Falling In Love Again:The Single Boomer’s Guide to Dating

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Falling In Love Again:

The Single Boomer’s Guide to Dating

Falling In Love Again

Table of Contents

Introduction                                3

Part I: Attitude                            3

You Come First                            4

Don’t Gender Bash                       4

Don’t Stay With Energy Drainers    5

Learn to Say No                          6

Accept Yourself                           6

Learn to Flirt                               7

Stop Making Excuses                   7

Be the Date You Want to Have      8

Part II: Where to Meet Someone   8

The Gym                                    8

Stores                                       9

Classes                                      10

The Dog Park                              10

Traveling                                    11

Speed Dating                              12

Online                                        12

Conclusion                                  13


There’s an old saying that “your attitude determines your altitude.”  If you want to be successful at dating after you’ve been out of the dating pool for a while, you need to develop a winning attitude first of all.

Dating after 45 is different from dating when you were 20.  You’ve changed.  The men or women in your dating pool have changed.  And, the environment in which you are dating has changed.

This report is divided into two sections.  The first deals with your proper dating attitude.  The second talks about 7 great places to meet members of the opposite sex when the bar scene is no longer an option.

Part I: Boomer Dating Attitude

Kathy was newly separated from Jim, her husband of 29 years.  She hadn’t been in the dating pool since she was 23.  Now 52, she still had a lot of good years ahead of her and she knew she didn’t want to spend them alone.  But she didn’t know how to put herself back on the market either.

Wes, age 61, lost his wife Marie three years ago to breast cancer.  He had a long grieving process but he too doesn’t want to be single anymore.  He doesn’t want to betray Marie’s memory, but he knows that pining away for the rest of his life isn’t the solution either.

Are you wading around in the dating pool? Are you clueless of what the new rules are and bogged down with fear? Hesitating because the dating game has changed dramatically since you were in your 20s? Sooner or later – if you truly desire a relationship – you must jump in. Make a big splash. When you decide that you are ready to play the dating game, look at it as an adventure.

The grown-up dating game has never been more interesting and challenging. There are more players than ever before. Why? Because of higher divorce rates, longer life spans, and a greater tendency to never marry. This contributes to more single Americans than at any other time in our country’s history.

The U.S. Census Bureau tells us that of the 97 million Americans who are 45 or older, almost 40 percent – 36.2 million – are available singles.  That means that if you are on the market, there are plenty of available mates.

You Come First

The most important thing you can do to further your dating potential is to take care of yourself.  When you learn what you need to be fulfilled as an individual, you make yourself more attractive to a partner.

There are two dimensions to this.

The first is to examine who you are and what you want in a partner.  Use self help books or even see a counselor to help you focus on who you are and what you want.

The second dimension is to take care of yourself physically.  Remember that the opposite sex is going to judge the book by the cover first in most cases.  But, you will also feel more confident when approaching men or women when you feel good about your body.  Eat right, exercise, and pamper yourself.

After his divorce, Ken didn’t jump right back into the dating pool.  He decided to give himself a break.  He started jogging again every day and turned to a lacto-ovo-vegetarian eating style.

He also attended a few seminars on positive thinking.

All of this physical and mental recharging put him into the right frame of mind when he started back on the dating scene.

That’s why he was thrilled to meet Camryn on just his third blind date.  Because he was in the proper frame of mind, he was able to make a love connection with someone who had the same mindset.

Don’t Gender Bash

Many boomers are back on the dating market because of a divorce.  This can lead to gender bashing.  If you think that the opposite sex “did you wrong,” you will have trouble attracting them!

Phil’s first wife left him for another man when he was 34.  He remarried when he was 37, but after 15 years of marriage, his second wife wanted to “find herself.”

Phil didn’t know if he could ever trust any woman again after these two failed marriages.

His first forays into the dating world were disasters.  On one early date, when a woman announced that she had initiated the divorce against her husband, Phil got up and left the restaurant immediately.

Before he was able to get into a long term relationship, he had to deal with the bitterness and hostility he had toward women because two women had hurt him.  These views were keeping him immobilized.  He wasn’t able to have fun as a single person as a result.

