Dear Prudence,
My best friend keeps dating much, much younger women, and I worry it’s holding him (and them) back. I’ve known my best friend for over 22 years, and even though we’ve lived apart since high school, we keep in touch. We’re in our mid-thirties, and have led fairly different lives on different coasts. He recently completed a big accomplishment, so I traveled to be there for his commencement. He introduced me to his new girlfriend, just 20 years old—he had kept it quiet for months because he didn’t want me to lecture him. I kept things brief and positive and was friendly in our introduction. It was the first partner I met, but this is at least the 4th or more intended-to-be-long-term relationship (major financial and career decisions revolving around them) he has been in with a 20-year-old in the last decade. He also admitted to dating a 19-year-old in the last year. We bonded in our teens over a history of abuse and overcoming significant challenges, some of which he knows occurred between myself as a young woman and older men. I don’t see him as a controlling and manipulative person, but I do think there’s a serious caregiving need that’s better for therapy than a relationship. I have recommended therapy often. None of these women have ever interacted with me, but it feels wrong. Do I press the point on this one, or stay in the background because they are all adults?
—BFFs with Leo-Wannabe