Dating After 50 For Dummies®

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Chapter 1

Jumping (Back) into the Dating Pool

In This Chapter

arrow Evaluating the state of your mind and body

arrow Knowing the best places to find dates

arrow Keeping safety in mind

arrow Saying and doing the right things in a relationship's early stages

arrow Talking about sex and money

When you haven't dated for a long time, dating again may seem so daunting that you don't want to approach the subject, much less start the process. But sooner or later, you feel a change in the way you think about various activities and daily life, and you know you'd like companionship or maybe a life partner. You also know that just waiting for the right person to show up hasn't been a successful strategy. At some point you realize that you need to tackle what it means to date again, and you start thinking about who you're looking for, where to look for potential dates, and what you have to do to prep yourself for dating.

Dating takes some rethinking of how you use your time and how you want to present yourself. Quite frankly, if you haven't dated recently, the rules of the road have changed, and you need some time to learn what they are. This book is meant to be a guide to dating — from renovating your dating skills and intuition to figuring out online dating to meeting people in new places. I also cover safety, which was probably not so important when you were in high school but is terribly important when you start meeting new people at this stage of your life.

Dating can be a lot of fun, and it's definitely a growth experience. Yes, it has its down moments and frustrations, but the upside is terrific. You can have a great romance, meet interesting people, learn a lot about yourself, and widen your horizons. Dating after age 50 (or at any age!) is worth the effort.

Getting Real: How Do You Feel about Yourself?

As you take on dating after some time out of the game, you need to evaluate your state of mind and body. I suggest that you work through some checklists to evaluate the emotional and physical state you're in now. This is ground zero because if you don't feel good about yourself, you'll transmit that feeling to everyone you meet, and it will undermine the possibilities that may have been there if you had come across as a self-confident person who is living a fulfilled life. You need to make sure that you can feel good about yourself before you even get fixed up, go online, or join a singles group.

Your psychological checklist

Chapter 2 contains some tools to help you review your state of mind, but in general, you have to attend to the following main aspects of your emotions:

  • Let go of past failures or frustrations and assume you can do better. You also need to let go of the hold on your soul that people you’ve loved or lived with still have. Your past relationship may have left you with shrapnel in your heart or a beloved spouse may have died and left you sad and lonely. Life deals people grave losses and traumas, and no one, least of all this author, minimizes these losses. The challenge is to put them in a place that allows you to approach someone new full of optimism and energy for exploring a relationship. If you’re not in emotional shape to do that, you have to work on your emotions until you’re ready to open up to someone new.
  • Get to a good place regarding your feelings about yourself. You’re older now and no longer have the face or shape of a 25-year-old. Of course, you know that rationally, but you have to find a way to feel good about who you are now. If you don’t like the way you look, you can either do something about it (exercise, lose weight, and so on) or accept the belief that you’re worth knowing — and desiring — just the way you are.
  • Surround yourself with people who are supportive of your new quest for love. If your children are unsupportive, tell them to get over their qualms and think about your needs as an individual. Hang out with friends who are happy for you and who send you back into the search for love if you start to back off. Everyone needs support, and you need to be willing to look for it and avoid naysayers.
  • Think about who you're looking for and why. You have much to consider now that you’re not building a family with someone or just starting out in life. Chapter 3 has a list of core characteristics that are important to consider for potential dates, but you need to take into account some differences at this stage of life. You may want to think more out of the box now that you aren’t picking the father or mother of your children. The person who was right for you in your 20s or 30s may not be a good fit in your 50s. On the other hand, you may still need someone who shares your values and fits into the culture of your family and friends. The bottom line is, before you go out again looking for love, you may want to revisit your romantic criteria.

