Date 10: When It All Goes South

I was super excited about Tommy.

That should have been the red flag from the start: dating requires you to proceed with caution, and if I get giddy, chances are it means “Danger, Will Robinson!”

Tommy looked like a great match and had a lovely profile.  I wrote first, which I normally don’t do, but he replied immediately.  Conversation started easily enough and then stalled for a few days.  But, he came back.  I never asked why and we just started up again.

He asked me out quickly and we had fun making plans together.  He knew some of the best little hideaways in the city and had some great suggestions.

I was excited because we had the fun, easy banter that sort of goes sexual, but never turns dirty, just enough to make you a tiny bit tingly.  Plus, he said he was excited, which is, in itself, so much fun to hear.

He arrived to the bar before I did and I was a little disappointed with his looks.  Hard to explain, but he looks like his photos and then not.  He was 6′ tall, but appeared smaller.  He was rock solid and cut, a beautiful physique.  Super smart and savvy too.  He was born and bred in this city so most natives tend to have a bit different world view than the rest of us, again, can’t really explain unless you live here and experience it.  He was from a particular area I tend to avoid matching with because of its heavy accent, but he didn’t have it (always found that weird too because some people have that accent so strongly it’s annoying to listen to and others from the same city don’t).

The thing about city boys is attitude, and many of them have it, it’s just the way it is in this city.  When I was young it really attracted me to them, the bad boys.  As I have grown older, some of the qualities make me want to run and hide.  Of course, everyone is different and it takes time to know someone….but my experience has been very consistent.   Stereo-types exist for a reason.  I use some of them for my dating criteria as I mentioned in a previous post, but I try not to allow them to fog my view upon meeting a person.

Sadly, once again, the stereo-type was right.

We had fun at the first bar, but he kept pushing me to tell him what I thought about him because he knew height was important to me.  I guess I didn’t respond with enough confidence and he got around to insisting he was taller then me even in my heels.  Then he made us both stand up in the small bar, go back to back, and loudly asked the room to determine who was taller.

I was.

He still insisted it wasn’t possible unless my heels were 5″ and not 4″

The next few cocktails went down to fast.  I knew this was time to stop, but I was almost weirdly curious about when we were going to hit a wall.   I can’t even recall all the red flags that came up in his conversation.  I know one of them was that he had no male friends and only female friends.  Another was his anger over losing his friends on 9/11 and wanting to kill and entire nationality and how he overcame that in the form of tripping on E at a U2 concert (Thank goodness for Bono’s wide words?!)  Another was how he kept telling me how sexy I was, how much more beautiful in person I was and how he hand’t had sex in a very long time.

We finally kissed.  He was a perfect kissing partner, and I also knew the chances of that were quite high.  His hand went right to the back of my head and he laced his fingers through my hair as he pulled me hard forward.  I honestly couldn’t stop kissing him.  He was luscious and his back, arms and shoulders rippled with every move.

I could feel the alcohol coursing through my veins.  I don’t often drink cocktails and they work on me much more quickly than my oft selected Prosecco.

We chose to leave the first bar and head to another where his friend was a bartender.  Before that, though, I stopped in the bathroom.  It was a single bathroom so I entered and locked door and did my business.  When I opened the door to exit, Tommy was right there and pushed me back in.  “Don’t you want to see what you’re getting?” he said as he started to unzip his pants.  I pushed him away and said “No, thanks, that’s just gross” and left.

I should have left him then.  My mistake.

We hopped in a taxi and made our way to the second bar.  We made out like mad in the back seat and I eventually realized he had unzipped his pants and was masturbating.

There wasn’t much to masturbate, so if I wasn’t convinced before, this size queen had her ultimate decision handed to her (yes, pun intended!)

This is my own fault.  I was hungry, I wanted to eat and I was a bit tipsy.

The second bar was even more cool than the first.  We met his girl friend the bartender and ordered another drink.  He left me his credit card and walked away to the bathroom.  He was gone a while before I looked over my shoulder and realized he had met someone (I don’t think he knew them) and stopped to speak to them.

Then he came back and said he was going outside for a cigarette! WTF?  Smoking is a deal-breaker.

I ordered food on my own and sat a the bar.

Then I text Bennett.  Things just get worse from here on out.

Bored, alone and drunk on a first date, we got into a heated text exchange.  Tommy came back from the cigarette and continued to speak to this couple.  He leaned over to say it was a really important business contact .

For a half hour.

I ate and text Bennett some more.  I also continued to drink.

He brought the couple over to me who said I was lucky to have such a wonderful “boyfriend” (he had previously introduced me as his girlfriend) and they wished us the best of luck, and could tell how much he adored me (again, WTF?)

His bartender friend mentioned to him there was another business associate she wanted him to meet, and he left me again.

I finished eating and stopped texting Bennett.

Finally, Tommy came back and I made mention that it wasn’t, perhaps, cool that he left me twice for so ling.  His answer was “I was doing a big deal, this could be good for US!”

Ok, official creep factor has kicked in.  US?!!

Then my phone started ringing over and over and over.  It was Bennett – worried or angry I hadn’t replied.  Tommy sees this and goes utterly ballistic that I have an x who is a psycho stalker and he wasn’t getting involved with that type of drama.

I got my coat, put it and and told him I was leaving, all while he was literally throwing a fit about my phone ringing while I was on a date.

I couldn’t escape fast enough.

While in the car home, my phone started to chime with text, one after the other.  His text read “Calling a girl 50 times in a row (he called 3) is not cool while on a date.  That dude is cray cray.  Wouldn’t you freak out if I had a girl call me that many times in a row? I don’t judge you.  It’s not your fault your so goddamn sexy.”

Block.  Delete.  Move on.





Author: Madeline Harper

My journey through divorce and an emotional and sexual reawakening. Love, laughter, friendships, family and heartbreak included. And there is sex, lots of it, so close your eyes and turn the page if that's not for you! While I started this blog as an endeavor to journal my thoughts and feelings in an attempt to better understand myself, it has become an amazing platform from which I have met some of the most interesting and wonderful people in my life. My path is often crooked, but I hope you will share in the journey with me.

8 thoughts on “Date 10: When It All Goes South”

  1. Ohhh UGH! And so it was just okay for him to leave you sitting a few times alone, but the minute your own phone rings he goes nuts? Weird!! And a deluxe red flag! May your next prospect/date go much better.
    But I hope you don’t allow Bennet to wrangle his way back into your life.


  2. The lesson from this date: when the guy corners you in the bathroom, go straight home…ALONE. Jacking off in the cab was somewhat juvenile. The whole Bar 2 scene was ridiculous. Good job on getting yourself out of there. NEXT!!!

    Liked by 3 people

  3. I literally started laughing at him masturbating in the taxi. For reals? Does the man have no decency? It’s one thing if you two were hot and heavy in HIS car- by a taxi? Geez…this date was a cacophony of errors. So sorry M.

    Next please!

    Liked by 2 people

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