Hey Doc,

I discovered your columns a couple of months ago and have been addicted ever since. I must say that you have quite a great deal of insight into the male-female thing and I wanted to compliment you. You’re really quite funny, too – I don’t know if anyone’s ever mentioned that. It’s refreshing to see someone deal with dating and relationships in such a lighthearted manner and be so serious and profound at the same time.

Anyway, here’s what I’m writing about. I am a 50-year-old man. I’ve had a crush on Sienna since I was 12. (I know this sounds weird, but it’s true.) She recently lost her parents, who she cared for because they were elderly. Sienna is 51, was never married or had kids. I recently discovered her profile on a computer-dating network. Years ago she used to be plump and had very poorly dyed hair and bad teeth. Now she’s drop-dead gorgeous. Her hair has been done beautifully, her teeth have been fixed and she’s lost 105 pounds! In other words, she’s had a very expensive makeover. But here’s what disturbs me. Sienna is saying on her profile that she is 37 years old, and I have to admit that she does look like she could pass for that age. She doesn’t know that I know about her deception, by the way.

Sienna and I have not been in touch for a long time, Doc, but I could never get this woman off my mind. We never had a romantic relationship, by the way. I feel that this is the time to finally try and make something happen, but I keep thinking about the fact that she’s lying about her age.

Do you think that it’s ever too late to hook up with someone that you’ve always been interested in? Would the fact that she’s lying about her age disturb you? Can you give me some coaching?

Remington - who was shocked to see the new her

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