone call.

However we did finally agree to meet on a Sunday afternoon for coffee (the day after the build up girl flop) and my hopes of anything more spectacular happening were very low indeed.  I got to the place a little late, parked the car, texted her that I was there and ran inside.

I looked around and saw nobody fitting her description..

I then went back out the parking lot and texted her “I think I am at the wrong location”

Turns out I was at the right location, she was up the road at the wrong one.  She said she’d drive down and meet me after apologizing..

This was when a new white BMW pulled in, it was her, and she was even more gorgeous in person.  We went inside, chatted for hours, laughed and had fun before being told the place was closing and we had to leave.  During out chats she had suggested second date ideas, and I quickly agreed to them.

Then in the parking lot she asked not once, but twice, “we’re going to stay in touch right?”

Me: “YES!”

I left there on cloud nine – could this be the one I’ve been waiting for?  She was hot as hell, cool as hell, had a killer job, own home, nice car, we got along awesome – I was literally ecstatic.

Two days later we were texting again, just as playful as we had been before and I asked to meet up with her again the following weekend.  She said that it was too early to make a call on that as she had family visiting from Europe and she’d likely end up showing them around.  We texted back and forth a few more times and then one day she didn’t respond.

I didn’t really think anything of it – she was indeed way busier than I was and also had family visiting.  We didn’t text for over a week, and my gut told me this wasn’t good, so I sent the “feeler text” to see where things stood.  “Hey you, did you have a good weekend?”

And I got back what I pretty much expected – I am a great guy, easy to talk to but she’d met a guy a week after me and felt he was a better match than I was, and to take care and be well”

I didn’t respond – but I don’t believe her either.  She had told me about using that excuse during our date regarding a guy that was begging her for a chance and wouldn’t stop sending her messages.   I was also just on the dating site to delete her messages and saw that she’s been on today as well.  Why be on there if you’ve just met your epic soul mate a week earlier?

Better yet – how could you go from 2nd date ideas and begging to stay in touch to pretty much “leave me alone”.

I’ll never know – but the fact that she was divorced might have something to do with it


The Banker


Not long after I began chatting with the VP, I also stumbled upon a late 30’s banker which I honestly didn’t have the highest hopes for.  She had a very bleak dating profile that only had one picture and I got the vibe that she put it together in about 5 minutes.  We sent a few notes back and forth and then went right for the date – no phone call involved.  The date itself had to be delayed by a week as she was in Europe on business but she messaged me the day she got back and we set our meeting for Saturday afternoon drinks – this one caught me by total surprise.

We met on the sidewalk and as she came walking up to me it was apparent she was looking far better than her picture had led me to believe, her body was fantastic as well and we went into the pub for round #1.

Chemistry was instant, conversation flowed endlessly and it wasn’t long before we decided to get out of there and go somewhere else.  We ended up on a romantic roof-top patio and ordered drinks and several hors d’oeuvres.  We then ended up on a couch together and just continued chatting (and flirting) until the sun went down.  We left that place and went exploring again until we found a spot with live music – good live music – $15 each cover charge live music, which she abruptly paid as I only had debit.  She also got the drinks inside.

We stayed there for around 2 hours (now around 1am, date started at 7pm) and we decided we better call it a night.  On the way to the live music we had passed by her place and she described it to me in full detail.  I responded “And you aren’t going to show it to me?” – Her: “Nope!”

She was a good girl.

On the way back, again in deep conversation, she stopped and said “Well this is me” as we were standing in-front of her place.  We tightly hugged, kissed, hugged again, kissed again and then hugged again.  Her clearly beginning to go weak in the knees – knowing the front door was right there, but she held her guns “I am going inside and you are going home” and with that we told each other how much fun the night had been and parted ways for the evening.

When I arrived back home I had a text from her again thanking me and letting me know how nice our evening was together, and I sent one back relaying the exact same message to her.  I let a couple of days go by and then asked her out again this coming weekend and she agreed…

To be continued….