First Dates In Your 50's…

Sure, you’ve been around the dating block a few times, but you can still benefit from some advice, right? Try these proven tips.

By Chelsea Kaplan

aybe you’ve recently gotten divorced or been widowed and it’s been ages since you went on a first date. Or maybe you’re back dating again after just a year or two “off the market”… but wonder if the rules of the game have changed. Regardless of which scenario applies to you, having a successful first-date experience is not only well within the realm of possibility; it’s easier than you think. “By following a few simple guidelines, acing your first date when you are in your 50s can be a breeze, even if you’re terribly nervous,” says Terri Orbuch, Ph.D., the host of Detroit’s popular “Love Doctor” live television and radio programs. Let Dr. Orbuch’s tips help you find the right people to date—and enjoy the process.

1. Make sure you’re ready
Contrary to what your friends may tell you, Dr. Orbuch notes that studies show there is
Online dating is a great way to get a jump-start and find new prospects.
no predetermined time period that you need to wait after a divorce or loss before you start dating again. “There is no hurry, so take your time before you enter the dating world again,” she advises. Just because you are in midlife, doesn’t mean you’re in a rush. A good litmus test: Ask yourself if you are truly ready to commit to and care about another person. If so, you’ll undoubtedly enjoy dating much more. If not, you may find yourself approaching dating with a neutral-to-negative attitude and therefore are not presenting your best self to those you meet.

2. Remember: Similarities, not opposites, attract
When you’re first re-entering the dating scene, Dr. Orbuch says it is very common to be attracted to the “wrong” type of person: “Typically, this happens because you are fascinated with people who aren’t like you. You may feel you have to hurry up and try dating someone radically different. Ultimately, however, the best match for you is someone who is more similar to — as opposed to different from — you, especially when it comes to underlying values.” This holds true for all ages. So, when evaluating a potential date, make sure he or she feels similarly to you about the things you value most, such as family, your politics or attitudes concerning financial issues. If you don’t match up, it may be wise to end the date after dinner and not put yourself through several evenings of mismatched conversation.

3. Reconsider where you look for dates
“Contrary to popular belief, the best place to meet someone is not at a party or bar,” Dr. Orbuch notes. Indeed, those places tend to work against baby boomers, who are usually looking for a deeper connection, while 20-somethings may be fine with the freewheeling socializing those spots encourage. Instead, Dr. Orbuch advises boomers to pursue a regularly scheduled activity, such as a book club, volleyball team, a volunteer project or religious group. “In these types of settings, you can meet and spend time with people of similar interests on a consistent basis,” she explains. And yes, you should ask your friends and family to fix you up, she asserts: “These types of meetings really, truly work; it is a total myth that blind dates are only for people who are desperate!”

4. Don’t put all of your cards on the table
Many people make the mistake of disclosing too much information when on a first date, often due to nervousness or sheer lack of practice at dating. Or maybe you’re thinking that, being of a certain age, you don’t have the patience to play games and want to “let it all hang out.” Don’t, say the experts. Instead, disclose personal things gradually over time, advises Dr. Orbuch. “If your date is the right person for you, there will be plenty of time for ‘your story’ to unfold, and that will make you endlessly exciting and interesting to him or her, rather than overwhelming,” she says.

5. Don’t discuss past relationships or marriages
“Divorce and breakups leave everyone — even the most mild-tempered — with a
Avoid mentioning your ex and going into detail about your baggage…
degree of bitterness,” asserts Dr. Orbuch. “Your date does not need to be drawn into your negative state, nor should you be dwelling on it right now.” Though it may be tough, avoid discussing your ex-spouse and why your marriage didn’t work. Similarly, don't go into your legal woes, money problems or custody battles. “If revelations are necessary, make them as brief and neutral as possible,” Dr. Orbuch suggests. Talk about what you’ve learned about yourself and your relationship goals rather than regale your date with “Can you believe it?” tales of woe.

If you have experienced the loss of a spouse, Dr. Orbuch says that while making comparisons between your date and your former spouse are natural and common, it’s best to try to remember that no one will compare to him or her. Additionally, though your former spouse may be ever-present in your mind, Dr. Orbuch notes that your date may feel uncomfortable hear about your deceased spouse at such an early point in your new relationship.

6. Don’t rush judgment
Dr. Orbuch notes that while it’s awfully tempting, it is almost impossible to make a sound decision about someone on a first date: “Sure, sometimes the chemistry is so lacking that you know immediately that you could never have sparks, but it usually takes a while for people to unfold.” Even if your date seems like a dud, be open and remember not to rush to judgment—some of the greatest love stories ever told began poorly. First-date nerves can get in anyone’s way, whether the person in question is 25 or 55… consider having a brief coffee date again in a week or so to see if things look any different at that time.

7. Be open to online dating
Consider the possibility of meeting someone wonderful over the Internet, Dr. Orbuch says: “Online dating is a great way to meet people—especially if you are shy.” While it barely existed a decade ago, it’s now become one of the most popular ways for couples to come together. You can search for people whose interests and attitudes match your own—and whose path you might not otherwise cross in daily life. Take your time, build a rapport online, then have a phone call or two before meeting. The idea is to gather information to make sure this person is worth some face-to-face time.

And, of course, use your usual first-date common sense when you do meet, says Dr. Orbuch: “Plan your first meeting in a public place. Get to know each other before you bring a date to your home. This is for two reasons: One, for safety’s sake, and two, you may want to give things a bit of time before you start showing off your almost-empty refrigerator, hyperactive dog or messy house!”

Chelsea Kaplan is deputy editor of and regularly appears as a guest on XM Radio’s “Broad Minded.” Her blog, “I’m Somebody’s Mother?” can be found at
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