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Dear Goldy,

My son is 28 and began dating an older woman. She’s 33 and divorced. I don’t think my son needs to be dating older divorced women yet. He’s young enough to see what single girls his age are around. If he were in his mid-thirties, then I don’t think I’d mind so much. But to do it in his twenties seems too soon or rushed.

Dear Goldy,

I don’t know what to do. I don’t want you to think I’m a monster, or not kind or not understanding... or any of those things. And because of that, I haven’t discussed this with anyone. Maybe you can help.

Dear Goldy,

I know never to look a gift horse in the mouth, and I never have, but at my family’s Chanukah party, I couldn’t help myself.

Dear Goldy,

I’m a big fan of yours. I love reading your articles, and sometimes we discuss them around the Shabbos table. My family laughs or they are shocked at what people write in about their dating lives. I (and others) like how you answer the questions as a friend would answer a friend. You say it straight. You’re never harsh, but you are blunt—and I think that’s what makes you different from others who are preaching and teaching about the shidduch parshah, what’s happening in and to this generation, and why “there are so many more older singles now than there were decades ago.” When speaking about shidduchim, I like real advice and real experiences—not “It says in Mesechta Tet Vav...” or “When Avraham was trying to marry off Yitzchok...”

Dear Goldy,

My family isn’t rich. We’re middle class, maybe in the middle of middle class, if I had to label it. My siblings and I started working as teenagers, and we’ve always bought what we wanted. Our parents took care of our needs, but if there was anything special any of us wanted, we’d pay for it ourselves. After high school, I seriously started thinking about saving for my wedding.

Dear Goldy,

I don’t want to come off sounding conceited or snobby, but I will no matter how I word my letter. B”H I come from a well-off family. Yes, I have a PhD.