dating Jack

Starting to settle in: dating Jack

The conversations with Jack are starting to meld together. It’s the problem when living my life outpaces my ability to write about it. I’m going to try to get caught up with this post with our dating status.

We had the kind of fourth date made necessary by single parentdom: a late night visit. It was a three-act play similar to the third date: a drink on my couch with lots of conversation, moving to my bedroom for some good sex, and then talking far too late into the wee hours of the morning.

This time, instead of waiting for me to suggest it, he asked to take me upstairs. I liked it.  Continue reading

From theory to practice with Leo.

Leo and I booked a date after our big talk. A full-on dinner and activity weekend date. I was cautiously optimistic.

It was going to be a beautiful day so at the last minute we modified our plans. He came to my house just after lunch and we planned to do a day trip to a nearby wine region, visit some of the quaint towns in the area, and have dinner. If anything was going to be an issue, it wasn’t going to be our itinerary!

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Two steps forward and one step back.

Previous Post

I had some decisions to make. Did I believe him? Mostly. I knew there was a chance he was telling me what he thought I wanted to hear, but seeing how uncomfortable he was, and the way he told me, led me to believe there was far more truth to his words than lies.

I didn’t write it all out, but I did challenge him on a number of things during our conversation. The most important for me was how it was possible he didn’t feel comfortable with me, given how open I’d been with him about my own sexuality.

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Leo laid bare.

Apparently some of you aren’t happy even when I skip to the end of my story. So from now on, you’ll get what you get 🙂


Leo paced back and forth between my living room and kitchen while he spoke. He was clearly uncomfortable. He drank water constantly.

He started with a statement about how he was raised to be the one who was strong and couldn’t be vulnerable. I wasn’t sure where he was going, but it was just the intro. Continue reading

When is a relationship over? And why do I have to think about all this sh*t again?

I had a post in draft format prior to my date with Tony on Wednesday. It thanked everyone for their great advice and laid out a plan of what I was going to address (the ED) and how I was thinking about the other discussion I wanted to have.

At one point I said:

And the whole choice verses default thing I’m struggling with so much right now? 

I can’t push for an answer. He’s told me what he can. Which is he doesn’t want to date others, he likes what we have going, and he thinks we are doing well. His actions reinforce this. I know he likes me. Do I want to know more? Yes. Will he have an answer different from a few weeks ago? Probably not.

My core dilemma is this: 

How do I not let him “set the pace of everything” as one in my sisterhood wrote recently? How do I find the balance between chilling the hell out and being true to my actual needs and wants? When is talking myself out of those needs too much?

How do I make sure I don’t make the same mistakes again? 

There is no easy answer. No script. Even if I script my actions and words, I don’t know Tony’s.

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Well, that was unexpected:  Tony has a big reveal.

I took Tony to his first symphony last night. With a meeting cancelled at the last minute, I met him early at a local pub to watch a sporting event. He’d never seen me in work wear before and when I strolled in with skirt suit and 3.5″ heels, he commented on how good I looked.  As usual he smelled amazing and gave me the best appreciative looks and I soaked it all in. I was only one of two women patrons in the entire bar.

We watched the game and he taught me some rules and we had a couple of drinks and in between plays we chatted. He thinks I’m good luck for his team and I teased appropriately for this opinion (of course I also joked that two years now he would be saying “omg she drives me insane but she’s good for the team”).

The guy sitting next to us at the bar looked like a corporate version of Ariel. It was disconcerting and I had to look really closely to make sure it wasn’t him. He so pathetically flirted with the female bartender when he sat down, but that’s a whole other post. Continue reading

Decisions, decisions.

I don’t like this part of the play. It’s  better than being in a miserable marriage that is on Act IV. But still.

There is no playbook. Nobody to tell me if I do X then Y will happen. So often we try to control another person. The only thing I truly control in this life is my own actions. Or reactions.

I’ve been patient. Paced myself – which was the right thing to do, no question in my mind. I have not pushed like I would have before.

I am still unsure whether he is real long term relationship material. Frankly, that’s irrelevant. I don’t need to know that and my cynical and realistic brain knows that there are things you simply cannot know about a person until some time has passed. Continue reading