Question for the single ladies

My question: what is considered the preferred channel to encounter and get in contact with single ladies in the 30-50 age group these days in Indianapolis?

I've been out of the dating scene for 5 years and I'm trying to help my male friend, age 42, improve his chances of creating a lasting relationship. Back in the pre lockdown world it was the norm to have a profile on all the dating apps but I ultimately found my love offline at a bike party.

My friend doesn't like the apps and his main method is buying women drinks at downtown bars, so far with zero success. He has a great sense of humor, runs his own business, his politics are progressive, he is 6' and has a pretty muscular build, he dresses modestly (recently wore a red plaid collared shirt), his friends are all normal looking, yet when he goes out women just tell him "not interested". It seems like a new approach is needed, I want to help him but I'm out of ideas.