Ask The CLO - 05.20.25 - Best of The Steve Harvey Morning Show

Ask The CLO - 05.20.25

Darius in Southaven – I’m a country boy and I have had a roofing company for about 10 years. I make good money and I think that is why women want to date me. My mom said I’m dating out of my league. How do I figure out if they like me or they like my money?
Rachel in Landover – I’m 27 and my boyfriend is 29. His parents are pressuring him to propose. His sister told me that they gave my boyfriend his mother’s first engagement ring. I don’t want that tiny diamond. What do I do if he proposes with that antique ring?
Harrison in Poughkeepsie – As a grandfather of 3 girls, I’ve taught them how they carry themselves like respectful ladies. Their mom, my daughter, told me to mind my business. These girls don’t have a father figure. Should I keep applying pressure or leave it alone?
Alma in Toledo – My neighbor called and asked if I had a red shirt she could borrow. I barely know her but she said it was for a first date, so I gave her one of my newer shirts. She returned it without cleaning it. Do I tell her to dry clean it or use this as a big lesson?

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