The 28 Year Old

I usually don’t date women under the age of 30, I just tend to have more in common with the ones that have been on this planet for a similar amount of time as I.  However, exceptions can be made, and I did for this “waste no time” 28-year-old that reached out to me first.  She asked to meet after the second message and I was more than happy to oblige.  We exchanged numbers and all I sent was “see you there at 8pm on Thursday”.  She replied “see you soon”.

I met her in front of the coffee place (her idea).  She didn’t really look like her (vague) pictures, but close enough, and that seems to be the norm – and I get it.  She’s blonde, about 5’9″, in very nice shape, conservatively dressed, minimal – if any – makeup, she didn’t need it.

She jumped right into how she’s trying to start her own business, we get our teas and have a very nicely flowing conversation for about two hours, then she asked if I’d like to go for a walk – sure!

She’s Ukrainian born and lived most of her life in Italy but moved here in 2005 and plans to stay here forever, even though she does still bounce back and forth, getting in from Spain just two days before our date.  She asked me to walk her home and then I’d jump on the nearest subway and head back to my place.  Throughout the date she was dropping hints all over the place, like, “well you’ll have to show me how to do that”, “can you take me along next time?” – lots of things instigating future contact.  When we arrived at hers she says  “well maybe we can go skiing together, or jogging”

Skiing, WTF?  (Its Spring time)

I gave her the old “ass out” hug and went on my way.  She’s nice but I just wasn’t physically attracted to her, she came across like a business partner and not a love interest.  However, I am done with tossing potential friends aside after these dates.  I’ve mentioned before that I believe dating sites use an algorithm more or less to be friends than anything else (or worse, an algorithm designed to keep you paying and going on endless amounts of first dates, but that’s another post)  – and my gut tells me she’s on the same page.  I’ve learned from all this dating that 9 times out of 10 they feel the exact same way you do.






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….