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Get Up To Speed On The Dating Game


Are you ready to date again… but afraid of appearing outdated by today’s standards? Whether it’s how to dress more “hip” or learning how to interact with dates through social media, we’ve got you covered!

By Theo Pauline Nestor

o matter what your age when you return to the dating scene, no one wants to seem older than they really are. Maybe nobody ever calls you “miss” anymore or mistakes you for a college student, but that doesn’t mean you can’t still be hip. And a bit of that hipness — as in, wearing cute underwear, knowing your way around a smart phone, and recognizing some music that’s come out since
The ideal profile photo will look and feel like a casual snapshot.
Springsteen’s “Born in the USA” — can shave a few years off you faster than you can say “Botox.”

And why, you may ask, should we middle-aged people try not to act old if we are, in fact, dating people who are also in our age range? The truth is, it seems that young people are having more fun than we are these days. And if we want to take part in the fun, we might need to stop reminding people to bring an umbrella and dressing like we work in a bank to go on a movie date. We talked to Pamela Redmond Satran, author of the hilarious book, How Not to Act Old (Harper Collins), about lots of simple ways that older daters can throw their notions about age out the window and be just a little bit more current.

Before your date…
That initial online impression — your dating profile — is the first place to check for vestiges of old age. Do your photos reek of formality, or do they show you enjoying your life? “Don’t use a formal, posed portrait,” Satran cautions, “no matter how flattering it may be.” She says the ideal profile photo will look and feel like a casual snapshot, “as if you were just accidentally caught in this happy, flattering pose, even if you took it yourself for the express purpose of posting it online.” What are her other tips for taking younger-looking shots? “If you are taking it yourself, hold the camera as high as your arm will reach and look up — but keep your chin down. Don’t be afraid to take several (say, 80 or 90) shots to get one you really like. Clothes, hair, jewelry, etc. should be casual and simple and not [look like you’re] trying too hard.” For women, Satran suggests: “No aggressive cleavage, overdone hair and makeup, or matching jewelry.”

Satran’s book offers a ton of great insights that singles should keep in mind as they’re getting ready for a date, including unstrapping the Rolex (younger people don’t wear watches these days) and investing in an expensive bra that “lifts, separates, streamlines, [leaving you] steady and smooth” in all the right places. “If you’ve climbed out of the suburban spouse-and-mommy pit and are back out there dating, you’ve probably thrown off your ‘middle-age burqa,’” Satran says. “You’re no longer hiding any vestiges of your sexuality under baggy, comfy clothing; at least, you’re not if you have any hope of [getting] a second date! I would say people should avoid dressing as if they’re going to church in overly proper clothing with matched jewelry, shoes and purse… or, for men, wearing a tie and cufflinks.”

In general, Satran says, dating and going out have become much more casual and informal events than they once were: “Movies, restaurants, nightclubs, concerts and dinner parties are more likely places where people wear jeans, say, with high-heeled boots and a floaty top than where they’re going to wear a dress or a suit.” Satran also advises against dressing in anything too sexy, especially on the
Talking about your kids can be a great way to establish commonality.
first date. So that’s a big “no” on the leopard print, leather miniskirts or pants, killer shoes, or unbuttoned shirts with gold chains and lots of chest hair, got it?

During your date…
Your choice of topics and the tone of your conversations (ditch the complaining, please!) can also do a ton of negative work in regards to making you appear older. If every anecdote you tell plays out to the Grease soundtrack, you may be dating yourself. Here are some of Satran’s best tips for putting a more youthful spin on your date-night conversation:
  • “Talking about your kids can be a great way to establish commonality, but don’t let it drag on too long, or it will seem like you don’t have anything shaking in your own life.”
  • “Don’t talk too much about the things you used to do — the trip you took to France in 1976, the summer you worked on the McGovern campaign, Springsteen’s first concert. Of course some of that is OK, but the more engagement with and excitement about what you’re doing now and in the future you focus on, the less old you’ll seem to be.”
  • “Beware of cynicism and negativity. Complaining, criticizing, pessimism — all of this feels old (and is no fun, besides).”
  • “It feels old when people stick too much to small talk and bland subjects, like when they don’t ask questions and don’t reveal [anything about] themselves. Of course, on a first date you don’t want to over-share — but being interested in the meat of the other person’s life and unembarrassed to talk about intimate subjects seems more contemporary.”
If you’ve been out of the dating scene for 20 years or more, knowing the nuances of contemporary gender roles can make you seem more with it. “Today, I think, it’s more usual for men to pay for dates than it was during the ‘70s or even ‘80s, when feminism was a bit more aggressively on the table,” Satran says. “But it is also more normal for women to be assertive about what they do and don’t want from the date and/or a relationship. Sex or no sex, casual or serious, exclusive or open, just friends or friends with benefits — I think there’s a wider range of options now, and women feel more entitled to assert their preferences. A guy who doesn’t like challenges from women (or who’s taken aback by a woman who takes the dating initiative, or insists on no-strings-attached sex with satisfactory orgasms, please!) might have trouble with the new dating landscape.”

As you enter into a new relationship…
There are a number of subtle ways you can adapt to the new millennium’s standards while still remaining aware of differences that may exist between you and your partner as you’re establishing a new relationship. For example, “You can’t count on the fact that your date is on the same age wavelength as you in terms of technology and communication,” says Satran. “How people behave and what they’re comfortable with has a lot to do with their age, including whether they have teenaged or young adult children. Most parents of 20-year-olds are very comfortable texting, but a childless 45-year-old may not be. With voice mail, unless your date is under 30, I’d say it’s safe to leave a message and assume that your date thinks that you will listen to your own messages, too. Email is fine with those over 30 — just don’t let them drag on for too long.” In terms of fitting in with the current generation’s use of social networking, “Wait to friend your date on Facebook and follow him or her on Twitter until your relationship status is more established — whether that means you become a couple or downshift to ‘just friends,’” suggests Satran.


Theo Pauline Nestor is the author of How to Sleep Alone in King-Size Bed: A Memoir of Starting Over and a regular contributor to Happen magazine.
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