It’s a family affair

I always feel a little goofy giving interviews to members of the media (I’m usually the one asking questions), but I got an interview request the other day that was actually pretty fun. Phillip Milano, who writes the “Dare to Ask” column for The Florida Times-Union, wanted to know if I would be his “guest expert” for the week and answer a question from a 36-year-old Jacksonville, Florida man. The guy’s predicament?

I’m 36 and just broke up after three months with a very sweet 20-year-old, Michele, who was simply too young for me. … Her mother, Linda, is 37, divorced and as sweet as her daughter. I know Linda is very attracted to me, and though I think we’d make a great couple, we haven’t said anything yet to Michele … Is it wrong for me to pursue Linda now that my relationship with Michele is over?

That’s right, he wanted to know if it was kosher to date (and do) the daughter and then turn around and date (and do) the mom. Call me old-fashioned, but I thought this was a little over the top (here’s a link to the column with my suggestions for Doug, the dating machine). Seriously, who’s next — Grandma?  Great Aunt Ethel? 

The guy’s question did get me wondering, though, as to how many people find themselves in the same situation. I’ve never been attracted to more than one member of a family at a time, but way back in high school, I had a girlfriend who dated two brothers. Of course, in her situation, she did it accidentally, i.e., she thought she was dating the same guy (they looked alike, okay, and, yes, there was some alcohol involved).

How about you? Have you ever fallen for some older guy and then found yourself making goo-goo eyes at his 20-something son? Or started dating a woman and then realized you liked her sister better? If so, what happened? Did you ignore your feelings of lust? Pursue the forbidden fruit?  Personally, it seems better to move on than risk a huge family feud, but maybe there are circumstances where it’s all worked out in the end. Whatever the case, sounds like the makings for a hell of a family reunion.  

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6 Responses to “It’s a family affair”


  1. 1 Sam December 10, 2009 at 4:50 pm

    My dad dated my aunt before my mom… her sister.

  2. 2 singleshot1 December 10, 2009 at 5:01 pm

    Wow, I’d love to know more, Sam. Was there ever any weirdness? Or did it just turn into a favorite family joke after the wedding?

  3. 3 Phillip Milano December 11, 2009 at 11:44 am

    Sorry I didn’t tell you sooner that the column published! Diane you gave a fantastic interview and set my readers straight about this one! All the best to you. I told my mom about this guy’s question and she was like, “that’s disgusting.”

  4. 4 singleshot1 December 11, 2009 at 11:52 am

    Thanks for the nice words, Phillip. I’ll do an interview like that any day! With you OR your mom. ; )

  5. 5 Jennifer Worick December 16, 2009 at 11:02 am

    A couple of things. I recently dated a much younger guy, who broke things off because the age difference got to be too much for him. He told me that he once dated a chick and his brother dated her mom and it was just weird. Well, duh. Age is the least of that problem. And then, on a separate note, my mom dated a guy once who broke things off because they weren’t the same religion (it was the early 60s). So he handed her off the to Catholic guy across the street. That was my dad. They weren’t family but I thought it was weird.

  6. 6 dana December 18, 2009 at 5:02 pm

    it’s funny how these things happen. I’ve heard of guys who move on to a younger sister, when the elder grows out of him. Even know a woman who was her best friend’s Dad. Creep me out. But this mother daughter racket is odd. First of all, what was he doing dating that child? 20 is very young. Secondly, the mother had that child at 17. This is a bad sign for good judgment. Oy! And then there’s the Woodman. “The heart does what the heart wants to do….” ‘Nuf said.


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What’s the story?

Meet Diane Mapes, your friendly neighborhood freelance writer. My beats include health (with an emphasis on cancer prevention, treatment and survivorship) and lifestyle and singles issues, but I also love writing about history, natural history, pop culture and TV/film. On this site, you'll find links to stories, praise for my writing (*blush*) and the odd bit of social commentary about the single life. Also here, a few shameless plugs for my books (hint: see links below). Have fun, glad you're here and hope to hear from you soon.

Oh! And if you're looking for my breast cancer blog, go to Double_Whammied

Check out my books!

How to Date in a Post-Dating World A dating manual for the modern, mangled single.

Single State of the Union
Single women speak out on life, love and the pursuit of happiness.

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