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. 

The sex was better. He went down on me and it was divine. We still don’t have the right angles all sorted for regular orgasms, but I have faith. He was more comfortably aggressive this time, and I liked that too. But he had some hydraulics issues, losing his erection a few times (but it would come back). I wasn’t too fussed in the moment but later did wonder what contributed to it.

We lay in my bed for a long time after sex, talking about anything and everything. He disclosed things about the breakdown of his marriage and last relationship. I told him about Tony. I learned he doesn’t like to hear stories about past sexual experience. While I get it at some level, inwardly I cringed since I’m pretty open about things, and of course I got to thinking about the blog.

In the days that followed, he texted me about the ED issues, saying:

I realized what happened the other night with my physical troubles. I’m so happy to have an intelligent conversation with you and be attracted to you that I wasn’t finished with the first part and I moved us to the second part. If that makes any sense.

Not sure I follow.

I get both with you. Intelligent conversation that I can relate to and share similar interests, as well I have a physical attraction to you. In my prior situation it was mostly physical so having both with you is an incredible bonus to me. But because I haven’t had a normal conversation with a “normal” woman in so long I really enjoy that part. Normal meaning someone who is logical, savvy about the world, and isn’t incredibly flighty. Huge turn on and makes things last.

Okay, I’m following you.

As in, I don’t just want to fuck you and leave. I want to be challenged have a real conversation about the world fuck you and not leave.

I held my phone in my hands with a huge smile. Perhaps not the most romantically phrased statement, but it spoke to my most inner relationship desire: find a man who wants to fuck me, make love to me, and talk to me forever.

I’ve seen him four times in total. We’ve spoken on the phone most days. He has his kids two weeknights a week, and every other weekend. Thank goodness our child-free weekends are aligned. He doesn’t seem to be attached to his phone when he has them (a positive) which means his texting is erratic sometimes (a negative).

But I remind myself he’s got a parent in the hospital and he’s moving, so things are likely more chaotic than usual. He tells me he’s usually very consistent, so I’m not worried about it.

When I told him it would be helpful for me if we could plan a few dates a week or two in advance, as I often book things with friends and family, he said “get out your calendar”. We booked two dates for next week and another one a couple of weeks out for a big sporting event.

On the weekend, we had a late night conversation each night. Meaning on Friday night, drunk after an evening with girlfriends, he called me and for two hours I (mostly) blathered on about things such as why he didn’t keep his eyes open more during sex and how vulnerable I felt being exclusive with him (things he took completely in stride, it would seem) and didn’t hang up until 2 am. Saturday night we spoke for another two hours. He mocked me gently for the night before. We didn’t hang up until 1 am.

He’s bad for my sleep.

My Mom asked me if there were any red flags. I can’t see any yet (tell me if I’m being blind!) but a few things are on my radar. The first is actually about his interactions with me during sex. He says he is all about his partner’s pleasure, yet often he’s not watching my face. Perhaps it’s nothing. I know I’m used to Lewis and Tony who get off on my pleasure, so they paid really close attention.

Jack seems different, which isn’t bad or wrong. But I can’t help but wonder whether it means anything. 

But then I also wonder how he ended up in a second long-term relationship with someone seemingly incompatible (other than physically) and why it took so long for him to get out. I guess my fear is he’s not into me as much as he is the idea of me or a relationship…. perhaps he’s the kind of person to not want to be alone (although he was for a year after his split). So he closes his eyes during sex because it’s not about our connection. He’s complimentary via text but not in person because it is not about me.

Please understand, these are not things that are taking up a lot of my time. They are nagging thoughts that occasionally come up. They are my interpretation of things, which are most likely entirely wrong.

I know I will figure it out as I get to know him better. I can’t point to anything concrete that has me actually worried. It’s very early days, I’m taking each day as it comes, I’m enjoying the time we spend together, our discussions, the feeling of having someone be into me. Our next date is tomorrow night.

