Returning to the Dating Scene

Don’t let fear prevent you from finding love again in midlife.

Medically Reviewed by Charlotte E. Grayson Mathis, MD on April 01, 2007

Whether you're bouncing back after a divorce, or recovering from the death of your life partner, returning to the dating scene is never easy.

Indeed, from the challenge of meeting someone new, to wondering if he'll call again, to those inevitable questions about sex and intimacy, the prospect of getting back in the groove can seem downright daunting.

The important thing to remember, however, is that almost every woman shares at least some of that same anxiety. Moreover, if you do want to start dating again, you won't have to look far to find companionship!

According to the online dating company,, baby boomers are its fastest-growing group of members. Indeed, many in this age group are divorced, single, or widowed, and now find themselves back out on the dating scene for the first time in years.

Now, if you have a happy and fulfilling life without dating, you shouldn't feel pressured into a social scene that's not right for you. At the same time, if you're craving adult companionship and maybe even a little romance, don't be shy about filling those needs -- and the dating world is an excellent place to start!

To help you along the way, WebMD offers these tips from the experts on how to get started.

You've decided you want to try dating -- now what? How do you meet eligible people? Should you try online dating or do it the old-fashioned way, finding dates through friends and acquaintances?

San Francisco psychologist Jonathan Rosenfeld points out that dating is a numbers game: You're probably going to have to meet a lot of people before you find someone you really like. "If you are a busy adult with work you're committed to, and children at home, then you have to make dating efficient," Rosenfeld says. "And there is no more efficient vehicle than the Internet."

"Remember that you are looking for a good fit, not validation," Rosenfeld continues. "Many people make the mistake of putting out a generic profile that will attract a lot of people. But if you do that, you're going to attract a lot of people who aren't a good fit, and that can be exhausting - and demoralizing."

Instead, says Rosenfeld, when you are creating your online profile, "Avoid generic likes and dislikes, like walking on the beach," he says. "Don't be strident or negative, but don't hesitate to state strong beliefs. Don't be shy about saying who you are. You may get fewer responses, but you're likely to be more compatible with the people who respond."

Whether you're dating online or not, it can't hurt to also let friends, family members, and acquaintances know that you're available and want to meet people. There is no guarantee that you are going to like your sister-in-law's newly divorced first cousin, of course, but the connection ensures that your date is not a complete unknown.

Once you've made a connection -- either online, through friends, or by striking up a conversation with someone in the grocery store -- and you've arranged to get together, there are some important things to remember.

1. Meet on neutral territory. Arrange to meet at a café or restaurant rather than at your home or his. If you have made a connection online and know nothing about your date, you may want to be extra cautious by letting a friend know where you will be meeting and at what time.

2. Keep it short and sweet. For your first meeting, it is best to arrange a coffee date rather than a dinner or an afternoon at a museum. If you don't seem to be hitting it off, it's easier for both parties when there's a quick escape route! Moreover, to help ease the anxiety of a first-time date, Rosenfeld suggests you "sandwich" the meeting between two other activities you really like.

"Before you meet your date, do something that puts you in a positive frame of mind; then, after the date is over, meet up with a friend," he says. If the date is a disaster, you'll have someone to commiserate with. And if it's great - you'll have someone to celebrate with.

3. Keep the conversation casual. This is not the time to discuss your favorite baby names or your ongoing feud with your ex. There will be plenty of time for such discussions if you continue dating, but a first meeting should be light and breezy. Ask about his interests and how he spends his time, and share the same information about yourself with him.

4. Don't forget to have fun. Don't pressure yourself into deciding if this is the person you want to grow old with -- remember, its just coffee! Try to make the outing entertaining and interesting -- for both of you. Jonathan Rosenfeld suggests that people view dating as an adventure. "Everyone knows that adventures have ups and downs and they expect that," he says. "If you think of dating the same way, you are less likely to be disappointed."

Assuming you and your date "hit it off," invariably the question of sex will arise -- sometimes as early as the first date. What's important to remember here is: It's your timetable. So, don't hesitate to slow things down if your date is ready, but you are not. There are no "shoulds" when it comes to dating at midlife and physical intimacy, and you have a right to go at your own pace.

