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Love advice

Chicagoans from three generations sound off on the right and wrong ways to connect in the dating world.

By Jessica Herman Photographs by Martha Williams
Published: February 10, 2009

In a time when a nine-year-old boy’s book on dating, How to Talk to Girls (Collins, $9.99), gets a nationwide release, you can’t discount any opinions on romance on the basis of age alone. That’s why we posed our most confounding communication-related dating questions to three generations of Chicagoans—16-year-old high-school student Tory Moore, 32-year-old online producer Anne Swaney and hip 84-year-old Elaine Fiffer—in hopes of gleaning some timeless nuggets of wisdom.

How much communication should you have with the person you’re dating throughout the week?
TORY I like to talk every day. I like to open myself up, and I find that hard to do if I have limited contact.
ANNE When I’m casually dating someone, I don’t want to talk to you unless you’re calling to ask me out. Don’t shoot me an e-mail saying, “My day was really hard.” Until we’re together, it doesn’t matter. A phone call once a week followed by e-mails and text [in the beginning] when there’s something funny and interesting [is fine]. I would say after a few dates, it’s okay to up the e-mails and text as long as we’re still going out and making phone calls.
ELAINE I guess the nicest way to say it is that if you have something to communicate, then do it. When I was in school, my husband would call and say, “So” [and have nothing to say]. And I’d say, “Sew buttons on eggs.” [But it’s nice] to have someone to talk to about what you did during the day.

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