Phil finally went to a counselor to work through the issues because they were quite strong.

Not everyone will need to seek professional help, but if you find yourself thinking about how “my wife took me to the cleaners” or how “he left me for a 20 year old bimbo,” you need to clear yourself of these thoughts before you will have any success in dating.

Don’t Stay With People Who Drain You of Your Energy

Part of the beauty of dating after your prime reproductive years is that there’s no pressure to “settle down” or just “settle” right away.  If you hook up with someone who drains you of your energy, move on.

Karen was a lively 50.  She met Darryl at church and it seemed that everything was going well on their first few dates.

Then Darryl started talking about how his boss kept him down, how his mother favored his brother all of his life, and how he resented the fact that he had never been able to complete his college education.

After a couple of months, Karen began to dread going on the dates.  A friend pointed out to Karen that she had become increasingly negative herself.

Karen realized that she didn’t need Darryl’s baggage.  She wanted a sunny, positive man in her life and she was willing to date other people until she found one.

Avoid contact with people who drain you of your life-giving energy.

Learn to Say “No”

When you were two, you said the word “no” a lot.  There is a good reason for that.  Saying “no” is an act of autonomy.  Just as a two year old is trying to make herself distinct from her parents by saying this, when you say no to people or situations that don’t fit, you are making yourself autonomous.

Brynn had been a people pleaser all of her life.  Most of her friends thought she had been a doormat in her relationship with Scott.  It didn’t really surprise them when Scott divorced her.  But it did surprise Brynn.

When she finally got back onto the dating scene, she felt that she had to say “yes” to any man who came along.  Her lifetime feelings of low self worth were destroying any chance of meeting someone who would be good for her.

At a friend’s suggestion, Brynn joined a women’s empowerment group.  She felt like she was back in the early ‘70s, but because she couldn’t say no to the friend, she went every Wednesday evening.

Surprisingly, this time, it was great that she said “yes” because the group taught her to say “no.”  After that, she could be more selective about the men she dated and take more control of the relationships she was in.

She soon met Lou and sixteen months later, they were married.

Accept Yourself

Nancy realized that she had “less to lose” when she entered the dating world again at age 62.  She wasn’t looking at a “lifetime” of love, she simply wanted it right now.  She also felt that she had less to learn the hard way.  She wasn’t an insecure 22 year old anymore.  She had a lifetime of experience behind her.

Nancy realized that she wouldn’t always do everything right, but that nobody really cared.  She decided that she wouldn’t make any more excuses about who she was and what she had done.

By saying “I am here and I am glad and proud to be who I am,” she was able to attract a good number of men.  After all, confidence is sexy!

Learn to Flirt

Marilyn was in just the opposite situation.  She was a confident, in your face woman.  When she ventured back out into the dating world, one of the first things she realized was that she had to learn to flirt.
Effective flirting is simply a way to let people know that you noticed them and want to get to know them. Nothing more and nothing less. Keep it light and keep it fun. The most effective flirting always includes a smile and eye contact.

Flirting is a fun activity that everyone should engage in from time to time and thoroughly enjoy. When you take the fun out of flirting, it becomes a high-stress situation that has nothing to do with enjoying yourself. Keep it low pressure, just like dating. Flirting should be all fun and games.

Flirting shouldn’t be taken too seriously.  It should be an invitation to another person to open up dialogue.

Some of the ways to flirt include:

  • Smiling
  • Making eye contact for just a few seconds
  • Shyly avoiding eye contact
  • Playing with your hair
  • Licking your lips
  • Using body language such as a touch on the arm to communicate interest

Stop Making Excuses for Not Going Out

What are the things you tell yourself to keep from going out?  Some of the typical excuses include:

  • I’m too busy.
  • I am waiting for the right person.
  • The good ones are all married.
  • All men/women are jerks.
  • I can’t do this to the children.
  • They’re all losers.
  • It’s going to be a disaster.
  • I’m not ready.
  • No one will like me.
  • I’ve been hurt too many times before.

It’s not easy to get back out there.  But once you try, it does become easier.  You will be amazed at the wonderful world that will open when you actually step into it.  And one thing you will find is … yourself.

