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I need your advice to see if you see any problems with the situations below, been through something similar, or have word of advice to make it work. At this point, I'm just madly in love and may be blinded by some things. The two things below were once deal breakers for me, and now I removed these two just for him because I rather have a kind man that treats me well than a well off man who treats me like crap.
1. He lives in Hawaii whereas I live in Chicago. I can only travel there maybe the most 2x a year and he can only visit me once a year. This only bothers me obviously because I want to see him in person more. And the last two long distance relationships both cheated on me. I don't want to project that on him, but I am cautious about it. I plan on moving somewhere warmer someday, and Hawaii may be one of those places since I visit it so much. But that's not certain either.
2. I probably make 3x as much as he does. Just guessing since he is a service worker. I own my own home, and love to travel. I actually hid my Instagram because I didn't want him to think I was loaded. I'm not. I just like nice things. And I worked hard on getting my dream home finally. He still lives with his family. I heard that most people in Hawaii still lives with their parents because real estate is obviously really expensive there. The only reason why this bothers me is because most of the men I have dated have always made less than me and were less educated than me. Although, this didn't bother me when I was dating them, it created issues. I realized after the relationships ended that they were insecure, and always putting me down to make themselves better. Or they thought they weren't good enough for me, so they started using a different excuse to break up when I was willing to make it work. After that, I told myself that I would and should find someone who had similar situations, outlooks and goals as me. Otherwise, I'm jealous of his job. It doesn't bother me because he's doing something I'm working hard to be at one day - live in Hawaii, make people happy with a gorgeous view every day BUT work there because I want to, not because I have to.
I met someone recently on a trip and fell madly in love with him.
Ah so let me tell you something right off the bat. You're not in love with him, you're infatuated with him. Call it whatever you want, but this feeling is not love. Love is stable, takes time to develop, and you don't immediately begin loving someone just because you met on a trip or something like that.
Let me tell you something else, from personal experience. Sometimes when we're in a particularly weird/different/transitory state in our lives, we're liable to fall for someone hard if we're looking. You were on vacation, probably in a different head space, and all these circumstances might make the moments you with him unique. But once you move in together, reality sets in, you might realize how much of an illusion all of that was. Just saying, because something similar happened to me decades ago
So no matter what your heart is telling you now, you need to slow down a little bit. Right away, the fact you can only go out to Hawaii two times a year is a big red flag this will never work. But if you make so much more than him and he lives with his parents, and he's in the service gig, he can easily move in with you in Chicago and find another job. Honestly, that will tell you right then and there if he's into you like you're into him. Sacrificing beautiful Hawaii and his family to live in...... Chicago
I think this is doomed mostly because of the long distance. It doesn't help that he's living with parents but depends on age somewhat. Now, is he a saver or a spender? You don't need to be making similar incomes, but you do need to have the same attitude towards money. I think you need to get real about the distance and it's not realistic to expect him to not seek other companionship and have a normal sex life.
It may or may not be real. If you care enough to find out if it is real or not, then you need to take a few weeks off, and spend a few weeks with him, and get to know him to some extent. Then, if you both still want it to be real, then one moves to be near the other. At some point, hopefully, you will both know that it is real or it is not.
If you can't find a way to do the several weeks together, e.g., if your job or his job is more important, then it is not real, and time to move on.
If it were me, I wouldn't even start this process without a mutual agreement to be exclusive ( provisional short-term commitment ), at least until you both know if it is real or not. If it proves to be real, then it becomes a long-term commitment.
Of course we are all projecting our own values on this, so it might be different for you.
Please read your other threads. It looks like you are in your 40s, fairly recently divorced and some friendships fell apart. Now you are head over heels falling for a service worker. Tourist and waiter gemerally does not last far past the vacation.
If you move to Hawaii that "dream house" of yours will likely turn into a 1 bedroom condo in an iffy part of town. It's one of, if not the most expensive places to live in/around the U.S. Couple that with potentially dating/marrying a bartender who makes little money.....meh, you can do better.
This is a vacation romance, nothing more. If this guy feels the same way about you, he will make the effort to visit. If he’s attractive, he probably has several local women he likes already. There’s no reason for him to leave because he has everything he wants close to home. Your moving to Hawaii would only cause problems for everyone.
Since you’re an educated woman with a job and a home, you should be dating men who are at your level who live the same lifestyle you do. Find a guy who travels, for gosh sakes.
Don’t waste your emotional energy on a beach bum. You’ll get bored with him quickly.
How many people have gone on vacation and fallen in love with the cute bartender, and in Hawaii, the fall in love paradise?
If he's the slightest bit attractive women will flirt with him and he can take his pick at the end of the night. If he's attractive and sweet, even more so.
Sure, stay in touch but realize life goes on.
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And I worked hard on getting my dream home finally. He still lives with his family. I heard that most people in Hawaii still lives with their parents because real estate is obviously really expensive there. The only reason why this bothers me is because most of the men I have dated have always made less than me and were less educated than me. Although, this didn't bother me when I was dating them, it created issues. I realized after the relationships ended that they were insecure, and always putting me down to make themselves better. Or they thought they weren't good enough for me, so they started using a different excuse to break up when I was willing to make it work. After that, I told myself that I would and should find someone who had similar situations, outlooks and goals as me. Otherwise, I'm jealous of his job. It doesn't bother me because he's doing something I'm working hard to be at one day - live in Hawaii, make people happy with a gorgeous view every day BUT work there because I want to, not because I have to.