But I do need more sleep.

15 thoughts on “Starting to settle in: dating Jack

  1. I am wondering whether the hydraulics issues may be why he closed his eyes, trying to focus on that, or not to, depending…

    I close my eyes often during sex, so does The Dancer. It’s because we’re so taken in by the sensations that we can’t focus on the other I guess.
    But then at times, we’ll watch each other and then the world falls into place. Or disappears. Or both. I’m not sure… πŸ˜‰

    My advice would be don’t let these thoughts take up more of your mind than they already do. And if they did grow, then address them with him. He is probably the best person to answer the why question!


  2. I’m πŸ˜€ to see the regular updates. Believe it or not, I have a piece of advice: Don’t rush to judgement on Jack. With the exclusivity you might feel the need to “move on” sooner than normal, allowing other encounters.
    I know you are aware of this, but I wanted to try out my advisors hat🎩.

    • Advice is welcome. I’m fine to have exclusivity with Jack because I feel there is real potential with him and I’m not settling (as in, it’s not like Alan where I knew there wasn’t a strong intellectual connection but I tried anyway). So this way I can experience more and make a decision potentially faster.
      If I get frustrated and unsatisfied and want others then I think it’s a sign he’s not right for me.

  3. I agree with Dawn about why he may have closed his eyes and think you are doing great by not making a big thing out of the ED issue. I think both those concerns will sort their selves out with time and you can have fun while they do πŸ˜‰

  4. He hasn’t asked to marry you and hadn’t used the L word yet. He sees chemistry. I don’t see any red flags, and you seem more hyped about him than you were Leo or Fox. With Leo I feel like you guys would have made excellent friends. He was kind and there when you broke your leg, which made you want to really try, but your initial reaction was nah. You did see red flags with hwsnbn and we have an idea what happened there. Fox, you were trying to like him, fearing you were blinded by the chemistry from Tony. He couldn’t handle the kind of woman you are which I don’t think is an issue for Jack, but he just let’s you know he is the jealous type. He wants exclusivity, (not a bad thing, I’m that way too), he doesn’t want to hear about your exploits, but how will he react to you being platonic friends with men? That could be a red flag. He could be self assured not to worry, but I think it’s something to find out sooner than later, maybe mention going out with a group of friends a male friend included. She if he gets stuck on him. Everything else seems good.

  5. I could well be off-base, but the issue with his former girlfriend calling the police would rate at least a yellow flag in my book. Their breakup may have been bad, but there could well be some anger issues that were called into play at his end. I know that there are almost always two sides to every story, you’ve heard his, and it may well be accurate, but I’d at least be a little concerned about that. You both are still getting to know each other. Like most things, I think the best way to handle it is to take things at a reasonable pace and get to know each other better. Time will tell….

    Who knows what lies behind his ED issue? It could well be that he finds someone like you intimidating (intelligent, successful, sexual–a combination which could intimidate almost any man) which could easily have an impact. Stuff happens in that department so I wouldn’t take that seriously.

    • Hi Bill – yes, I completely agree with you that it’s a yellow flag. It’s one thing to have an argument, another thing entirely to call the police. I know what it took for me to get there with HWSNBN. So yes, I’m keeping an eye out for it.

      And I think you’re on the right track with the ED. I’m not overly concerned and suspect it will resolve as we get more comfortable with each other.

      • If I start to get serious about someone I always run down to the local courthouse and do a check on their criminal history just to be safe – when you have kids you can never be too careful. One domestic call can be written off as a flook if there are numerous ones by numerous women then he has a problem – also never hurts to see if they’ve been involved in other crimes. A background check online is not to expensive either but they only go back 10 years unless you upgrade.

        • I’ve never done a criminal check on someone but I understand why you’d suggest it. One of my friends knows his ex-wife (of course…the same one that knows Tony’s wife) and he’s been vetted through her as well. My spidey sense is not worried at all about violence or criminal issue.s

What do you think?