Dear MIMsters: Is this Behaviour By My Would-be Fiancé a Red Flag Or is He Testing Me?

My boyfriend and I have been together for the past 2 and a half years now. He claims a bad experience in the past involving another woman who broke his heart has shaped his mindset towards our relationship. In the area finance, that is. I just want to know if his behaviour is a red flag or is just testing me.

I would say he doesn’t support me financially as a normal boyfriend would. Even though I’m working, I’m struggling financially while he’s financially sound.

The few times he’s given me money was when I lost an auntie and was leaving to my hometown for the funeral. And the last time he gave me money was 6 months ago, when I was really busted/broke because I had to used all my money to rent and furnish an apartment.

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Even at that, I had to ask him before it was given to me. Honestly speaking, that money he gave me lasted for only a week. I’m not an extravagant person because I manage finances very well. It is just that my salary is nothing to write home about.

When I got the apartment and finally settled down he told me he was going to give me back every dime I spent on the apartment. That was a relief for me. But it’s being 6 months now since I got the apartment and he hasn’t reimbursed me as he promised.

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However, he’s said it in passing for a couple of times that he’s waiting for some bonuses to be paid before he gives me the money.

My main concern is that he doesn’t support me on any financial level like with feeding, my hair, sanitary products, toiletries, bills, grocery cloths and all that you can think of. Meanwhile, I make sure he’s well fed whenever he comes to my place.

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Prior to our relationship, he had a lady that he sponsored to the UK. According to him he spent $72k on her that was 4 years ago. Unfortunately for him, the lady broke his heart with infidelity so he ended the relationship with her.

Now, I need your candid opinion on this; is his attitude towards me borne out of his past experience or is he just naturally stingy? If his attitude is borne out of past experience, will he change when we get married?

I need to make a decision now as he is asking for my hand in marriage this September. He’s come to to do an official introduction already though.