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Baby Boomer Love: Important Dating Questions—Answered

23 May 2016

Q: How can I tell if I'm ready to date after a divorce or separation?

A: “When the idea of getting to know a new person feels better than drinking all day or crying all night, you’re probably ready to start dating.” So says Dr. Phyllis, the author of the bestselling book It’s a Meet Market Out There. “If thoughts of dating start with ‘I want’ rather than ‘I should,’ consider this a signal that you're ready to test the waters. But be careful not to get in over your head. Start with your big toe and work your way slowly into the dating pool.”

Q: Should I fudge my age to seem more attractive to prospects?

A: “Dishonesty is the best policy if you care about having long-term relationships,” advises Molly Malarkey, webmistress of SexySeniors.com. “If the person you're dating turns out to be a good fit, do you want to risk your relationship with the truth? Young is in, and the younger you tell others you are the more in you’ll be. Just don’t say you’re under sixteen. Makes you jailbait.”

Q: Where are the best places to meet people I'd click with? I'm so over the bar scene.

A: Dr. Ruth Eastheimer, noted psychotherapist and author of Sex and Death: The First One’s More Fun, says, “Go to real-estate open houses, lectures at the local university, the pool in your apartment complex, group orgies, swingers conventions, whatever. The point is to try new things that interest you but also be open to opportunities in your everyday life. With respect to the people I counsel, group orgies and swingers conventions are part of everyday life.”

Q: What's appropriate when it comes to asking someone out? How long do you have to know a person before you ask him/her for a date?

A: “Try not to impose rules or limits and just go with your gut—unless you have irritable bowel syndrome. Then you should go with a different part of your anatomy.” So opines renowned gastroenterologist, Nathan Nexium. He also advises, “Should you encounter someone interesting and the conversation's flowing at a one-time-only event like a party or a gallery opening, make a move if it feels natural. If it doesn’t feel natural, add some prunes to your diet. That should help you to feel more natural.

“If you're likely to see this person again—at a class, say—wait it out a bit if that feels right. No rush, but don't wait forever either. And remember, a date doesn't have to be a formal, four-hour affair. Getting together casually during the day is a great first date, so what could be easier than saying, ‘Would you like to join me for a quickie cup of coffee?’ If that works out, maybe the next time you can have a cup of coffee and a quickie.”

Q: After my long-term relationship, I'm just looking for fun, nothing serious. How upfront should I be about this on my date?

A: “Let your behavior make your intentions clear,” declares Hetty Friedan, the author of Screw the Double Standard: Why Women Should Be Just as Obnoxious and Crude as Men. She maintains, “As long as your actions and words are consistent with fun—no angling for a home-cooked meal, no pleading for help with household repairs—there's no reason to make a big point of proclaiming time together as ‘no strings attached.’

Relationships are fluid, and you may change your mind and decide that you want to get tied down. If you’re both into rope games, I say go for it.”

Q: How do I tell my grown kids I'm starting to date? I’m worried they won’t approve of me going out.

A: Boston-based psychologist Sharon Horney says, “Simply tell your children, ‘I’m starting to date.’ If your kids respond by giving you a hard time, tell them your doctor has said you have six months to live and you want to enjoy yourself. If they continue to give you a hard time, tell them to stick it where the sun don’t shine. You’re too old for this sort of aggravation.”

Q: What should I wear on a date that's attractive but doesn't seem like I'm trying to look like my son or my daughter?

A: Clothing designer Rolf Lauren says, “To avoid a ridiculous resemblance to your offspring, dress them in old persons’ clothing. Then you can wear the latest youthful styles and you won’t look like your son or daughter. Also, have an idea of what you'll be doing and where you'll be going, so you won't under- or overdress. Have nothing to wear? No problem. Go out with your date to a nudist colony. You’ll save on laundry. 

Q: Who should pay for the date? 

A: Economics expert Alan Meanspan has this advice: “Usually, the person who does the inviting pays for the date, but don't assume. Women should not take it for granted that the man is responsible for the check—and if you're a woman who’s fairly well heeled, it should be your pleasure to take someone out occasionally. Then again, you may be a real cheapskate. If that’s the case, say you’ve left your purse/wallet home when the bill arrives at the end of the meal. The notion that there’s no free lunch does not apply when it comes to dating.”

Q: As a guy, what should I say if my date and I start to get intimate and I have performance issues?

A: Mack Truck, the author of Bed ‘Em Don’t Wed ‘Em, says, “A sense of humor can take you far in this case—laugh it off and your date probably will, too. However, impotence is really nothing to chuckle over. If watching dirty movies or taking Viagra doesn’t work, I’d consider suicide. Who’d want to live with such humiliation!


Martin H. Levinson (Top Five New Mental Disorders of 2015; More Special Interest Groups Required; Praise the Lord and Pass the Ammunition; Baby Boomer Love: Important Dating Questions—Answered) is the author of nine books and numerous articles, plays, and poems on various subjects. He is a member of the Authors Guild, National Book Critics Circle, and the book review editor for ETC: A Review of General Semantics. His website can be accessed at martinlevinson.com.