10 Pieces of Retiree Dating Advice

By: Terri Briseno

You're never too old to date. See more healthy aging pictures.
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In May 2011, the oldest couple in history to tie the knot entered into married life. Their story offers a lot in the way of dating advice for retirees, whether looking to date casually or to find the "marrying kind." The newlyweds, Californians Rose Pollard Lunsway and Forrest Lunsway, both widowed, found love on a blind date at a dance after each having lived long and varied lives. The bride thought that she would never marry again, but vowed she'd marry her man when he turned 100. Her boyfriend courted his wife-to-be while living 40-miles apart and dating for 30 years. His 90-years-young bride kept her promise and said "I do" on his centennial birthday [source: Coffey].

While this may not be "proof" that you really can find love at any age, it is a true story of blind dating, widowhood, being unsure of remarriage and enjoying each other while taking it slow.


You might be looking for love and not finding it, but embracing all of the "likes" along the way is truly the stuff of life "right now." It can be difficult and sometimes even a lot easier to stay home or stay as you are -- especially after a bad dating experience or two -- but it can get better. Maybe you're not even looking for love but are looking to date for fellowship and companionship to enhance your single life, and that can be a long and happy road, too.

Whatever your reason, whether it is the loss of a spouse, lifelong singlehood or divorce, retiree dating is a lot like younger dating: You can probably benefit from a pointer or two.

10: Be Open Minded

If you're ready to enter or re-enter the dating world, or if you're looking to increase your already active dating life, are you seeing endless possibilities or few options? Dating has lost its "sitting home by the phone" and quaint but out-dated formality, and maybe it's time to reconsider your options.

Perhaps it's been a long time since you've "played the field," so being open to the less formal advances of today's dating dance may take some getting used to. It's fine to be casual and friendly with the opposite sex and test the waters. Taking a chance on small talk with someone who interests you might not lead you to "the one," but that sting of rejection is almost always fleeting. The more you try approaching others, the easier it gets to let the "nos" go and the "yeses" flow into easy conversation or a planned meeting. Most likely, it's the chance not taken that will linger in your memory much longer.


Another chance to show your openness to new dating possibilities is to start accepting offers from friends and family who "know a nice retired gentleman in my building" or "work with the sweetest widow in my office." Even if your loved ones are pushing matchmaking with people you aren't connecting with, there are always stories of long-lasting, head-over-heels in-love meetings that weren't supposed to work out, as well as fantastic friendships that started on dates where there was no chemistry but lots of fun. Who knows, a setup may be a let down, but some bad dates can lead to great friendships.

9: Share Life, Not Loss

Let the people you meet get to know you -- not just the you attached to loss or loneliness.
Let the people you meet get to know you -- not just the you attached to loss or loneliness.

After a long relationship, or even long singlehood, it can be difficult to separate the past from the present. Dating again or for the first time after a long period of mourning or healing is less about talking about the person you were with previously and more about letting the people you meet know you -- not just the you attached to loss or loneliness.

Get to know each person you date in the present and keep talk about the past focused on individual histories or the basic and positive things about your family life without a lot of "we used to," "my wife and I" or "all those years alone." If a relationship takes off there is plenty of time for sharing hurts and difficulties later with more intimacy and the tenderness that comes over time. Studies have even shown that what both men and women least like about dating is meeting people who focus on the past "baggage" of their lives on a date [source: Montenegro].


If after a number of dates you find that you can't separate yourself from your past and loss, it may not be the best time to date [source: Schwartz]. Maybe it's time to talk with a counselor and get to the root of who you are first, though it may just be a matter of practicing conversation with friends who will let you know when you're spending too much time looking back [source: Schwartz].

8: Involve Family and Friends

Sure, it's nobody's business what you do with your life as a grown man or woman, but are you sure you want to go it alone, just you and the "dating world?" Loved ones not only worry and tend to give unwanted -- though sometimes very good -- advice, they also love you and love sharing life with you. Getting feedback about potential dates and sharing the adventure of meeting and planning an outing with someone new is something to get excited about, and most people close to you will share in your excitement. Let them support you while you learn to filter the unsolicited advice from time to time.

