Striving for that Sunset Romance: Tips for Single Seniors


Dating in your senior years can seem, at first blush, silly or even awkward. If you are widowed or divorced, though, there’s no reason why your age should keep you from kindling a new romance and finding someone to share your sunset years with.

If you’re thinking about it, though, you may not know where to start. We talked with six dating and relationship counselors to get their tips and advice especially for seniors re-entering the dating scene.

First Things First

Tips for single seniorsLet us be the first to welcome you back to the proverbial sea. It’s normal to be nervous, and if you’re worried that a lot has changed since the last time you dated, you’re probably right. The important things, however, have not changed, and the life experience you have accumulated over the decades should put you in a place of calm confidence within the dating scene.

Stephanie D. McKenzie, MBA and Coaching Director at The Relationship Firm, is a personal and relationship counselor, and author of The Business of Dating.

Stephanie McKenzieUnderstand that every experience has made you who you are today. Explore your innermost self, and extract the parts of you that are filled with joy and peace. Strive to be that person every day. – Stephanie McKenzie

Kimberly Seltzer is the therapist, image expert, and dating coach behind Elite Image Makeovers. She utilizes a unique combination of therapy, in-field date coaching, and styling to help people with their confidence and dating life, and agrees that you should start with you.

Kimberly SeltzerThe first step is to get back to the basics by figuring out what your passions are, and really getting in touch with your true self. Dating can be overwhelming, so focus on you first. After being in a long term relationship, people tend to stop doing what they used to love. Revisit the things that once inspired you, and get involved again. Perhaps there are hobbies, places to travel, or extracurricular activities that you’ve been wanting to do. Reconnecting with your passions will help you find the things that make you happy, focus on yourself, and even meet other like-minded single people. – Kimberly Seltzer

Deanna Cobden, of Dateworks, knows the modern dating scene, and has a passion for helping others understand relationships and master the art of attracting the opposite sex. As a certified dating coach, her experience, education, and personalized service come together to get results for her clients, making them as attractive and successful as possible.

Deanna CobdenRealize that it’s okay to move on, try new things, and reinvent yourself. Let family members know how you’re feeling and why it’s important for you to date and find a partner to enjoy life with. The key to making dating again fun is to branch out and try something new, or date someone you wouldn’t normally consider your type. – Deanna Cobden

Start with you, and give yourself permission to try something new. You might make a silly mistake along the way, but better that than regretting what you were too afraid to try!

Meeting People

love at first clickIt might seem difficult to branch out and meet new people, especially if you’ve had a significant other for most of your life and your friends haven’t changed in years. Don’t let that deter you! There are plenty of ways — new and old — for you to go out and meet someone interesting.

Laurie Davis is the CEO and Founder of eFlirt Expert, a personal branding service that helps singles navigate the digital dating world and create lasting relationships. She authored the best-selling book, Love At First Click: The Ultimate Guide to Online Dating, and her online dating advice has been featured in more than 500 international media outlets.

Laurie DavisThere is a huge learning curve not only for navigating the dating site and adjusting to what it’s like to see a match on virtual paper first rather than face-to-face, but also understanding how best to communicate on the platform. For example, transitioning the language from a professional tone to a flirtatious one is something [people] struggle with. Also, courtship has completely changed. The social norms have shifted by way of dating practices — from dinner dates to drinks, for example — and with modern-day dating it’s common to date multiple people at once. In fact, if you’re online dating this is a must, because you can’t send one email at a time. There is no assurance the other person will reply, or when they might respond if they do. When you’re messaging multiple people, it often turns into multiple dates — Laurie Davis

Damona Hoffman coaches online and offline dating through her Dates And Mates brand. She started by teaching actors about auditioning and personal branding, and that experience has helped her create a unique strategy that now helps people find their perfect match. If you’re not comfortable with online dating just yet, try special events for meeting people in the real world.

Damona HoffmanJoin a meetup group that is based around an activity that you love. It’s easier than a general singles mixer because you are there for a shared interest and not only for dating. Maybe you’ve considered asking friends for setups or going to the singles events at your church, but you’ve been too shy to do it. Give yourself a challenge to do something new and see what happens. – Damona Hoffman

Gary Gunn is the founder of the Social Attraction Academy and author of the “An Education In Dating” series. He specialises in coaching single men and women how to attract their ideal long term partner, and he emphasizes meeting people around shared interests.

Gary GunnExperience has also taught us that we are never really too old to take up a new hobby or something that we are passionate about. The key, really, is to do what we love, but to make sure that we talk and communicate with other men and women at the events so we can start to increase our social circles. – Gary Gunn

Cobden also recommends that everyone should, “make chatting with people a part of your everyday life so that saying ‘Hello’ becomes normal, not awkward.” If you’re going to start dating again later in life, it is important to talk to new people and stretch your social circles — online or off — to find the right person for you.

