I agree that by posting this here, you kind of answered your own question. If you're feeling so much doubt, then it's probably not for the best.

I see 2 things that would concern me.

All the texting and phone calls and such could be a control freak thing that hasn't reared it's ugly head yet.

Taking you over seas away from family and friends. To what country? You most likely won't immediately have a job, so no money, so if it goes wrong, how are you going to leave? Also what about domestic issues in the country? Is it a woman friendly country? Or,,,,,,,,? Not so much.

That little voice in the back of your head, that is saying this is not a good idea! Listen to it. You might not be able, at this point in time to identify exactly why you feel this way, but trust me the voice is right!

If it's possible, I know it may not be, I'd speak to his ex's. Why did things go south in those relationships?

Thanks for the advice. I must admit, deep down, I know I was looking for the "end it!" answers to justify that I was feeling this way.

And so my next question is....how should I end it? I don't want to hurt him. In fact, ideally I'd like to stay friends.

I wouldn't bother - a man in his 40s who is twice divorced with kids and an evolving career, likely has no time to stay friends with a 23 year old girl who isn't romantically interested.

A lot of girls try and "be friends" to not seem like a bad guy or to let a man down gently but men are quite the opposite - just tell him it's not the right match and move on. There are very few women around his age/stage in life that will be interested in him if he is still "buddy" with his 23 year old ex girlfriend (speaking from someone who is more at his stage in life).

Just be honest, there's no how to. Tell him your concerns and that you've decided it's best to move on and you wish him well.

I can't say what you should do for sure...but I will just say what I wish I would have told myself 6 years ago in regards to certain men that were in my life...TRUST YOUR INSTINCTS...You seem to have several well thought out considerations.
I also think BerryBlonde has an excellent point...age gaps are no biggie in "just for fun" relationships...but how might you feel at 43 when he is almost 70, particularly if you start a family.

Don't bother trying to stay friends. You might stay "friendly" but trying to stay friends with an ex is generally something that takes a cooling off period first. You both need to move on. The kindest way to end it is to just make a clean break, be honest but not cruel, and then avoid calling/texting/emailing or other contact for a considerable period of time (minimum 6 months). Otherwise you risk the make up/break up cycle. It's not healthy. And like someone else said, the odds of a 40-something year old man wanting to just "be friends" with a 20-something year old woman is unlikely.

Just tell him the truth, be very direct. If you end up being friends that's fine but sounds like he's kinda clingy so "being friends" to him might just mean "I've still got a chance with her".

I find guys are only agreeable to being friends in the first little bit, when they think they still have a chance with you. Once they finally realize they don't have any chance, you don't hear from them again!

When I was younger I tended to date "older men." My sister, who is quite a bit older, told me "Just remember, when you are still ready to kick up your heels, he will be ready to put up his feet." Just food for thought....

I'm way biased. But I say end it.

My husband is 20 years my senior. For the first few years, that wasn't really a big deal. These days (got together at 18 & 38) I feel like I live with an old man. I just turned 27. It sucks. There is no other way to put it. We just aren't in the same stage of life, or anywhere near it. He has health problems, and he's tired all the time. Our kids are young - 6 and 1.5 - and I get so mad at myself for picking a man that won't likely live to see them become adults.

Originally Posted by L J:
I'm way biased. But I say end it.

My husband is 20 years my senior. For the first few years, that wasn't really a big deal. These days (got together at 18 & 38) I feel like I live with an old man. I just turned 27. It sucks. There is no other way to put it. We just aren't in the same stage of life, or anywhere near it. He has health problems, and he's tired all the time. Our kids are young - 6 and 1.5 - and I get so mad at myself for picking a man that won't likely live to see them become adults.

Laura :hug:

This may be unsolicited, but my mom told me not to marry an old man. Are you okay? I remember seeing some earlier posts about you being uncertain about your future with your hubby. -- Even though, divorce is always devastating, but if you are unhappy....

It really does not matter, if he is older or younger or rich or poor or whatever, if you are not getting good vibes! DO NOT DO IT!

The little voices in the back of your head are there for a reason.

Trust yourself. Always.

Plus, the age difference can be tricky. When you meet his friends and they have kids close to your age... Happened to me, true story. It was weird.