The roadtrip date Latina


Well here’s one that I thought might just have a chance.  Girl #21 was by far the cutest of them all, one of the coolest and one that I had the most fun with.  Everything just felt natural and I thought it was the beginning of something special, however that wouldn’t be the case.

I had sent her a message on the dating site and we chatted back and forth every night or two.  I sensed a good connection so I offered her my number and asked her to text me if she’d like to move the conversation to that.

That’s when I didn’t hear anything from her.

I figured that I must have spooked her by going for the phone after so few messages so after a week or so I deleted her messages and focused on others.  Then about 2 weeks later I get a random text “Hey its D, you gave me your number awhile back and I am sorry it took so long to reply but better late than never?”

Red flag? Yes – but I figured she had probably been dating someone else and it had fallen through, she was also really hot, so I took the bait and we started chatting away.

We met the next Sunday by her place.  She looked adorable as she walked up to me and we hugged, her body language was also very good the entire time.  We grabbed a bite to eat almost right away and that’s when I was telling her about an amazing farmers market about an hour outside of the city and she abruptly said “lets do it next Saturday”.

Almost in shock I was like – really?

She was dead serious.

In my head I knew it had a very slim chance of happening as our date was still very much in its infancy and just too many things could go wrong.

But nothing went wrong, it only got better.

As we parted ways we made arrangements to meet up the next Saturday morning and then drive down to the market – this was right after a very flirtatious and slow stroll though a large antique shop.  Her trying on vintage clothes, the two of use sitting on vintage furniture together and playfully touching each other along the way.  This had been a very good first date!

After that I didn’t text her for 2 or 3 days, and when I did I simply asked if we were still on for Saturday – she responded “Hey :)… YES!!!!”

I picked her up on Saturday morning and we drove down to the market.  Conversation flowed even better than I had imagined, time flew by and we had a great time.  I asked her several times “Are you enjoying yourself?” and she assured me with big smiles and laughter that she was having an amazing time.  Her body language was even better and more positive than before and she also gave me her business card so I could see that she was “real”.  After lunch and trips through the market and several antique shops we found ourselves back on the highway headed for home.

I pulled up to her car and we loaded in the items that she had purchased.

This was when I said we’ll have to do something even more fun for date #3 and she suggested the local six-flags type park.  We’d ride the roller coasters and it would be a blast, but she reminded me that she was going to see friends in Boston next weekend so it would have to be the weekend after – which was fine by me, I’d finally have a weekend off from dating!

She then stood very close to me, looking straight up into my eyes smiling, I hugged her and went for the kiss but she turned slightly and I got the top/side of her lips.


I figured it was just a screw up and drove off dreaming about our fun-park date in 2 weeks.

On Monday morning I sent her a text asking how the food and flowers were that she had bought at the market – but didn’t get a response all afternoon.  I knew this was a bad sign but she was the one that made plans for a 3rd date.  When I got home from work it really began setting into my gut that something was wrong and I could sense the inevitable “Dear John, Go F*ck yourself” text message – and sure as sh*t it came though about an hour later.

“I loved hanging out with you and thank you so much for taking me to the market, but I just don’t see us as a couple”

I’ve gotten those before, but this time it really hurt.

I shot back in an effort to gain important feedback “I understand, but I’d appreciate it if you could tell me what turned you off for next time”

She replied “No turn off, its just something you feel”

Me: It was very nice hanging out with you, you are a sweet heart, bye”

Her “You’re pretty awesome too”

Me – Select all messages, delete.  Contacts: her name – Delete.


‘Till next time!





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