Although we've all had to acknowledge "My mother was right," or "My buddy knew exactly what was coming" after falling on our faces or just spending a couple of hours that could have been avoided if we'd listened, it's never too late to accept advice and take what you will. It's really not much different than dating as a teenager or young adult: Those closest to you can discern things about people that you may not see yourself. Keep them in the loop.


It's also important at the very least to let someone know the "who, what, where and when" of a date for safety reasons. Make your schedule an open book when it comes to meeting with dates so friends and family can be assured that you're safe.

7: Dress Appropriately

Caring about your appearance is as important for your own self-esteem as it is for the impression you can make.
Caring about your appearance is as important for your own self-esteem as it is for the impression you can make.
Digital Vision/Ryan McVay/Thinkstock

There's an unofficial "maturing" of style as we get older and comfort starts to reign over fashion, but dating at 80 or 18 can mean enjoying the prepping as much as the pairing up. It's very important to feel comfortable on a date and to dress in a way that reflects who you are, but leave the in-house clothes in the house. Worn-out sweat suits and housecoat dresses aren't date attire until you know your date well enough to really get comfy watching a movie on the couch. Wearing the broken-in clothes you love will make you comfortable, but on a date, it's doubtful that they'll make you feel confident and at your best.

Caring about your appearance from head-to-toe is as important for your own self-esteem as it is for the impression you can make on someone of the opposite sex. It can be tempting to try really hard to look young or sexy or sporty or even very formal, but keeping it simple will help you keep the focus on how you feel and who you're with rather than on what you're wearing and how much you need to tug, adjust and suck-it-in to keep it in place. Too much of a good thing on the outside can distract from all of the great stuff on the inside, and too casual or unkempt a look will have the same effect, but with the added assumption that you didn't care enough about the person you're meeting to impress a little, too. Remember getting ready for Friday and Saturday nights in your early decades? Re-create that getting-ready ritual for added anticipation of a date.


6: Go Online

Young people seem to be the forerunners in anything computer-related, but some recent studies show that people aged 74 and older are using social networking sites more and at a faster growing rate than any other age group [source: Shellenbarger]. Spending time online to chat with friends and share photos with kids and grandkids is one thing, but cyber-mingling on dating sites is another. A growing number of retirees have the technical know-how to blog, post, tweet and surf, but meeting people online still means using some non-technical language and methods: finding, introducing, flirting and asking out or "breaking up."

Online dating sites offer incredible opportunities for seeking out likeminded people without leaving home, and with age-specific, religion-specific and interest-specific options for searching, it's easier to narrow down the playing field, so to speak. Knowing why you're on the sites in the first place and letting others know what you're looking for is a good start. Some online connections are solely for long-distance friendships online, while others are centered in finding a long-term mate or casual dates for companionship. Being honest from the start about who you are, how you want to connect and what you look like will save you and other people lots of time and heartbreak. Being aware that not everyone will be honest is also important to remember!


If you do start finding men or women you'd like to meet in person, talk on the phone before meeting. Communications over e-mail and text are inadequate ways to really know someone, so try mixing up writing with phone calls to get a better sense of whether you're connecting well enough from a distance to close the gap.

5: Go Slow

Have you ever been so busy with an activity, whether volunteering on a board or being on a bowling team, that when you finally slowed down or stopped doing it you realized you didn't really enjoy the activity itself? Dating can lead to the same kind of busyness with mediocre results. When you find that niche or just right match for your interest and skills as a volunteer, for example, you absolutely love what you do and why you're doing it. Staying busy on dates and moving from one activity to the next keeps you from getting to know one another and whether you really like each other or just like each others' company while staying busy.

Taking your time and planning first dates that focus on conversation might not be as exciting as musical theater followed by club dancing or eating in a popular but crowded and noisy restaurant before seeing a movie, but it will reveal more about who you're with. Nerves can keep early conversations stilted or centered in small talk, so keeping first dates short and simple works well. Having coffee or dessert and building up to a long walk or a couple of hours in a bookstore sharing reading likes and dislikes, for example, will open or close the door to more active dates later.


