Dating After 50: Advice for Getting Back in the Game

Dating After 50: Advice for Getting Back in the Game Image

When you picture your golden years, what do you see? Some of us imagine a crowded dining table filled with sisters, brothers, kids and grandkids all laughing and jostling for the last piece of cake. Some of us picture a hammock strung between palm trees, a cold margarita and cool breeze as we watch the sun set over the waves. One thing’s for sure — when you fantasized about life after 50, you probably never pictured getting stood up by your Tinder date at a motel bar.

Dating After 50: Advice for Getting Back in the Game Image

But hey, life happens. Some of us struggle for decades to find “the one.” Some of us have fairytale marriages until life interferes and things change. Now more than ever, men and women in their 50s, 60s and beyond are finding themselves dumped back into the senior dating pool. Wondering if you’ll sink or swim? Consider this guide your life boat.

Do You Have the Right Mindset for Senior Dating?

Before you jump into dating, ask yourself — am I ready? Like most things in life, your success with dating will be largely determined by your attitude.

“Mature women entering the dating world can be their own worst enemy,” says Dating After 40 Mentor Rosalind Sedacca. “If you approach dating with the mindset that all the good men have been taken, there's no one worthwhile out there, I'm too old to attract a quality partner, I'm too heavy to find a love relationship, dating isn't worth the effort, or with any other self-defeating belief system​, you'll prove yourself to be right.”

The same goes for the guys. If you keep telling yourself, “I’ll never find a woman as active as I am,” “I’m just not attracted to women my age,” or “These women are only interested in my money,” you’ve already decided you’ll never find love. Your mindset matters!

“Men are attracted to women who are confident, secure and believe they're a great catch,” says Sedacca. “These women live full, rich lives without being obsessed with finding a partner. However, they are available and get out to events, activities, meetings, parties, and other opportunities to meet new friends. They have a positive expectation about dating and expect to attract a great guy. Their attitude opens the door to new experiences and connections that lead to successful dating and relationships.”

Again, this advice goes for you guys, too! You attract what you put out into the world, so make sure you’re projecting confidence and positivity if you want to attract a quality partner.

What Are You Looking For?

What do you hope to get out of senior dating? The clearer the vision is of what you want, the easier it’ll be for you to plan your approach and get out there and make it happen!

So ask yourself — what do I want? You may be hoping for a soulmate to spend the rest of your life with. You may be looking for someone just to take walks with. You may even just be interested in some casual sex with hot singles. The important thing to remember is that whatever you’re looking for, it’s YOUR choice. Don’t let friends or family pressure you into feeling guilty. You deserve to be happy, whatever that means for you!

But what kind of person should you date? Marcie Rogo Co-Founder of Stitch says when looking for a partner, it’s best to let go of your filters and requirements from your 20's. “If you let yourself return to the same dating mindset you had before your first marriage, you're going to miss out on a lot of amazing people. If you're no longer having kids, think about what is important to you now and try to focus on people with similar interests. Do they want to do the things you want to do? Do you have similar lifestyles? Height, religion, and even age might not serve you well as preliminary qualifiers.”

If you’re not sure what qualities to look for, ask your friends what they love most about their partners to get some ideas.

Where Do Single Seniors Meet?

Deciding to get back out there is one thing, but where, exactly, is “out there?” In a perfect world you could just stand in your doorway and yell, “I want a date!” and the suitors would line up around the block. But in the real world, you’ll have to meet them halfway.

“Your next companion isn't going to just show up at your door, so you're going to have to do some work and be vulnerable,” says Rogo. “If you're not ready to go online, enroll in a class, start volunteering, or go on a singles trip to start meeting people in an un-intimidating environment. Go in with the expectation of making some new friends and you might find you'll come out with more.”

Meeting someone new might require you to visit new places and try new things. Not sure how to shake up your routine? Try visiting one of these places:

  • Adult art classes
  • The driving range
  • Wine tastings
  • Improv classes
  • The library
  • Dog parks
  • The beach or pool
  • Bookstores
  • Cooking classes
  • Museums
  • Community gardens
  • Volunteering events
  • Prayer groups
  • Coffee shops
  • Tennis courts
  • The gym

Although it might seem intimidating, try out some of these activities solo. If you’re paired off (even with just a pal) other singles might not be as likely to approach you.

Senior Dating Online

Probably the most difficult aspect about dating over 50 is the way you are most likely to meet someone,” says Marriage & Family Therapist Lee Berg Marchesani. “I know how terrifying and overwhelming this process seems at first, which is part of the reason I encourage my clients to have fun learning and experimenting with online dating. I think online dating services are a great place for the over 50 single to date, as you can find sites that are geared toward the over 50 crowd.”

Here are a few of the sites that are popular with the single senior crowd:

Seniors Meet
AARP Dating

“I am happy to say I am a success story of online dating,” says Marchesani. “I met my husband on Match and have been happily ‘matched’ for five years. I believe my positive experience with online dating had much to do with my attitude towards the process.”