Your physical checklist

You may be “camera ready” — or not. It's easy to get sloppy about your looks if no one is admiring you. Sometimes it's the little things people forget about (like clean nails!) that no one brings to their attention; others may look at those seemingly small imperfections, though, and make assumptions. Going out again requires giving yourself an honest once-over — or asking a supportive friend to do it for you. For example:

  • Hairstyle: Has yours been the same for the last 20 years? Maybe that’s not a good thing. Even men sometimes need a more stylish cut. Hair should look clean, neatly kept, and at the very least, not immediately aversive. And guys, most women find those comb-overs to hide bald or thinly covered areas unattractive. Consider an alternative.
  • Clothes: Clothes need to be clean and unrumpled. Wear something that doesn’t look like you slept in it or used it for a tablecloth. If you look like a mess when you meet someone, the person may never take the time to find out you can generally put yourself together very well.
  • Hygiene: Examine your fingernails, your breath, your body odor, and whether your hair looks dirty or greasy. It may be the end of the day, but you still need to look and smell fresh when you’re meeting a date. For some people, something as seemingly trivial as dirty nails can be a deal breaker.
  • Weight: Let’s face it: It’s a weight-conscious world. That doesn’t mean that no one will want you if you’re heavy, but it does mean that getting dates is easier if your weight reflects overall good health. Dating is a good motivator for setting up a healthy eating and exercise plan, which is invigorating, helps boost self-respect, and has health benefits. But don’t hesitate to begin dating just because you’re not at your best weight. Lots of people are in the same boat you’re in, looking for someone to love, and many will accept you just the way you are.

remember.eps It's not all about looks in the dating world, but your first interaction with someone is heavily influenced by appearances, so you need to pay attention to what you wear and your physical presence.

Looking in All the Right Places: Where to Find People

Dating for people over 50 used to be difficult. After you asked everyone you knew to fix you up, you still didn't have a clear path. These days, however, because of longer and healthier lives, cultural shifts, and online dating, meeting people isn't so difficult (although meeting the right person always takes a bit of time and resilience!). Chapter 5 gives you some clear directions about places that offer good possibilities to meet good people, but it all comes down to the five options I discuss in the following sections.

Events targeted at single people

Most cities have events that are specifically organized for single people. The nice part of these events or outings is that you're going to something you'd enjoy anyhow. It may be a bicycle trip, a wine tasting, a white-water rafting trip, or a series on foreign films, but the idea is that everyone who attends has a common interest, so you'll have something to talk about when you meet someone who interests you. At the very worst, you'll make new friends.

Public places

As you go about your day, you're constantly thrown together with new people, and some will be single and interesting. The hard part is getting to meet them because the only thing you have in common, to begin with, is being in the same place at the same time. That's why when you're at a grocery store or post office, or at the train station or an airport, you have to keep your eyes peeled. Consider all these places an opportunity, but you have to look for it and seize the moment by being inquisitive, friendly, and approachable (or approaching!).

Online dating

Online dating isn't for everyone, but it's where the people are. Millions of them, in fact. And the fastest-growing group among them is people over 50. That's why Chapter 6 is full of specifics about how to date online, because honestly, the choices are vast, and the chances of meeting someone you'd never meet any other way are high. Furthermore, online dating is the only way you can preselect a large pool of possible dates according to age, interests, and values. It's also the best place to go in terms of selecting people who are obviously interested in dating and available for a relationship (apart from the occasional jerk who's really married, but those people are the exception to the rule).

In Chapter 6 I go into detail about how to write profiles, select quality people, and learn the art of 20-minute coffee introductions. I don't call them dates; instead, these are really auditions, so you need to treat them as a kind of speed-dating experience, not real dating. Still, superficial as these first meetings may be, they eventually put two people who should be in front of each other together, and then real dating commences.


Younger people have parties all the time, but after 50, not so much. Still, parties, whether they're fundraisers, political get-togethers, or large office celebrations, are a good time to meet people you don't know. It takes a bit of guts to introduce yourself to someone you don't know at these large gatherings, and a naked fourth finger on the left hand doesn't always tell you whether someone is single. Still, it's worth going to these kinds of events because there are likely to be people there you don't already know.

