I want to HUMILIATE my sister who is a single mother

I don't date single moms. However, I usually don't go around and announce it because I know a lot of women -- including my own sister -- are triggered by it. There is no reason for me to be going around looking for confrontations. The problem is my sister who is a single mom, (atop of being a twice divorcee.) I have directly told her that I do not date single moms or divorcees because I do not want to hurt her feelings or make her feel like I am putting her down.

I am in my 40s, have never married or do not have any kid. I think I am doing pretty okay. I own my own business, used to teach part-time at a good college before the pandemic, have my own house and rental properties. I made about $250k in 2019 but only $120k in 2020 due to the pandemic. My mom and aunts were pressing me to get married when I was in my 30s, which drove me nuts. However, they have pretty much given up and stopped a few years ago.

My sister "ambushed" me and set me up with a single mom, (just before I turned 40, at the time she was married to her second husband.) Neither my sister or her friend told me that the friend was a single mom. I found out just before our third date, which I then called off. My sister found out and was obviously not happy. Frankly, I think she was helping her friend more than she was trying to help me. Anyway, I told my sister to not to try to set me up with anyone again.

I have been seeing someone in her 20s for three years. I would have prefer someone closer to my age, but my more important preferences/priorities are: no kid, and no previous divorce or marriage, and it is difficult to find a woman near my age who also meets those criteria. I did not tell my sister about my girlfriend because I knew she would be upset that I was dating a much younger woman. My sister -- who is now divorced TWICE -- tried to set me up with another one of her friends, (even though I had told her not to do it again.) Again, the friend is a single mom. I did not want to meet her friend, so I finally told my sister that I was already seeing someone and have been with her for over three years. Obviously my sister wanted to know more about her.

Since then, my sister has been criticizing and talking s**** about my girlfriend, NON-STOP. It has been getting on my nerve. My sister keep saying my girlfriend is too young for me, that she is not good enough for me, (mostly due to education: my girlfriend has never been to college.) My girlfriend also used to worked as an online streamer in Asia when she was in her early 20s, i.e., chatting and dancing online, yes, guys are stupid enough pay for that; however, it's not like she stripped or got naked or had s** with any of them. I did not meet her through online but I knew what she did because she told me herself the first time we met. However, my sister found out about it and talks about it as if my girlfriend was a prostitute or doing s** work.

My sister basically wants me to dump my girlfriend, who is young, look good, fit, feminine, enjoy being with me and I being with her, and MOST IMPORTANTLY, has NO kids and never been married. Just so I can date her single-mom friend whom she wants to set up. My sister's only selling points for her friend is that she is near my age and at the same education level as me. (Seriously I do not care about any of that. And she is not really at my level because I have a master.) So far I have tried to be nice to my sister, but she has been RUDE, INCONSIDERATE b**** when she herself has qualities that most men would consider as unattractive and deal-breakers. The truth is, in terms of quality as a woman and what they can offer to men, my girlfriend is way above my sister. I really just want my sister to STFU. It is getting to the point that I just want to lash out at my sister, tell her what men really think about single moms like her, and just to bring her down a few notches so she can learn some humility, (but I doubt so.)

3 days

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  • Why don't you ask your sister to have sexual relationship with you. This might solve the problem for both of you.

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