When the time arrives that you do feel ready, when, how, and where is less important than basic safety. If you've been out of the dating scene for some time, you may be unfamiliar with the essentials of safe sex. The message is simple -- and urgent: Always use a condom. Whether or not pregnancy is a possibility, you need to make sure you are protected from HIV and other sexually transmitted diseases.

San Francisco relationship expert and writer Mera Granberg advises women to carry condoms if there is any chance they will be having sex. "Many women I talk to are afraid to carry condoms because they don't want their date to think they are a slut," she says. "But it's your health we're talking about, and you have to be a grown-up. If your date can't handle the fact that you want to protect yourself, you probably aren't interested in him anyway."

If your relationship continues -- and it's an exclusive arrangement for both of you -- unprotected sex might be OK but only after you both get tested for sexually transmitted diseases -- and wait for reassuring results. Experts warn not to take risks, no matter how convincing your partner may be. If you're not certain about any aspect of protection, talk to your doctor, or ask a trusted and well-informed friend.

Although most experts say dating is much like riding a bicycle -- you never forget how - it also means that a bump in the road can lead to a nasty spill when you least expect it.

To help ease the transition from newly single to coupling up again, here's some additional advice that can help.

Take it slow. Don't pressure yourself to make any decisions after a first date. In many cases it will be crystal clear that there is no connection, in which case you can tactfully explain this before the date ends, or in a follow-up phone call or email. If you aren't sure if the chemistry is there, and want to see the person again, go ahead -- it can develop over time. In most instances you should know within three or four dates if this is a relationship worth pursuing.

Consider your children. If you have children, it is important to keep their needs front and center. This means protecting them from adult issues and disappointments. Your children don't need to know all the ins and outs of your dating life, and they don't need to meet your dates until you are certain they will be playing a significant role in your life. When the time comes, arrange for a casual meeting but keep it short. Experts say it's not a good idea to bring anyone into your children's life until you are certain they'll be around for a while.

Get the memo. This is a phrase coined by Mera Granberg to describe the importance of listening to your date -- and really hearing those subtle but revealing things he says that are omens of what's to come. Granberg contends that whenever we meet a new person, there is always a memo, whether we want to hear it or not.

"It can be something as simple as 'I'm not very good at relationships,'" Granberg says. But that little "memo," says Granberg, is an indication of who he is and what's important to him, so pay attention. Keeping your eyes and ears open can prevent you from building illusions that will come crashing down later on. "When I look at all my relationships that went south," Granberg says, "I can find the memo and I always got it early. But I didn't actually read the memo." Paying attention to a potential partner's messages, she says, is the best way to prevent a dating disaster in the making.

While some women find it easy to end one relationship and start another, for others letting go -- and starting again -- can be difficult and painful. Indeed, experts say that sometimes it's better to allow some time to pass between a failed relationship and the start of another one -- time that can help you reflect on what you really want and need in a partner.

As clinical psychologist Rosenfeld says, "You need to understand why your marriage or previous relationship didn't work. If you don't, you are at high risk for repeating the same mistakes again."

One clue: If you find that you are particularly nervous, uncomfortable, or reactive, or if you find yourself making constant comparisons between your ex and your date (even in your own mind) you may not be quite ready to get back into the dating scene just yet. In which case, experts say, give yourself a bit more time to and then try again.

One of the great advantages of adult dating is that you bring maturity and wisdom to the dating process. With time and luck, you'll meet someone capable of doing the same.

Show Sources

SOURCES: "Dating Advice: Midlife Dating." "The Perks of Midlife Dating." Midlife Dating Network: "Dating Advice." "Guy's Eye View: Don't Do This on a First Date," and "The Very Best First Date Moves." New York Times: "Raising Awareness About AIDS and the Aging," "Facing Middleage With No Degree and No Wife," and "51% of Women Now Living Without Spouse." SeattleTimes: "Seniors Discover New Way to Connect: Online." Mera Granberg, writer, San Francisco. Jonathan Rosenfeld, PhD, clinical psychologist and associate professor, California Institute of Integrative Studies, San Francisco.

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