Hobby-related activities

One of the best ways to meet people who share some of your passions is to meet them while you're engaging in said activity. That may mean skiing, going to an art opening, or taking an evening class on film, history, or anything else that you love. This way of meeting people is a long shot because there may not be any single people there besides yourself — or no single people who attract you — but if you do meet someone, it's a great way to begin a relationship.

tip.eps Try as many ways to meet people as you can. You never know which approach is going to pay off.

Making Your Safety a Priority

Unless you fall in love with the boy or girl next door, your coworker, or someone you've known for a long time, dating, almost by definition, is going out with someone you don't know. That means you need to be cautious about how you meet people, where you meet them, and what information you give them.

warning.eps I talk more about safety in Chapter 8, but in a nutshell, here are the five core aspects of safe dating:

  • Never give out your address until you've thoroughly checked someone out and are sure he's a safe person.
  • Never give out your home phone number until you're sure this is an emotionally stable person. A rejected person who’s unstable could start harassing you over the phone, and you may have to cancel your number, which is a pain in the neck.
  • Always do due diligence on the information your date gives you. You should be able to use the web to find out whether he has a criminal record, works where he says he works, is married, and so on.
  • Never let someone you've met for coffee or just a few dates walk you to your car. The chances of meeting someone who would push you into the car and kidnap you are extremely low, but not impossible.
  • Pay attention to early jealous behavior or compulsive calling or visiting. If it occurs, back away from the relationship immediately (but do it in a kind manner; you don’t want to stir up feelings of anger if you can help it).

Navigating First Dates and Beyond

In the early part of a relationship, you need to watch out for a number of pitfalls. I cover them in Chapter 7 and in other chapters in this book. The following sections outline some of the highlights.

Polishing your conversation skills

Starting a conversation with someone you barely know is always a bit awkward. It's hard to know what will lead to mutual interest. There are some graceful ways to get conversation flowing; here are some ideas:

  • Talk about things that interest your date. You really need to know how to talk to someone. If you’ve talked or read a profile already, bring up subjects you know this person is interested in. Make sure you get to cover something meaty.
  • Talk about a variety of subjects. Not all your sentences should start with “I,” and not all your stories should be about yourself. Pull out some subjects that contain both of your interests; for example, if your date is a chess player, and you are too, start talking about chess.
  • Be a good listener. When people are nervous, they have a tendency to either clam up or not know how to turn off a torrent of words.

    tip.eps One way to know you're listening is to ask the other person questions about herself.

  • Don't forget to use a little chemistry — after all, this is an interview for a date, not for a job. If you're attracted, show it, albeit in a subtle way. Hold eye contact, smile, and lean forward. Show you have emotions and sexuality.

    warning.eps It's one thing to show that you're attracted; it's another to come across as a lech or someone desperately trying to be a femme fatale. Avoid the extremes and just flirt a little, not a lot.

  • Avoid being controversial on this first meeting. You may have political differences, but there’s no reason to take them on immediately — unless that’s an extremely important aspect of how you choose someone to be in your life. Even then, you can find out someone’s opinion and state your own without getting into anything inflammatory. Raising the temperature at the table is exhausting and unnecessary. You also don’t want to close something down before you get a chance to know who this person is in other important realms of your life.
  • Whatever you do, leave your ex out of this. Talking about the person who deserted you, or whom you left, or who was the light of your life, is never a good idea.

    warning.eps It's easy to start talking about an ex even if you don't want to because your date may bring up her terrible divorce or breakup. Best thought: Nip it in the bud and change the topic. You'll be doing both of you a favor.

  • Save the bad news for later. No one needs to know your hospital record or your job problems when you’re just getting to know each other.

remember.eps This first date is still an interview, and you may not get another chance to talk to this person if it doesn't go well. So try to be your most interesting, warm, and compelling version of yourself. Have fun!

