Question - What Would You Do?

Only God can give you the 'True Answer' for your life. Don't allow your 'feeling's to cloud the answers that God is giving you. Simply ask God to show you the 'Red Flags'; ones that you will not miss. Ask God to give you His Peace and to allow only His wisdom and guidance to flow.

Again, God is the only one who knows the truth regarding your life and decisions. Trust Him. :yep:
 
Op, this is a red flag to me. I would not put my business on hold to help grow his. Especially since the only thing you have to go on that your efforts will someday benefit you is him saying “trust me”.

It sounds to me that maybe he is still not sure if he wants to marry you, and this is some way for you to prove your worth to him. If you’ll drop everything, fix his business, and make him some money THEN, he’ll know you’re the one. That’s doing too much.
 
What is his response when you tell him that you are not his wife and can't just be at his place of business all the time?

Yeah. I believe there are times when being frank and open are the only way to know what's what. Let him know you feel unsafe (careerwise) doing this without a safety net (proposal? Or lump sum he gives you?).
This is your life. If you have known him this long just tell him. And clarify what you want in order to help him. If he wants/loves you, he will do whatever he needs to, to make sure you are comfortable.
 
I can't speak to your dudes intentions but your proposed setup sounds like my setup before we got married. The old man was paying me a consultants fee for work I was doing for him and was paying a lot of my living expenses (and my mothers) but he had proposed already and he's always understood that my love language is bribery. I also wasn't deferring anything to do work for him so I didn't feel taken advantage of or like I was losing out on anything.

I don't like that he talks about marriage but hasn't offered it. That does make this feel like some kind of test.

All of that said, surprisingly, If it were me, I would do it and give him a timeline of 3 months part time at your discretion of time you show up. It's a show of faith, you're being paid and you don't leave your sister completely hanging. The selling point is that if whoever it is he wants you to watch doesn't know when you're coming then you'll get to see more things that can be hidden from someone on a regular schedule.

You never give a man everything he's asking for but you can throw him a bone.
 
Op, this is a red flag to me. I would not put my business on hold to help grow his. Especially since the only thing you have to go on that your efforts will someday benefit you is him saying “trust me”.

It sounds to me that maybe he is still not sure if he wants to marry you, and this is some way for you to prove your worth to him. If you’ll drop everything, fix his business, and make him some money THEN, he’ll know you’re the one. That’s doing too much.
This.
 
I can't speak to your dudes intentions but your proposed setup sounds like my setup before we got married. The old man was paying me a consultants fee for work I was doing for him and was paying a lot of my living expenses (and my mothers) but he had proposed already and he's always understood that my love language is bribery. I also wasn't deferring anything to do work for him so I didn't feel taken advantage of or like I was losing out on anything.

I don't like that he talks about marriage but hasn't offered it. That does make this feel like some kind of test.

All of that said, surprisingly, If it were me, I would do it and give him a timeline of 3 months part time at your discretion of time you show up. It's a show of faith, you're being paid and you don't leave your sister completely hanging. The selling point is that if whoever it is he wants you to watch doesn't know when you're coming then you'll get to see more things that can be hidden from someone on a regular schedule.

You never give a man everything he's asking for but you can throw him a bone.
And this.
 
Thanks. That's a another point of view. I was really hoping to also hear from someone who's been in a similar situation.

I really feel like if the pink applied to me, I'd be more on board.

That last sentence is GOLDEN.

So again state what you want. At this point, I don't see the harm in telling him you want a proper engagement first (or whatever your terms are).
I would, but I tend to be unconventional.
Any man (after knowing you as long as he has, and then dating you) should be scrambling to not lose you and making sure you have no doubts.
I'm bothered that he actually asked if he hadn't yet proved himself to you. That doesn't doesn't too good.
 
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I would do it part-time and only if I feel there is a win in it for me. Him proposing would not be a factor. Can you capitalize on having this as a side hustle to help achieve your goals sooner or will it hinder them? Is his business a place you can network to get steady referrals for your real estate business? Will you have direct access to other businesses you’re not usually exposed to for self promotion? Can you pick up any new skills from working there to benefit you in any way?

OAN: Hopefully, you’re still dating other men. It’s interesting he’s been asking you to put you career on hold for months even though you’ve only been dating for eight months. I wonder if he thinks it’s just a hobby for you.
 
Obviously don't do it if you don't want to but he's already generous and you'll be paid for your time. Honestly having worked in real estate I'd do it. I get feeling uncomfortable working for him but I'd be inclined to do it. Real estate is flexible work. You set your hours and determine how much you work. You can also push back on how much you work for him. You can make this work if you want to.
 
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