If they asked for money twice or more in a relationship, isn't that a red flag?

Personally, I don't like asking for money. I find it awful to be asking for money.

I once had a boyfriend that asked me for money twice. The first time it was for $600. I obviously refused, said no and told him ''I'l let this one slide and pretend this conversation never happened. Ask me again and we're breaking up''.

He asked me again ($300) 4 months later and I proceeded with my words. I broke up. Seriously isn't that a red flag? Someone that wants a serious relationship that will progress would be working on themselves, be able to take care of themselves, not ask for money, much less large amounts.

Updates
+1 y
I think the only exception would be if he were my husband, we're really struggling and are providing for children. Ok then I'll help in what I can but for a boyfriend that I'm just dating? NOPE
If they asked for money twice or more in a relationship, isn't that a red flag?
Post Opinion