You can create your own online dating success story by following these tips:

Set realistic expectations for dating sites. “Dating sites and apps are not meant to make choices for us,” says Linda F. Williams, MSW, Founder of Whose Apple Dynamic Coaching Services. “Even the most reputable dating sites can result in less than stellar matches. Remember, there is no computer algorithm that can weed out hidden agendas or ulterior motivations.“

Create a rational timeline. “Whether you’re in your 20s or over 50, it can take anywhere from two weeks to six months to land a solid date,” says Justin Lavelle, Communications Director for, the background checking source that helps users determine whether their online date is who they say they are. “In some cases it happens faster for younger singles only because they are less apprehensive to make the move. If you haven’t found other quality singles to date after six months, you may want to consider making some revisions to your profile.”

Share current photos. It might be tempting to post a profile pic of yourself in your 20s, but most online daters will know you’re fibbing. You still look great, so just be honest! If you don’t have many current photos, enlist a friend to help. Snap a shot outside (natural lighting is always the most flattering). Try an active photo that shows you doing something you love, whether it’s hiking, gardening or sitting in your remodeled convertible with the top down. And of course, don’t forget to smile!

Beware of catfish. “Seniors can be too trusting and are the most targeted for online dating scams known as ‘catfishing,’” says Lavelle. “Studies show that as you get older, your ability to decipher deceit declines. So you have to ask yourself, is this person who they say they are? Are they authentically interested in me or are they after something more?” Here are some tips which can help you protect yourself while diving into online dating:

  • Never share your banking info, social security number, or even your street address — scammers can use details like these to steal your identity, and your money!
  • Don’t send money to anyone you’ve met online and don’t help them out by paying a bill. The person you think you’re helping might be someone else entirely — someone who’s only online to scam seniors.
  • Consider keeping personal details like your home address, workplace and other specifics private until you meet in person.

Remember, online or off, if you feel in your gut that something isn’t right with your date, you’re probably right. There are plenty of fish in the sea — so throw that catfish back and keep moving!

7 Lucky Dating Tips for Seniors 

  1. Keep the communication lines open. “Communicate your expectations upfront and recognize when your date does not share those values,” says Williams. “Their conversation and actions will reveal who their true character. Listen closely and follow your intuition. It is better to cut your losses before making an emotional investment into the relationship.”
  2. Relax and have fun. “Once you find someone who is able to recognize, appreciate and reciprocate your values and expectations, just have fun! If it develops into something deeper, it will be long lasting if you build on a foundation of friendship first.”
  3. Don’t let jerks get you down. Some of the singles you meet might have a pretty big chip on their shoulders — and you’ll definitely notice by their bad attitudes and rude behavior. The people you meet may be unhappy about where they are in their romantic lives, and they may take it out on you. Dump them and keep moving — don’t let their negativity drag you down to their level.
  4. When it comes to your ex, keep it brief. Whether you just lost your husband of 40 years or you’re going through a nasty divorce, it might be hard not to bring up your ex. It’s okay to mention them, especially if your date asks why your last relationship didn’t work out. When they do, make your answer short and positive. Try saying something like, “I realized I wanted more out of life — and I’m so excited to have my freedom!” or “I was lucky enough to have a wonderful husband for many years, but life has decided to start a new chapter for me.” Answers like these won’t make it seem like you’re dodging the issue, but they won’t make you look like you have a ton of emotional baggage either. Win-win!
  5. Keep things upbeat. “Talking about work may feel safe, but it’s not a good first date conversation. If you had a bad day, stay home unless you can bring a positive, approachable attitude along,” says Dating Coach and Matchmaker Terri Sloane. “Before going out, I put on some upbeat or romantic music, dance by myself in my home and think happy thoughts. I leave my past in the past. If you don’t have time to go home prior, dress for work in something ‘dateable’ like a wrap dress, a pencil skirt, or a fabulous sweater or satin blouse that makes you feel pretty. Focus on a positive mood, be aware of your posture and stand tall. Add your favorite perfume, freshen your makeup and hair and smile. Your smile is always your most important beauty accessory and a welcoming appearance enhancer."
  6. Be prepared to talk about sex. "Sex can be scary, especially if you haven't dated in 30 years, so don't let yourself get rushed into something you are not comfortable with," says Bonnie Eaker Weil, author of "Make Up, Don't Break Up: Finding and Keeping Love for Singles and Couples." "Say, 'I like you and think you are attractive, but I need more time to get to know you,' or ‘Let's have the appetizer now, and we will have plenty of time for dinner and dessert later.’"
  7. Buy some condoms. Pregnancy may no longer be a concern, but sexually transmitted infections and diseases don’t care what your age is. Some diseases may not show any outward symptoms and some people may not even know they’re infected. Here’s a shocking stat — one in six infected U.S. citizens don’t know they have HIV. So wrap it up! And when using latex condoms, remember to use a latex-friendly lube (get a free sample of any of Astroglide’s latex-friendly lubes here). 

"There is never a time or place for true love. It happens accidentally, in a heartbeat, in a single flashing, throbbing moment." ― Sarah Dessen, The Truth About Forever

It can feel exhausting to continue searching for romance, but remember that the next door you open might just lead to love. And if you find a shortcut, don’t be too shy to share it! We’d love to hear dating tips from seniors who’ve found love later in life. Feel free to tweet your tips and questions to @Astroglide!


Images are for illustrative purposes only.

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