first date surprise

Finding more things in common with Gregory.

The morning after my first date with Gregory, I was excited. It was a nice change to have had such a great intellectual and physical connection, with a man who seemed to be on the ball and in contrast to some of my recent experiences, well-balanced. Lots of commonalities to explore.

Even my Mom hadn’t seen any red flags in her internet searches.

I told myself to chill out and take Gregory as he comes. Given what I had been experienced with John, I was keenly aware there is reasonable excitement at potential, versus the crazy-town reaction of expecting everything is going to work out. I was determined to not give any impression I was like John. Because I’m not. I had no idea what potential we actually had.

I have to constantly remind myself how others see me. I’m a busy executive and Mom with an active social life who apparently is a real dating catch. Gregory had said enough complimentary things (but not over the top) that I knew he held me in high regard. As well he should, I suppose.

He too is a busy man, with a busy life and presumably, other women have caught on to his dateability. He was traveling that day to visit his children, and I didn’t expect to hear much from him. But I wanted to reach out and say good morning, which I did.

Just before 10 am, I sent him a good morning text and asked whether he liked to sing to music when he drove. I told him to please not text and drive on my account. He replied absolutely he liked to sing but he hadn’t left yet. We texted a little about road trips and car songs and then I said: “I wanted to share… in my 8 am meeting my mind did wander on occasion to you in front of my fridge :)”

He said, “well that’s good to know and trust me, the feeling is mutual.” I smiled as I went into my next meeting.

When I got out of that meeting, I saw he’d sent a few more follow-up texts: “It took me a while to fall asleep and it was not because of the espresso.” And 10 minutes later, “so later tonight will be in the hotel. Going to have dinner with the kids. Give me three questions – no limit – that I can answer then.”

Ooohhh. I liked that. I told him I was sorry for not replying sooner but had been in meetings, and that I too had trouble falling asleep from over-excitement. I told him I was having a party that night with my female friends but would think about questions and send them later.

He said “they can dare you to send certain questions. Lol. Party game.”

“I like the idea of questions, Gregory. I’d welcome a few from you as well.”

“Oh don’t worry, I have a few.”

I was walking to a different building for my next meeting, so said I had a minute while walking and he could feel free to ask anytime.

He wrote: “So I am going to make a prediction. You are very much like me. Fair conservative on the outside. But inside…another story.”

I stopped dead in my tracks in the middle of the busy city sidewalk. Wow.

I typed: “Yep. Busted. How’d you know?”


“Yeah, always prefer honesty, as long as it comes with compassion”

“Just the way you moaned when I grabbed you.”


“You know what you like. Hopefully can intro you to even more.”

My first thought was he didn’t know who he was dealing with.

“I thought you might say you noticed my reaction when you grabbed my hair”

“Yes, that as well”

“I’m walking down the street with a big smile on my face, Gregory”

“Because it is sunny? Lol. Okay, fire the first question”

I knew what I wanted to ask. We hadn’t talked about relationship readiness at all. We hadn’t talked about dating. I had no idea what Gregory actually wanted. I took a deep breath and wrote:

“I’ve been in a meeting so haven’t had time to think, but something I’m curious about is whether you’re open to a relationship at this point?”

“Right person, yes. Not a need, per se. What I won’t do is overly compromise” he said.

“I’m not open to a relationship with the wrong person. Life’s too short” I replied.


He said “I’m glad you asked first. I was going in a different direction.”



“You can go there. I sense you know I’m multi-layered.”

“Yes, layered for sure.”

He said he was about to drive and I told him I looked forward to his questions.

I had a spring in my step the rest of the day and couldn’t stop thinking about him. Could I have actually found my unicorn?

A few hours later I told him I had seven questions so far and would whittle them down. He told me to send him one so I asked him what would constitute a perfect day. He said it was a tough one but I loved his answer, as it would be pretty close to what I would consider perfect as well. Especially the part where he said: “yes, there would be sex (many forms) thrown in all during the day.”

I found myself hoping the sex talk didn’t mean that’s all it would be between us. I’d had plenty of experiences where it was a sign a man didn’t want a relationship, but there were notable exceptions. Would he be one of them?

I asked if he wanted to ask me a question, and he said: “going big to start…craziest thing you have done.”

Oh, crap. I knew my honest answer had to be either the gang bang night or the night with the Dom in the sex club. But could I be honest with this man I’d just met?

I wrote “God. Um. I’ve done bold things in my life but craziest, if I think about that being defined as on the fringes… I’m pacing. Lol. Trying to figure out how honest I can be here.”

He said, ” I’m thick-skinned and non-judgemental, to say the least. You’re allowed to ask back, too.”

I stopped pacing and decided to go for it. “Okay then. I’ve done some things at sex clubs that most people would define as crazy.” I paused with my finger on the “send” button, winced, and pressed it.

What the hell was Gregory going to say? Would he even reply?

Image from the 1949 movie “The Great Sinner”

22 thoughts on “Finding more things in common with Gregory.

  1. I would wait for him to “reach out.” I think part of your problem is exhibiting way too much anxiety when a guy is showing some interest. Be still and allow a guy to pursue you for a change. If they are interested in you, they will. If they aren’t, they won’t. Just a little unsolicited advice.

    • Thanks Oceans. Do you mean anxiety when they are pursuing me, or anxiety when they don’t seem to be? I do know communications gaps are a trigger for me, and I think I do a good job of not letting them see that (I’ve written a post about it actually). You’re quite right that those who are interested will pursue.

  2. oh i recently met someone online and we’re doing the “ask a quesiton in turn” thing now too. I’m meeting him for coffee tomorrow. you’ve been an inspiration.

    i wonder what he would say to your answer.

  3. Ha! I like Gregory. I know you like him too (at least up to this point, and since you may be slightly behind on posting, I’m hoping the joy I feel in your voice is a good indication that the answer you got was rather positive).

    Since you wrote about that question, I thought about it and… the honnest answer that comes to me is marrying my ex. This certainly was the craziest thing I’ve ever done.

    Now, if we get that out of the way… I’ve done a few crazy things, but they don’t really seem crazy to me any more, because they’re so much a part of who I am!


    looking forward to the next post 😛

  4. I would temper the details of your answers with the reality that it does and can affect how men view you i.e. you may not be viewed as relationship material vs being seen as a fun sex toy (for now). Focus on the connection and building that bond.

    Btw- I love Gregory!! And want to see this relationship go far 🙂

    • I agree here. Let him earn that information about you. This sounds old fashioned but I think it’s important to be a bit mysterious in the beginning – focus on your intellectual and emotional connection. The sex is just the icing on the cake!

      • Well, too late for that… I hit send on that text. As I said above, I took the chance because of what he’d said to me earlier that day. I thought it was a risk, but not a huge one.

    • It definitely can affect how men see me. I took the chance because of what he’d said to me earlier that day. I simply had a sense it would be okay… but was still nervous to say it.

  5. You’re doing a great job of not letting on about his response!!
    Keep us in suspense as long as you want….NOT!!!

  6. OMG Ann, I did not know about the sex club and the Dom, did you blog about it? Can I look in your history, dang girl it sounds like we have some similar,shall we say eclectic tastes!!

What do you think?