My Three Girlfriends, Part 1

October 12-14, 2017

I was doing business down in Philadelphia, and I was a two-timing man these days.  Two girls in the flesh and one in the abstract.  So, to recap, there’s Litaly, there’s Guidish, and there’s Cape Cod.  However, if you remember, I started to fade Litaly after a recent dating faux pas of hers:


That wasn’t the only dating faux pas of Litaly’s that night, as she apparently went for the grand slam right afterwards:

And if my boner wasn’t already wilting, why not just top off the chocolate fruits and fishing statement weirdness with a huge wtf:

Not really sure my girlfriend #1 isn’t more trouble than she’s worth.  But, I consider all of this a speedbump along the journey of David Shepard 3.0, so no need to stop:

So, while Litaly is still on the roster, her fade provides both the impetus and opportunity to fill her space with another warm body.  Plus, girlfriend #2, Guidish, is similarly low maintenance.  I thought I had another girl, but couldn’t seem to find the room to squeeze her in.

It should be noted that this juggling was only made possible by the specific logistics of this situation—that is, my harem stays in line:

I actually spend the most amount of time communicating with girlfriend #3, Cape Cod; she of the 250 miles away, and she who I have never met.  Guidish and Cape Cod also happen to have the same exact name.  Because, when three-timing, you need not waste precious cognitive resources on remembering a silly little thing like someone’s name:

10/13/2017, 7:53pm: Text to Cape Cod:

10/13/2017, 7:54 PM: Text to Guidish:

Two birds, one text.

And Guidish knows the deal:

And, unlike the old adage, I can still have my cake and eat it too.  With Litaly, the less I pay attention, the more she craves.  It’s simply human nature:

Ditto Guidish:

If you have ever wondered how exactly how to pull off two-timing and then some, I have a very simple game plan:

1) Stop believing in Disney Monogamy;

2) Don’t place too much importance on any one individual;

3) Be up front about your level of commitment:

4) If you stop to care, it might actually be bad if the girls know one another;

5) Don’t fret over how to end it…or fret over any of it:

But, does David Shepard have a conscience?  No.  There are no rules or fairness police to the rescue here.  And, I’m no stranger to the shoe being on the other foot.  I consider it necessary self-learning and character development along the journey:

The way that this is going, I have a feeling that Litaly’s time for self-learning is approaching quickly.


I’m a divorced dude living and dating in New Jersey. This blog is my story told through a first-person view of my text messages to my friends and/about my dates.