I let him back in and now I am kicking myself #2

I am getting to the bottom of these questions. He does manage a couple of private properties, he said. I am not sure why he quit his job of 20 years - I will casually ask him. I believe his cousin is compensating him for helping move the boat from one country to another. Everything he is doing to help others, he is being compensated for. Yes, no job and no job stability IS a bit concerning.

I agree - the last thing I need is disappointment and heartache. I am backing up now emotionally and am being far more cautious about him. I am not sure how to approach the conversation about monogamy.....

Approach it directly. Like everything else. Next time he says he’s sleeping over, say hey since we are doing XYZ when you sleep over, for both of our safety id like to discuss if we have other partners.

As about other stuff , how is he paying child support? One can’t be without stable full time job if they have to pay child support. Is he not paying in full? Accumulating arrears? Id not ask that directly, perhaps it’s intrusive, but you could ask how often he sees his child? That’s legit question.

Simply making ends meet when you are on your own and have no obligations, maybe, free-styling and maybe not needing much could be ok. Not with 11 year old!

He pays alimony, lives on a lake in NY with low rent and seems able to meet his expenses. He sees his child as often as he can and talked about flying his child up to visit him in NY soon.

I can ask him about safety regarding sex.

There is nothing wrong with taking precaution when dating.

So glad you are being careful.

So... he told me this morning without my having to ask that he is not and will not go sleep with someone else. So that's good. And, he said right now he's kind of just winging it in life. I asked him last night how serious he is about moving to the Caribbean. He said it's something he's dreamed about for a while, wanting to be a boat captain, and that he's not totally dead set on it. Yes, I am still being cautious with my heart, but I had a really good time with him.

He makes me happy.. he makes me smile. I’m enjoying this.

I saw the new guy again last night and it was a bit strange.

We went to see music and drove there separately. When I arrived, he stood miles apart from me in the music venue, seemingly wanting space from me. I thought it was very odd given he had just spent the night with me, so I stayed away a lot of time, but would go to his side to dance near him from time to time. But Jay (that';s his name) continued to keep his distance.

Finally, I asked his buddy what was up... I asked him if Jay wanted space from me and if he liked me. His friend asked me what I am looking for, and I said well, I don't know, but I don't want a fling.... his buddy then tells me that Jay is not a player, that he is not looking for a fling either, that he DOES like me and wants to hang out with me.... that he doesn't want space from me and wants me to hang out with him...

After a while, I was a little tipsy from a few drinks and asked Jay to come home with me, despite me having a 15-minute interview in the AM. Jay opted to drive back to his home in New York and not spend the night. He told me he's trying to do the adult thing, which is to allow me proper prep time for my interview. He did kiss me goodbye and sent me a text when he arrived home.

I don't know what's wrong with me. I want to take things at a faster pace, and am impatient. I know I need to slow myself down and really get to know this guy's character, but when I really like a guy and when I get excited like I am now, I go all in instead of hanging back, taking my time.... I've always been this way and need to change. I already get butterflies when thinking of Jay, and I really enjoy his company. I'm gonna have to take things at his pace and I am not used to that...

Change is HARD.

Why not ask him why he is standing far away from you. It seems like you thought you going to the event together, just driving separately, but he didn’t see it that way? I’d not be asking his friend if he likes you. Speak to him directly. He’d provide some insight, maybe. Maybe he thought you were standing too far yourself?

I’d start proposing events doing things like going on a date half way on a neutral territory or attending things together rather than inviting him to sleep over. Have you even been on a date with him? Not a sleep over and not seeing him at the concert with others there, but just two of you meeting up and hanging out, not at home. It doesn’t have to be expensive. Coffee shop and walk in a park or a museum trip when it’s a free day, cheap matinees movie etc. No inviting him over. No sleeping at your house. You’ll know pretty soon what’s up. That’s usually a very good litmus test where it’s all going.

I hope you didn’t drive home under influence.

Well, when I had texted him earlier in the afternoon, asking him to spend the night Friday night (because we're driving to a show Friday together), he didn't reply at all. So, when I first saw him last night, I asked why he didn't reply, and at one point in the conversation, he told me he didn't know how to respond to me and then told me he hopes I didn't feel uncomfortable. Maybe I was too forthcoming about wanting an answer by text from him, or too confrontational about not getting back to me. He has always replied to every text I've sent.

I already did approach his friend about it, so that's said and done. After I had spoken with his friend about him, his friend must have said something to him because Jay suddenly started to give me far more attention and was coming up to be next to me, or began dancing next to me, while also touching my back affectionately. So, perhaps my talking to his friend became a positive thing...

I can offer that, but I don't right now want to spend gas money traveling to meet halfway.... we're seeing each other tomorrow eve for another show and we'll be driving together along with his buddy this time.

No, I was fine by the time I drove home. I was drinking water at the end of the night.

Wow, the angst involved in dating again after an abusive marriage. Little did I know! Jay called this morning and everything is good. I feel much better.

I get not wanting to spend money on driving. Then when he drives to your area, maybe you two can do some dating in your area. I don’t know, it’s just a good indication of man’s interest if he actually wants to do more than sleeping together or have you riding along with his buddies. I’d be a bit apprehensive that when it’s not bedroom activity it’s always with other people (and he’s not even acts as you two are there together) and the only time it’s two of you it involves sleeping together. Not saying he has some less than honorable intentions, but is he actually dating you?

It's only been a couple weeks so far, so I don't know what to call it. His friend told me that Jay is not a player and doesn't just want a fling, so there's that to factor in, which I would say is very positive. Jay does not come across as someone just wanting sex. But we live apart, and it's easiest if he visits me and spends the night. Plus, I am enjoying that, so what's wrong with spending the night?

We did go out to dinner the other night, and the other time he visited we ate out as well. We also talk a lot about a lot of different things, when he does visit. It's substantive conversation.

There is nothing wrong with anything you are doing. It’s just because you are questioning where it’s all going and seem unsettled about some of his behaviors, I thought there are ways to make some adjustments. Like you asked him to sleep over on Friday, then you also asked him to sleep over last night. My thoughts were that if you stop asking for him to come spend the night, how is he going to proceed and initiate interactions. But that was just the thought. Of course there’s nothing wrong with anything. There are no rules

I'm laying low now and will wait for him to initiate asking me when he can see me again. I am not going to extend any additional invites and will let him take the lead next time.

I think it’s a wise move. Hugs

Thank you.

I now have a second interview next Tue with the law firm!!! I am sooo thrilled! On top of that, I had told the full truth about what happened in my last job to the HR Director, and that must have been acceptable since I made it past round 1 of interviews!!! YAY!

Great! Fingers crossed for next Tuesday. I believe it’s always better to tell the truth. They probably appreciated that you were up front. Very nice.