You might not always be right, but then, who cares?

Be the Date You Want to Have

When you start to go out again, think about what you want in a date – and then reflect that in your own behavior.  Would you like to date an interesting person?  The be interesting.  Do you want someone to listen?  Then you should listen.

Always be honest about who you are.  You don’t have to like the same things as your date does.  In fact, your experiences and interests actually make you more attractive.

You should always smile when you are on a date.  Laugh a lot.  Before you go on a date, think about things that are funny in books you’ve read or movies you’ve seen lately.  This will  make you a more interesting date.  It will also make you happy which will reflect in the evening out.

Part II: Where to Meet a Fellow Boomer

When you were 17, your dates probably came from your high school.  In young adulthood, there were social settings that attracted singles including bars and college organizations.  But where does a boomer find fellow boomers to date?

Here are seven ideas about where you can find singles over 45.

The Gym

Boomers are not ageing gracefully.  They are staying fit by exercising and eating well.  So, what better way to meet someone new that to go to the gym.

While it is awkward to strike up a conversation with the person running at 10 miles an hour on the treadmill next to you, a good solution is to join a co-ed fitness class.

Men are more likely to meet women in an aerobics or yoga class whereas women are more likely to meet men in high impact or martial arts based classes.

Men typically compliment women as an introduction line.  But at they gym, they shouldn’t comment on physical appearance.  Instead, comment on her abilities.  This shows you are a nice guy that notices things and also that you are not just focused on her looks.

Another thing you can do is take an extra bottle of cold water with you.  If you see someone who is attractive and who is thirsty, you have a natural opportunity to strike up a conversation.

Once you do get friendly with someone, suggest an active date such as hiking rather than a more sedate one like dinner and a movie.  An active date will let you get to know someone better than if you were sitting in a dark theater.


There are a number of types of stores that lend themselves to meeting people.

Bookstores are one.  When you see someone browsing the aisles at a bookstore, you have an instant insight into what kinds of things they are interested in.  If they’re in the business section, they are interested in selling things.  In the literature aisle?  They’re probably literate.  The computer section will attract techies.

Many bookstores have cafes now.  If you meet someone you find interesting, you can go and grab a cup of coffee and chat.  It’s a low pressure way to have an instant “date.”

Another type of store that gives you insight into what another person is interested in is a music store.  Music is essential to most people.  You will know what kind of person one is by the music he or she listens to.

Many music stores now have headsets where people can listen to the music.  If you find someone listening to a song, ask them what they think of it.  This might lead to further conversation.

Charlene had a small electrical issue that she thought she could handle herself.  She went to Home Depot to see if she could get the right part.  But, she was soon overwhelmed with the choices.  Randy came to her aid and got her squared away.  They chatted for a few minutes and decided to go get coffee at the Starbucks across the street.  That led to a few dates.

Eventually, Charlene and Randy fizzled out, but Charlene thought it was a great pick up place.  Now, when she wants a date, she goes and buys light bulbs or something like that at Home Depot.  About one time in three, she meets an eligible man.


Just like classes brought people of similar ages and interests together in high school and college, special interest classes can bring boomers together.

There are many types of classes available.  The Osher Foundation recently disbursed millions of dollars to colleges across the nation for the purpose of developing non-credit continuing education classes for older adults.  These classes range from writing to philosophy to current events.

There are also independent classes.  Art classes, writing groups, and cooking classes all attract adults who want to better themselves.

Mark and Theresa met in a wine class.  They both enjoyed drinking wine but neither knew enough to even call themselves amateur sommelier.  When they started the class, neither Mark nor Theresa were doing it with the intention of meeting someone.  But, they were immediately attracted to each other and the material of the class gave them a common bond for talking outside of class.

Dog Park

Most cities now have dog parks.  If you have a pooch, consider taking him to the dog park rather than a walk around the block.

Dog parks attract people who have a common interest in their pets.  Most people go to the park around the same time each day and stay for 45 minutes to an hour.

Tom started taking his Labradoodle, Ralphie, to the dog park after he broke a toe and found taking him on his walk every day too painful.  Letting Ralphie romp around with the other dogs let him get the exercise he needed.

