Pillow Talk: His best friend's sister

CHICAGO -- Tuesday's question comes from Anonymous.

He wrote: "Recently, I've been hanging out with my 'Lil sister.' She is the sister of my best friend and I've known her since she was 5 years old. I'm 10 years older than she. We are now over 50-years-old. We've been going out to clubs and restaurants and just having a good time enjoying each other's company. The problem is that I'm beginning to have some 'feelings.' I would never jeopardize our relationship, but I don't know if I should say anything."

Ryan, Val, Ji, and comedian Damon Williams weighed in.

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