Giving an acquaintance $500

[Cinderella]

My boyfriend has a female “acquaintance “ who asked to borrow $5000 but he said he didn’t think she would be able to pay him back, so he just gave her $500. Now she gave him a birthday gift that is on display in his bedroom. He says they are just acquaintances,yet she only comes around when I am not there. He has also taken her to casinos and pays for her gambling. He swear that he has never been with her in a romantic way. If I say anything he gets mad. Am I being a fool?

[Acacia98]

You are right to be concerned. You clearly are not on the same page about how people in committed relationships should conduct themselves. And it really is a waste of time to try to convince adults to change their beliefs and behavior. If I were you, I would quietly remove myself from the relationship.

[ShyViolet]

It sounds to me like your bf thinks you're an idiot.  This all doesn't sound right at all and you shouldn't just go along with this.

[Sanch62]

4 hours ago, Cinderella said:

If I say anything he gets mad. Am I being a fool?

Yes, getting mad is his way of shutting you down and treating you like a fool.

You can do better. Skip him.

[ExpatInItaly]

She's clearly not just an acquaintance. 

I wouldn't date a man like this. He's not being honest with you. 

[Gaeta]

Yes you are a fool. 

There is no way l would date a man that does that. Most people would not accept this behavior in a relationship. If l gave $500 to a male acquaintance and went to casinos with him, and paid for him, my bf would tell me good bye!

[BaileyB]

What do we know about this guy - 

1- He is not financially responsible.

2- He disrespects his girlfriend and dismisses your feelings.

Do you consider those dealbreakers in a relationship? I would.

 

[Sony12]

Is this female friend an escort?

[Cinderella]

Thanks all for confirming my thoughts. I have known this man for over thirty years. He actually set me up on a blind date with my husband who passed away, six years ago. It is so difficult breaking away from him because I really do love him. I do realize this is not a healthy relationship and I feel like I am the only one trying to keep it alive.

your comments are giving me the strength I NEED TO MOVE ON. THANK YOU!

[MsJayne]

On 7/12/2025 at 7:53 AM, Cinderella said:

Am I being a fool?

No, but you're being way too tolerant of his dismissive attitude towards you. If he's your actual boyfriend part of that is that he should respect you, and he obviously doesn't if he gets snarky when you question his behaviour. I'd have a whole plethora of questions for him, like why haven't you met this "acquaintance", why is she hitting him up for money, why is she buying him gifts if she's so broke she's borrowing money, is she someone he'd like to be in a relationship with but she's not interested in anything other than friendship, and the biggest question of all, why is he using this person to make you feel uneasy? Sounds a lot like triangulation, and that's a behaviour that should tell you to cut him dead. What was the birthday present she gave him that he proudly displays in his bedroom so you can look at it every time you go in there? 

[Cinderella]

It was a stupid reflective smiley face plaque. I have met her and she doesn’t care to engage in conversation with me and he gets all distant. I am through. I deserve a better relationship!!

[MsJayne]

5 hours ago, Cinderella said:

It was a stupid reflective smiley face plaque.

Ew, tacky ! This in itself is a good enough reason to dump him. 

[ThorLyonsSalem]

I am so sorry that this guy is doing this to you. You have to ask yourself why it is that you are allowing this to overtake you, because you can do better than someone who lies like this.

Kick him out and don't look back. 

 

[Cinderella]

So far, I am staying away from him. His daughter's family will be in town this weekend and I  plan on getting together with them. She knows I don't want to see, so I  hope that goes well. We are close and I love those grandkids and don't want to lose the bond we have. Wish me luck! I REALLY DON'T WANT TO SEE HIM!

[ExpatInItaly]

I would not go to this family event. 

Instead, I would break up with him. They will underdtand why you're not there if you two are no longer together.