Being resilient

Probably the single most valuable characteristic you can have in dating is resilience. Sometimes you meet a lot of people, and none of them is right for you. You have to develop a nice way to tell people that they're not “the one” without being impolite or cruel. Harder is accepting that speech from someone else when you're really interested. But what can you do? Taste doesn't always match up. It's great when it does, and upsetting when you don't see why this person doesn't feel the same way you do, but the fact is, if he doesn't, then you have to move on.

Holding on to a “keeper”

The best part of a relationship happens when you're interested, the other person is interested, and you start to date. The stakes get higher, so you need to consider each escalation of the relationship so you don't do something that undermines this new connection. You need to do things to make this person value you and slowly ease into each other's lives (see Chapters 9 and 10 for more on this).

  • Create great dates. This is a time to be imaginative, to create fun or moving experiences that make you memorable. You should also open yourself up to new experiences because your date likely has something in her life that you haven't tried yet or don't know much about. Possibilities include a new sport or a class together that takes teamwork (tennis, cooking, and so on). Or perhaps you want to go exploring or even do something charitable that shows your date's depth as well as your own. (Chapters 9 and 19 give you additional ideas.)

    tip.eps Most cities have a city magazine or bulletin that lists special activities for the week. Look them over for great ideas.

  • Introduce your date to impressive and warm friends. You learn a lot about people from meeting and getting to know their close friends. Meeting your friends can make you seem all the more wonderful, and it also helps you see how your date would fit into your life if the relationship were to deepen.
  • Meet your date's friends and family . . . and win them over. Granted, it's not like meeting the family when you were 25, and the parents were the grown-ups. Now this entails your date's adult children and her friends who've lasted a lifetime. But these people have real influence and clout, which may or may not have been true in your youth. If you want this relationship to last, you want these people to like and trust you. (See Chapter 10 on how to make the first introductions successful.)

    warning.eps Don't introduce friends or meet family too soon. Get the relationship strong and grounded before you let in all these other opinions!

Moving into Tricky Territory: Sex and Intimacy

After you realize you have chemistry with someone, sexual contact usually isn't far behind. These days, given that you've probably been married (maybe even several times) or in a series of serious cohabitations, the expectation is that a serious relationship will include passion and sexuality. But people may have very different ideas about what sentiments should be in place before sex occurs. The following sections consider the usual themes that come up at this point (see Chapters 11 and 12 for more on sex and dating).

How long do we wait?

How long you wait before having sex is a personal issue. For some people, a few dates and a strong attraction is reason enough. In fact, many people have sexual intercourse or some kind of advanced sexual contact on the first real date.

Other people want to wait until they know what kind of relationship they're in and whether it's serious enough to qualify for sexual intimacy. More often than not, some kind of conversation about the relationship precedes sexual intercourse, but it's a great understatement to say that there's generally incomplete communication about sex and what it means.

How do we talk about it?

Obviously, if talking about when to have sex and what it means were easy, everyone would do it — and that's not the case by a long shot. Chapter 11 takes on this problem in some detail, but suffice it to say that you can have the conversation, and it can make you a better, more intimate couple. Talking about sex doesn't make it less passionate when it happens, but not talking about it may cause at least one partner enough worry and insecurity to impede sexual pleasure, create inhibitions, and obstruct emotional comfort.

So how do you begin? By being frank and direct. Literally say, “Before we have sex, I want to talk about issues that are important to me and also tell you things about myself that you need to know.” Some dates greatly appreciate this because they have issues to talk about too, and they don't want to shock you or disappoint you. For example, a man who has had prostate cancer and has a pump in his penis so that he can have erections needs to tell his dates that he has to pump up his penis to have intercourse. He can assure her that the experience will still be pleasurable for both of them. If he conveys this information in an unembarrassed and enthusiastic way, his date is likely to feel unembarrassed and enthusiastic, too.

tip.eps If you need to have this kind of intimate conversation about your body before having sex, do it at dinner or over a coffee or drink and not in bed. Your partner may not want to have sex, and navigating the situation in bed is way more difficult than making an agreement in a restaurant not to go forward.