But what really surprised Tom was how much he enjoyed meeting the other people at the park.  He started going around 3 p.m. every day and met a core group of people who showed up around that time.  They were soon inviting him to pot lucks, barbeques, and even dinners out.

He soon found himself talking to Sue, both at the park and at the social events.  After a while, he asked her out and she was quite happy to go.  The dog park had been the forum for their introduction.


Many singles don’t like to travel alone.  For one thing, travel is an experience and it is more fun to share.  But, singles pay a premium to stay alone in a hotel room.

That’s why many singles prefer to travel on singles trips.  50plus Expeditions offers adventure oriented travel for active travelers over 50.  There’s no mandatory single supplement so each tour attracts a number of singles.

They take travelers to the Antarctic, Africa, Asia, Europe, and Latin America.

There are also a number of cruises that feature special 45+ single’s events.  CruisingForLove.com is a site dedicated to listing all of the single’s cruising events and they make special note of the events designed for older adults.

Jim and his brother Keith went on a single’s cruise right after Jim’s divorce.  Keith, who had been single for some time, had been on these excursions many times.  Jim was initially nervous about the experience.  He didn’t think he was ready to meet someone yet.

But, he met Bobbi at the mixer on the first night.  They spent the rest of their 7 day Caribbean cruise in each other’s company.  After they got back to port, they had to go back to their separate hometowns, but they keep in touch.  They’re considering going on another cruise this winter just to repeat the experience.  And this time, they won’t be going with a group.

Over 50 Speed Dating

Speed dating is something that didn’t exist when boomers were in their earlier dating years.  The concept was developed in the Jewish community to introduce Jewish singles to each other.  But it has caught on in the larger singles world as well.

The way speed dating works is that a roughly equal number of men and women are invited to participate in an evening of short “dates.”

The women stay at their own table.  The men move from table to table throughout the evening on a set schedule.

So, each couple gets to meet each other for three to seven minutes.  They talk during this time to see if there is any kind of love connection.

At the end of the evening, everyone “marks their cards” as to who they would like to talk to again.  Then, where there is a match with both the man and the woman selecting each other, their names and phone numbers are passed on.

There are a number of companies running such dating services.


Perhaps the biggest change in the single’s scene between the time you were 20 and now is the invention of the internet.  You can now go online and find the man or woman of your dreams.

More than 23 million single Baby Boomers have used online dating sites.  If you are inclined to go to the internet for love, you are not alone.

You can start on a large free site.  As you get comfortable with the medium, you might find yourself drawn to a more specialized paid site where your choices are more refined and you spend less time viewing profiles that don’t match your interests.

When you start on an internet dating site, you will fill out a profile.  On some sites, this is merely a few questions regarding your vital statistics.  You may also have an opportunity to write a short (100 to 250 word) description of yourself and what you are looking for in a date.

Then, you will have the option to upload a photo (or sometimes a video too) of yourself.  You should be prepared to upload the photo because other singles searching the site almost always require that their search results show only those profiles with pictures.

At this point, you sit back and see if you get any responses.

Usually you have to upgrade to a paid membership if you want to respond to messages or to initiate contact with someone who looks interesting

The largest internet dating sites include Match.com and eHarmony.com.  You may want to consider specialty dating sites like TrekPassions.com (sci fi and Star Trek fans), WineLoversMatch.com, or DogLoversPersonals.com.  Or, you can look for sites geared just for your age group.  PrimeSingles.com and SinglesOver50.com are two examples.


If you are heading back into the dating world after a long break, it can be intimidating at first.  You may feel that you are rusty at it.  You may also have lost your confidence.

You probably don’t have the same body that you had when you were 20.  Your face may have lines.  Your butt may sag.

But that doesn’t mean you are any less attractive.

Even if you don’t connect right away, that’s okay.  Consider your first dates to be “trial runs.”  You don’t have to “close the deal” right out of the gate.

Remember that boomer dating is not about finding the person that you are going to raise your children with.  It’s about loving someone right here and right now.

Relax.  It’s not forever.  It’s just a date!

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