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

I think I will talk to him about it before making up my mind. I want to find out how serious he is about moving. And, if I really like a guy and he is able to pull his own weight financially without borrowing from ME, then it's fine by me whatever he does to make money and earn a living.

Ok, my best girlfriend says I should not mention anything to him... to just have fun right now and see how it goes. I don't know what to do now... I don't want to start to have feelings for someone who may move out of the country! But I also don't want to scare him away by bringing it up too soon, and too early into things before we really know what this is....

Either way is fine, just beware. The last thing you need is another anchor.

You know yourself better.

If you think you can just have short term fun and then move on, then it’s all good. But I’d say if you already want to talk to him more, then maybe it’s not that simple. We are at age when we know what works for us. “Have fun and see where it goes” never really worked for me. I am either in or I am out. I have no time for other stuff. And if I am just lonely or bored or want a companion, then it doesn’t need to be a man. Social hobby groups and girlfriends is a better fit for me.

If casual dating is something that suits you, then why not. I think you should do what feels authentic. But don’t date him out of boredom and loneliness. It never works

If you end up getting hurt, then you’d need a new guy to help with the hurt from this guy. It’s never ending cycles then. But these are all just speculations. You know what works for you

I don't think I can just have short-term "fun". I want something more substantial and longer-term. I've gotta figure out when to talk to him about it.

Can you have a casual conversation about his plan to move? The next time he mentions moving to the Caribbean, be curious and ask how long that's been a dream. A serious conversation may spook him, but a conversation on a getting to know you level may help you get a bit more info without revealing your level of interest.

There's a difference between wanting to do something and actually doing things to make it happen. It sounds like youneed to ask a few questions to find out if he's dreaming or actually planning and doing. You don't need to reveal any of your feelings or fears to show an interest in something he's mentioned a few times.

I understand how you feel.

I think you might spook someone if you tell him you plan on him proposing by Christmas lol Asking if he for real plans to move out of the country is a legit question. I also hope you discussed exclusivity if you are already intimate. If not, I’d ask directly. I’d not just assume. In general it’s just fine to ask direct questions. If someone gets spooked, well maybe it’s for the best then. What are they hiding if they are afraid of questions? If someone asked me what my plans are, I’d not get spooked.

To be honest I'm seeing some red flags when you talk about this guy. He manages properties (how? does he work for a management company?) but also needs to do odd jobs and drive puppies to their new owners to make extra money? He's available for texting during the day? He's talking about relocating his cousin's sailboat and talking about moving to the Caribbean? He sounds like a smooth operator. Just because he appears to have a lavish lifestyle doesn't mean he is actually well off or even financially secure. I hope I'm wrong but I would be SO careful with this guy.

Good suggestion. I think I could also ask him if he's very serious about moving to the Caribbean? Like, how serious are you about moving?

We have not discussed exclusivity, but I am safe and use precautions. I don't believe in exclusivity this soon... I think it's too much too soon kind of thing.

He doesn't come across at all to me like a smooth operator. I think he's in a transitional spot in life himself. He quit his property management job of 20 years 1 year ago. So, he's doing his own thing now to make ends meet, which yes, could be a red flag, I suppose. I don't think he's financially well off, but he's making ends meet and is doing what is necessary to do so.

I will be careful... I am definitely cautious....

I agree with Samicat. At 49 when asked what he does for a living, I’d expect a specific answer I am a welder working for XYZ company that makes ornate gates or , I am a property manager in XYZ company that manages condominiums. Vague answers like what property he manages (his? Someone else’s? Manages how? He doesn’t actually have a job?) and odd random jobs at 49 are strange. Driving puppies?

It might not be as much about money as it’s about unstable life style at his age. He’s going to sail for 10 days? He has ten days vacations from work? It kind of points out that perhaps he has no full time job. So no health insurance then either?

I’d google him and see what pops up. You’d be surprised what you can find by simple internet search. I once had a bad feeling about a man and oh the stuff I found. I couldn’t even believe you can find stuff like that by simply typing a name.

I didn’t see your reply before I typed mine. It’s perfectly fine not to be financially off. Just lack of stability approaching 50 is concerning. One doesn’t need to be rich. So he doesn’t have a job. For the entire year? He quit his job and can’t find another for the entire year? Why did he quit and why isn’t he getting another job? How is he affording all these things he does like skiing and sailing, those are expensive activities.

I don’t believe in exclusivity after few dates either. If I intend to sleep together then it’s a bit different though. If I feel it’s too soon to ask if he sleeps with other people, then it’s too much too soon for me to be intimate. People ask these questions all the time. Don’t be afraid to ask questions and spook a man. If he is the right man, he’d not be scared but in fact would welcome frank conversation

Good luck. It might all work out really well. It’s just the last thing you need another disappointment and heartache from a man

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.