Trying to see Gregory again.

After I’d heard from him that night, Gregory and I texted back and forth a bit. He was hosting clients for most of the day, including dinner. He said it was exhausting. He was complimentary about my talents when I shared a work-related issue. I told him I was off to bed (I was getting a cold and knew I needed to sleep) and asked him if the next night still worked to get together. He said it did.

The next day arrived. I didn’t text him at all during the day – and at 6:30 he texted saying he hoped I’d had a good day. I replied a half an hour later when I saw his text, and then asked if 9:15 pm would work for him to come over.

No response.

My phone spontaneously died with 20% battery left. I got home from work at 7:30 pm, plugged in my phone and saw there was still no text. I use an iPhone but he doesn’t, so I can’t see whether my text got delivered. I didn’t want to send a follow-up message so thought I’d give it some time.

I hung out with Liam, and when he fell asleep at 9 pm I sent a followup text to perper: “Hey Gregory – my phone spontaneously died tonight at 20% 🙄 – not sure if you got my message?”

He replied “Ann sorry just nodded off on the couch.”

Sigh. He must be tired.

I asked if he wanted to postpone again, and whether we were still on for Friday. When we made plans on the weekend he said Friday should “probably work”, and I decided to be comfortable with the tentative plan for at least a few days.

He said “Yes on for Friday and sorry been going guns a blazing this week never should have sat on couch….true date on Friday. Would like to take you for drinks and dinner if that works with your timing for your coparenting?”

I told him it absolutely did, and that I was free until late morning on Saturday. I added “I will just put my lingerie for tonight back in the drawer then ;)”

“Ann, you’re killing me”

“I’m not sorry. I’m starting to not like your couch”

“You’ll like it when we’re on it”

I liked his style. His flirtation, not over the top but still sassy, made me smile. And in the face of those like John, I just need to keep remembering that his restraint doesn’t necessarily mean he’s not into me.

We were texting about how his couch was good for oral, and in joking about how he figured it out I said “I’m sure experience has dictated it, not that I particularly need to hear about it” to which he replied “I wouldn’t tell you anyway. Lol. But you never know, I may ask you a few things.”

I wasn’t sure what he meant, and he clarified that asking me about past lovers and sexual encounters was one of his kinks. He added that he was being “really open”. I said “why wouldn’t you be, with me? I told you some of my most secret things after just our first date.”

“No reason not to be. I don’t usually lead with it. Some women get freaked out”

“That I can relate to, Gregory. I’m not some women”

“Amen to that”

We had a quick phone call before bed. It was nice to connect with him, however briefly. He said he wasn’t feeling all that well and was going to crash early.

The next morning I sent him a good morning text and wished that he was feeling better. He replied right away and said he was better, and asked how I was. We had a brief exchange, he sent me a text at 9 and I replied a few hours later. He didn’t reply.

Our date was scheduled for the next day and I didn’t know exactly where or when we were meeting. So at 10 pm I sent him a text that said I looked forward to our date the next day, and asked if he could let me know where and when to meet, that would be great.

He replied right away with a location and said “pick a time that best suits you, if that works for you.” I replied saying “I could meet as early as 7?”

It was 10:20 pm and he didn’t reply.

I told myself everything was fine.

The next morning at 9 am, he texted “7 works perfectly. If 730 easier for you that’s fine too. I actually typed that last night and didn’t hit send somehow.”

“7 is good. Fall asleep mid text?”

“No just didn’t hit send. Was setting up a Google home mini in my bedroom. Good sales yesterday and I geeked out.”

I told him about an early morning meeting I had and he said “you have patience and brains and looks. Pretty cool.”

I was off to work. He said he was looking forward to later that night and I replied in kind.

Our second date was 10 hours away.

11 thoughts on “Trying to see Gregory again.

  1. It is uncanny how men do that, fall asleep on the chair or sofa. Seems to be a common thing though.
    Can’t wait to hear about the date!!

  2. I’m not too sure about Gregory. To me the lack of responsiveness seems to be a caution flag. Plus it frustrates me and pisses me off on your behalf.
    What is his future response time going to be later on down the line? Although, I would handle it exactly the way you are doing. Gregory seems so awesome with such potential. I really hope that he is.

What do you think?