7+ Reasons Gen X/Middle-Aged App Dating Sucks

My friend Malia is 44 years old and back on the dating scene. We were talking recently about her latest dates. She brought up that men are very different in 2025 than back in 2000.

I did not have anything to add because I have been married 5,000 years. But she had a lot of great insights I wanted to share with everyone 40+ on the dating scene.

1. Men Want to Go Dutch

What is going on men? I am grateful that I am not in this horrid dating pool. What are men thinking?

Millennials and Gen Z tend to talk about money more than older generations. But to request money after is ridiculous.

Millennials and Gen Z also tend to discuss money more frequently with partners than their baby boomer counterparts. That’s partially due to experience: nearly 1-in-5 young people blame “a lack of financial compatibility” for a previous breakup. And many (36%) of Gen Zers see making large impulse purchases as a red flag and potential deal breaker.

With 22% of marriages ending in divorce because of money issues, singles now want to know potential partners’ money personalities before…