4: Be Safe

There are snakes and scammers, scoundrels and con artists lying in wait for their next victims of any age, but often retirees are the target of schemes because of their net worth and their vulnerability [source: FBI]. Beware of any interaction that just doesn't feel right. Even the smallest red flag about a person's character or intentions is worth taking a step back and asking for second and third opinions from friends and family. Beware of romantic interests who seem too eager to know everything about you or to share everything with you early on. It may be a forced and false intimacy in order to gain access to personal information. Sharing details of your life verbally gives access to details of what you have stored up in savings or in possessions, and letting someone into your home can give access to vital paper records and even electronic files with personal data.

Guard your information and your secrets until you're certain of their character and background. Feelings often lie, but criminal records or missing gaps in a person's story are very telling. Never share passwords or physical keys or give money for businesses or to help someone out unless you're absolutely sure of who a person is and how they will use your money. Safeguard what you've earned and worked so hard to attain, and use wisdom -- yours and that of personal and professional counsel -- in getting to know someone before you let them get too close.


3: Be Yourself

Somehow "reinvent yourself" has become one of the mottos for the later stages of life, and it can be a time to do new things and know yourself outside of decades of work and parenting life. Reinventing doesn't have to mean becoming some kind of "newer" and "better" or "more exciting" person, though. It can be about doing what you want based on being who you are apart from being a worker, head of household, or mother and caregiver.

Despite the statistics about the shrinking pool of available men and marrying women over 65, approaching dating as if there are plenty of fish in the sea isn't a bad idea [source: Brody]. Don't try to fit someone else's mold but trust your instincts about whether you are a good fit for the person or just a likeness and a project that would need to change and accommodate in order to satisfy a relationship.


A 2003 study of midlife singles found that the top two reasons for dating were to have someone to talk to and do things with and "to simply have fun" [source: Montenegro]. Being yourself, the same person you are at home with friends as you are out on dates, will lead to more fun for both people on a date. Trust your instincts, and if the man or woman you meet doesn't seem to like who you are, keep looking until you find someone who does.

2: Join Groups

Most TV sitcoms have an episode or three devoted to the hapless misadventures of guys or girls trying to impress or "find themselves." They sign up for different art classes or sports and clubs and play the fool until they have an "aha" moment. A lot of older people either know what they like or are set in a pattern of doing things just because they do them without really knowing what they like. Shaking things up and being the hapless explorer isn't such a bad idea if it leads to finding a passion and people with common interests. It's also a great way to break the ice when an activity or group just isn't "your thing."

Social clubs, fitness classes, health and wellness sessions, and community meet-ups are generally safe and fun ways to meet other retired singles. Finding a club based on an old interest or a new one, such as cooking or playing bridge, and taking exercise classes beyond the usual, maybe yoga or boxing, are a couple of ways to connect. Volunteering in the community or at a local church or nonprofit can help you find like-minded or even like-hearted people to serve alongside while serving others.


Do what you know you like and try what you think you might like and you could find your niche, as well as a possible match.

1: Have Fun!

Uncontrollable laughter and embarrassing moments are all part of dating at any age.
Uncontrollable laughter and embarrassing moments are all part of dating at any age.
Brand X Pictures/Thinkstock

Retirees have a leg up on everyone else when it comes to learning to put things in perspective, and usually that includes the ability to laugh at themselves. If you are a dating retiree or are ready to take the leap of faith and go out on dates, you've experienced more than most of the younger generations, and if you haven't "seen it all," you've seen enough to take a good or bad date in stride.

Awkwardness, uncontrollable laughter and embarrassing moments are all part of dating at any age. Being ready to NOT act your age and to feel like a kid again when there's chemistry and intimacy is an even better part of dating, young or old.

Have fun and be ready to laugh at or even during absolutely bad dates while enjoying the differences of two people who don't match but can make the best of it. And the good dates? As toe-curling as ever.

Lots More Information

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More Great Links

  • Baker, Molly. "OMG! My Grandparents Are My BFF!" The Wall Street Journal. May 9, 2011. (May 8, 2011)http://online.wsj.com/article/SB10001424052748703280904576247152267875970.html?mod=googlenews_wsj
  • Brody, Jane. "Getting on With Life After a Partner Dies." The New York Times. June 10, 2010. (May 6, 2011)http://www.nytimes.com/2010/06/15/health/15brod.html?ref=health
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