Dear Old Guy welcomes letters on all subjects, including love, marriage, child rearing, even basic plumbing and medical advice. What he doesn’t know, he is happy to make up. After all, he’s just an opinionated Old Guy.

Dear Old Guy,

  I am 50 and have a new boyfriend, Harry.  My family doesn’t like him and they don’t want me bringing him to any family functions. So far I’ve been making excuses to Harry but it’s becoming obvious to him that he isn’t welcome. Any recommendations?

Signed, Why Not Him?

Dear Why Not,

Are you kidding? I’ll bet this isn’t the first guy you have introduced to them as the one. Maybe your family is getting a little tired of all your bad choices. My guess is you should trust the mob’s instincts about this guy rather than your own… after all it’s unlikely your family is as needy as you. —O.G. 

Dear Old Guy,

I am 16 and dating a 19 year-old boy Mike who really likes me a lot. My friends all know him and warn me he’s a bad seed.  I’m not too crazy about him but he says he’ll kill himself if he loses me. This has me worried and confused.

Signed, Have To Keep Dating

Dear Have,

Ah, emotional blackmail. I am sure this loser has dated others who managed to get away… and still he lives. Run for the hills, kid… —O.G.

p.s. you may eventually need your parents to take out a restraining order against him.

 Dear Old Guy,

I am in my 40s and have been dating a guy over the Internet. He says he loves me but so far he is unwilling to meet. Oh, I’m a guy, too. Please tell me what to do.

Signed, Digital Lover

Dear Digital,

You’re kidding, right? Do you know how dangerous Internet dating is? First of all, for all you know, this supposed middle aged love interest could actually be an 11-year-old girl who is out to rob you or worse. But seriously… chatting with someone over the internet is not dating. Dating is about meeting face to face and learning to dislike them that way. If you don’t understand, then I recommend professional help… but not on the internet. —O.G.