What does sex say about the relationship?

Sex means different things to different people, and that's the problem. Some people think having sex means two things: that it's at least a serious dating relationship, and that it will now mean a monogamous commitment. This is a common understanding but hardly universally shared. If you think sex of any sort is a big deal, you definitely want to discuss what your entry-level standards are for creating a sexual connection. If you don't care what sex means (or don't care enough to have any difficult conversations), remember that it may mean something different to your partner and that the consequences of misunderstanding your date's expectations may be more than you want to handle.

What about monogamy?

One misunderstanding people have is about whether having sex with one person means not having sex with anyone else. To be clear, not everyone thinks that having sex is a promise of fidelity from then on. If you really care about monogamy — either from a health or an emotional perspective, or both — then have the conversation about the meaning of sex before you do it. Maybe sex won't happen then or ever, or maybe it will just happen later in the relationship, when you're both on the same page about what it means or entails. But at least there will be no regrets or accusations of feelings of betrayal.

What kinds of safety precautions are necessary?

Ideally, no act of sexual intercourse or oral sex should happen without a conversation about safe sex and the eventual use of a condom. Public health educators even recommend dental dams (thin pieces of latex that can cover the vaginal opening) because genital herpes can be transmitted by oral contact, and — rarely but possibly — the HPV virus that produces tooth decay can be transmitted.

Common practice, however, is much less ideal. Studies have shown that really low percentages of heterosexual men and women use condoms (gay men do much better). Chapter 12 talks more about this problem.

Talking about embarrassing issues

Other issues may be involved with sexual contact besides what it means about the relationship and whether it signals the beginning of monogamy. Older individuals can be painfully aware of how their bodies have changed and perhaps how they negotiate having disabilities caused by life-threatening illnesses such as cancer, heart problems, or diabetes, all of which can influence how their bodies look or whether they're orgasmic or able to have a full or automatic erection.

Bringing up such issues may actually be less awkward than you imagine. Most partners are sympathetic about these kinds of problems, and there are always ways to work around them that are easier if you broach the topic ahead of time (see Chapter 12). Many adults change their expectations of what a partner can and can't do as the decades pass by, and very few people expect their 50-plus partner to be a sexual athlete. Some are, but not the majority, and most people are ready to make all sorts of accommodations — and still enjoy each other tremendously!

Money These Days

Which is more awkward to talk about, sex or money? It's a tough call. Dating has changed (and continues to change), and it's never safe to assume what dating etiquette is when it comes to who pays for dating costs. Chapter 13 covers dating and money matters in depth.

Sharing costs

Though some men are traditional and would be offended to have a woman pay for a date, other men now want a 50-50 split. Traditional women are offended at the new deal, but feminism has reached men, and many believe that if women want to be equal partners, they need to be equal payers as well. If you're a woman who likes to pay your own way, this newer philosophy will be comfortable for you. If you're a woman who's used to male generosity, and you don't want to change the tradition, you have to look for a man with more traditional values.

remember.eps A 2013 study showed that the majority of men now want women to pick up the check at least occasionally.

Weighing the considerations of a fixed income versus a working income

One newer issue about money is between people who are still working full time and people who've retired. Retirement can bring new economic necessities that working people may not understand. The difference between partners’ incomes may not appear great in some cases, but it makes a big difference in how discretionary income is allotted.

You may find yourself in a situation where you like someone very much, but because one of you is working and the other isn't, certain kinds of vacations or expenses may not be possible unless one of you subsidizes the other. This level of largess requires rethinking gender roles. Even today, many women aren't used to being the one who pays for many luxuries or even just day-to-day expenses because men have traditionally had this role. But many of today's men are tired of paying the lion's share of expenses or simply can't do that anymore because they're on a fixed income.

remember.eps You have to decide what new accommodations you're willing to make to put a lifestyle together with someone who's not at the stage of work or retirement that you're in. You can take income or budgetary constraints into account when choosing your dates, but if that seems too coldblooded, at least make sure you check out the fundamentals early on, such as whether your date is retired or is earning a living that would work with your lifestyle. If money is an issue for you, it doesn't pay to ignore it when you're falling in love with someone.