A Night Out

If it has been a while since your last date, nerves are normal. What do you wear? How do you act? Ultimately, be true to yourself, but it helps to have some expert advice too.

What To Wear

It’s okay to take a little time to check out your wardrobe.

While it sounds shallow, take time to put your look together. Just because you’ve aged, doesn’t mean that you can’t be stunningly beautiful or handsome. Taking the time to create a new look (or refresh your old one) is not only going to make you look better, but it will impact your confidence. – Stephanie McKenzie

Ladies, fashioning your look around your new body doesn’t mean sacrificing style or femininity.

As we get older women’s bodies change so it’s important to know your body type and emphasize the parts you love and de-emphasize the parts you want to conceal in order to feel confident. When choosing your outfit and thinking about key essentials, keep in mind that men love women in dresses, skirts, jewelry, and heels. And don’t forget about the details! Have your nails well-manicured, wear makeup, and style your hair so it’s flowing. Your goal for the first date is to appear mysterious, feminine, and approachable. – Kimberly Seltzer

And gentleman, don’t get too casual.

The number one thing that most women find attractive is a man who looks put together and successful. I’ve peeked in many men’s closets that are still filled with acid washed jeans, pleated pants, and baseball jerseys from the days of old — not a sexy look when trying to attract that special woman today. Impress her by looking casually stylish with a few of these staples: a pair of well fitted jeans, a stylish shirt, leather jacket, and clean shoes or boots. – Kimberly Seltzer

Have some fun with your wardrobe. Invite a stylish daugher (or, if you really want to have some fun, a granddaughter) to take you shopping. Refreshing your look can be inspiring and encouraging.

Dating Etiquette in the 21st Century

When in doubt, remember that it’s hard to be too polite, and your date is probably as nervous and unsure as you are. So first, remember to keep an open mind.

Bringing the baggage of past relationships and the proverbial, “never do THAT again,” statements to your dating life will quickly turn the possibilities of the present into the pain of the past. Give someone new the chance to show who they really are, be open, and remember that they are dating, too. – Stephanie McKenzie

Dinner and/or drinks are easy go-to ideas for a first date, but try something different.

We have found that when we are able to participate in an activity this reduces the pressure of it being a “date,” and we are both able to enjoy the moment and get to know each other much easier.  – Gary Gunn

Finally, old-fashioned etiquette never goes out of style: show up on time, hold doors, etc.

How Did It Go?!

First, don’t get frustrated if a few dates don’t work out. There are lots of fish in the sea.

Remember that the purpose is simply to see if chemistry between you two exists, so it may initially feel more like a spark than fireworks. If you feel there is something there that can grow, it’s worth a second date. Ladies still appreciate a guy who picks up the tab! Men who want to go dutch on a first date is the biggest complaint of my older female clients. – Laurie Davis

And remember to just have fun.

It sounds so simple, but you need to let go of the urgency to find that perfect partner. The problem is that neediness and sense of desperation can cause your potential dates to run for the hills. Instead, make dating fun. – Kimberly Seltzer

By the time you’re half-way through the evening you’ll realize that dating in your golden years isn’t the nerve-wracking experience you may remember from your youth. You look good, so just have a good time.

Get Out There and Meet People

If you have been in a marriage or long term relationship before, it can be difficult to adjust to the dating world.

My divorced clients often have a clear understanding of what they don’t want in a future partner, and often they become fixated on this. They look for any hint of a trait their last partner had, and use it as an excuse to end a relationship prematurely. My widowed clients often feel like they have had a perfect relationship, and want similar traits in a future partner. This is completely normal, but it’s important to recognize that no two relationships will ever be the same. – Laurie Davis

Don’t get discouraged by those challenges.

You can’t dwell upon rejection. Anyone who decides not to go out with or see you again wasn’t the right fit, and gives you a clearer idea of what you want next time. – Damona Hoffman

Remember how fun it was to go on a first date when you were in your twenties? It can still be that much fun, but you need to show up with the right attitude.

Every date is an opportunity to grow and to meet someone new and interesting. Show up with the mindset that you are both there to enjoy yourself and have a good time. – Deanna Cobden

If you’ve thought about getting back in the dating scene, just go for it. If the perfect match doesn’t come along, you’ll still get to meet some new people and have some fun. If you do find a special someone, you can enjoy your golden years with someone who makes you laugh, enjoys your hobbies, and adds a little more light to your life.


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