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 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….