Special Dating Strategies for Gays, Lesbians, and Bisexuals over 50

Much of what you read in this book applies to all daters, whether straight or gay. But some topics and differences are unique to people who are looking for a partner of the same sex. Chapter 16 looks at some of the issues that gay men and lesbians have to take into account. They include:

  • Finding people of your own age: All daters tend to want someone slightly or a lot younger than themselves. This seems to be true among gay men and lesbians, and it means that finding places that have people interested in their own age group is very important.
  • Finding people in places beyond bars or gay community centers: Bars seem to be great meeting places for younger gays or lesbians, but they don't work so well for older people. Also, gay men and women who congregate only or mainly in gay places are different from the ones who prefer mixed groups. Online dating has helped a lot of people 50 and older find age-mates, and in Chapter 16 I explore other places that may work well for gays and lesbians searching for a partner, including gay and lesbian sites on the Internet.

    tip.eps Political elections and affinity groups (like fellow mountain climbers) are great places to find partners if they're open and affirming about sexuality in general. If an election ballot has measures that affect gay people, you'll find many gay people working on the issue.

  • Negotiating monogamy: Unlike heterosexuals, the majority of gay men make no assumption that monogamy begins when sexually intimate dating begins. Though many gay men want monogamy (both for emotional and health reasons), a sizable number of men think that the core nature of male sexuality is non-monogamous. Gay sex expert and columnist Dan Savage has advised gay partners to be “monogamish,” which seems to mean that it’s good not to run around all the time, but on the other hand, you’ll probably be less disappointed in your partner or less frustrated yourself if you construct a relationship that allows for occasional outside sex.
  • Negotiating safe sex: Safe sex is incredibly important for gay men. AIDS is deadly and infectious, although it may respond well to treatments, when available. Gay men are very much at risk, so using a condom is critically important. Some men don’t want to use them; if that’s the case, the couple shouldn’t have penetrative oral or anal sex.
  • Overcoming your credibility problem if you're a female bisexual: “Straight by graduation” is a saying about young women who have romances with other women in college, meaning that women seem to have affairs in college with other women but drop the connection when they graduate and go into the real world. As a result of bisexuals having the “option” to go to their nonstigmatized heterosexual identity when it’s compelling to do so, lesbians tend to distrust self-described bisexuals. They don’t want to be dumped by a lover who suddenly or gradually begins to swing closer to the more “respectable” idea of being more centrally heterosexual.

Maintaining the Rest of Your Life while Dating

It's easy to lose track of your life when you're dating. It's so exciting to meet new people, and dating one or several people can start to take up all your discretionary time. But don't let that happen, even when you're overcome with passion and have a real crush on someone. You need your friends and family in the long run for advice and friendship, and that means sharing a date with them early on. In Chapter 10 I go over timing a first introduction to someone you're steadily dating. You want to make sure it's not too early or too late. It's too early if you don't know how you feel about this person, and therefore, you don't know how to introduce the person to your friends or family. It's too late if your date is a mystery to everyone who knows you, and the people who are close to you start to feel left out of an important part of your life.

Another advantage to an earlier rather than later introduction is that you'll learn a lot about how your date fits in and also get early input from your friends and family. You want to be careful and not get over-influenced by either positive reinforcement (“Don't let this one get away!”) or negative reaction (“Isn't she a little short for you?”). You want advice but not a cacophony of opinions and directives. This means you have to look at your friends somewhat differently and decide whose advice really matters.

Most of all, you want to test the waters to see whether you can fit your date into your life (and whether you can fit into her weekly routine). Practicalities are important. There's love, and then there's “fit,” and you want to make sure you have both!