About 8 months ago…
All this flirting with Chi-guy was beginning to show some promise. I had finally made up my mind on the sex question and the answer was Yes! I was definitely excited by the thought of getting physical with him, and I was beginning to think that he might actually be ready to go there, too.
Thus, my texts, emails and conversations with him, while entirely genuine and from my heart, were definitely directional in nature. I wanted to feel confident, when I next traveled to Chicago, that we were on the same page. I was leading the conversation, looking for proof positive that he was thinking the same thing.
Meanwhile, the work I was doing this trip would require a day of running around, doing errands. I asked Chi-guy to spend the day with me; I needed a local with a car to assist, I argued. He would be compensated, and it would be a win-win, costing less than the car rental, parking and lost time if I were doing it all myself. I would take him out that night — off the clock, of course — to celebrate his upcoming birthday over dinner. He agreed.
I made flight arrangements, thinking ahead to fly in early Friday and fly out mid-day Monday, so that I (we) would have the opportunity sleep in that final morning.
Things were going well. I was feeling confident. He texted things like: “Good morning, Goddess. What are you up to?”
And I: “Oh, the usual Goddess stuff…listening to a little Kate Bush, dancing in the kitchen, saving the world, etc…”
We had even exchanged some suggestive (though less risqué than prime time television) photos, which is how I know the specific brand of boxer briefs he wears.
The week before my trip, I took a road-trip with my children. As we drove through the countryside, I saw an exit sign for a town with Chi-guy’s last name on it. I texted him a photo.
He shot back: “Oh, yeah, I’m also the Mayor there in my spare time.”
I texted: “Well, your Honor, what do I have to do to get into your CKs?”
Him: “Nothing. You don’t even have to say ‘please.'”
Even writing about it today, I can feel the joy flood through my body. I was immediately relaxed, happy and confident that things were going my way. As a matter of fact, when my girlfriends asked about my prospects in Chicago, I smiled coyly and used the words “locked and loaded.”
The few days before my trip, I coasted on this confident knowing. Chi-guy was silent. Finally, two days before I flew, I texted him: “SO EXCITED to see you this Friday!”
He texted: “Oh, sorry, change of plans. Can’t make it.”
After an initial moment of shock, I thought it must be a joke…still, I couldn’t be sure. I didn’t know him that well…
Him: “Just kidding. Looking forward to seeing you, too.”
This is what I call douchebag humor. Douchebag humor is when a man has a perfectly decent opportunity to pay an amazing compliment and, instead, chooses to try to be funny because it’s more satisfying to his own ego. In other words, if you are the woman on the receiving end of douchebag humor, you know how un-funny it is!
And, even though he had paid me a half-assed compliment in the end, “looking forward to seeing you” was stiff and formal compared to my “SO EXCITED” gushiness. He was running hot and cold, sending mixed messages…something was going on with him…
I decided to stay positive. After all, what single guy — after more than a decade of married sex — would turn down the opportunity to go to bed with a long-time crush?!