Why do some successful men date women below their caliber?

NSFWMen’s Input Only

Please don't judge me with what I am going to share and don't lecture. I know it's messed up. I am a 50 year old professional woman who is above average looking. I don't look my age and have had dated wonderful successful men. I have had rich and famous men hit on me and date me. I am told daily I am beautiful by men and women. I know this sounds obnoxious but it's true. I take care of myself and I have good genes. I'm fortunate and don't take it for granted. I have been married to a nice man for 20 years.

25 years ago I dated a famous person. Let's call him FP. We saw each other long distance (he in NYC, me in California). We dated for 3 years until he told me that his ex was pregnant. He wasn't sure it was his or the cop she was sleeping with who lived with his mother!

While I was hurt, I was supportive of him. Turns out, the kid was his. I knew I had to move on.

I still was seeing FP occasionally and met my husband to be. I told FP that I met this man and it was getting serious and I asked him how he felt about it. He told me he loved me, but wasn't ready for a commitment.

When I was proposed to, I went to NYC to tell FP in person. The chemistry between us is insane and we saw each other a couple of more times.

Fast forward, we agreed to just be friends. My husband knew that FP and I were friends and he wanted to meet him. We went to NYC and it was great. We were finally just friends...I thought.

Then a couple of months later, FP came to our city and the 3 of us had dinner. Long story short, FP pushed my husband out of the blue down on the ground. He was drunk. I called him the next day and his explanation was that my husband took me from him. I stopped communicating with him for 15 years.

2 years ago, my husband got ill and nearly passed. I reached out to FP and told him. He was very supportive.Over the last 1 1/2 years we started an emotional affair and spoke weekly. I was traveling last week and we saw each other and slept together. I don't feel bad. It was amazing. I still love him.

Here's the craziest part: he said he wants us to be each other's side piece. He's living with a woman he used to see but is not attracted to her. She has 3 kids and is fat and they don't have sex. I asked him why he's with her- he said "who else is going to take care of me". Prior to that, he almost married a woman with vaginosis and she stunk so bad, it could be smelled through her jeans. She was also physically abusive with him. Prior to her he dated a woman that he said was so dumb, she didn't know Thanksgiving was on Thursday! Let's not forget the woman he had the kid with who was with a grown man who lived with his mom.

Last weekend he told me that it was the first time in 2 years that he fucked a woman as he couldn't stay hard. That he felt safe with me and that I still turned him on and he loved my body. He was proud of me. I have never hurt him, we have amazing chemistry and I know that looking your best is important and men are visual animals. Why in the world does this Uber successful rich and famous man continue to see woman who honestly shouldn't even be in the same room as he is!

He said he was always proud to have me on his arm...how much I turn him on and how much fun we have together and can talk about anything. What do they have that I don't have? I don't get it.

Posted May 11, 2025, 4:52 PM UTC

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