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16 Challenges of Dating in Your 50s—and How to Overcome Them

Relationship experts share their best advice for having a smooth dating experience in your 50s.

Remember when dating was about meeting a potential mate through a friend and getting to know them over dinner and a movie? Well, if you're dating in your 50s, you know that it can be so much more complicated than this idyllic scene of your younger years. You might be reemerging on the dating scene following a long hiatus, perhaps after being divorced or widowed—only to find that the rules (and technology) of the game have changed. In fact, there can be many particular difficulties that come with finding a partner in mid-life. Keep reading to hear from therapists, relationship coaches, and couples counselors about the biggest challenges of dating in your 50s—and how to overcome them.

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You lack confidence.

older man sitting on a chair and looking sad and confused
pixelheadphoto digitalskillet / Shutterstock

"When people over 50 have been in long-term relationships for many years and go through a divorce, breakup, or experience the loss of a loved one, they can feel less confident than in their younger years because of having been disconnected from the dating scene for so long," explains Lisa Lawless, PhD, sexual health expert and CEO of Holistic Wisdom.

But it's important to focus on the positive aspects of dating at this age rather than what your nerves may be telling you.

"By the time people get to their 50s, they are usually not just older and wiser, but they are kinder, more forgiving, and more understanding," says health and wellness coach Lynell Ross. "If you can be open to new possibilities, dating can actually be easier as you get older."

You feel out of practice.

A senior latinx couple enjoying a picnic on a blanket in the woods and playing cards

In your 50s, you might feel like you've been out of the game for too long to even know how to play. And that insecurity can make you feel like giving up on a new relationship before you even really give it a chance.

"Loss of familiarity or being 'out of practice' can lead to poor choices or habits, and consequently, disappointment," say experts at The Eternity Rose.

"It can be tempting to give up on over-50s dating if you have a disastrous first date," they note. "However, 'disastrous' first dates do not always mean that there is no potential in a relationship forming. First dates can go poorly for a number of reasons; anxiety is a very common one."

You put a ton of pressure on yourself.

Man waiting for date to arrive for romantic dinner

"It may feel like a lot of pressure to date because people are often expected to be with a partner when they are older," notes Lawless. But it's best to be patient with yourself.

"Stay encouraged, and know that many people like yourself are looking for meaningful connections that offer honesty and intimacy," Lawless says.

You have fewer single friends.

Friends celebrating a birthday

These days, you might have a few high-quality friends, rather than a whole party bus full of people to expose you to other singles. That reduces your exposure to the dating pool, as well as to an endless supply of wingmen or wing women to pump you up.

"Much of the fun that came with being single when you were younger was due in large part to having lots of single friends to hang out with. However, when you're in your 50s, the vast majority of your friends are likely married or in serious relationships," says dating expert and writer Kevin Darné. "A lot of people are not all that comfortable going out to places alone, and their number of outings is based on the availability of their friends."

Lawless suggests clearing this hurdle by seeking out social groups "that cater to people in your situation for help and advice." She also recommends working with a mental health therapist to build up the confidence needed to put yourself out there.

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The dating pool is smaller.

older gay white man having coffee across from other man
Monkey Business Images / Shutterstock

The reality is, the dating pool is smaller at 50-plus than it was in earlier decades. And that can prove downright daunting.

"Many of us worry all the good ones are gone at this age and we had better hurry up and get a partner established so we don't miss out on potential," says Dana McNeil, LMFT, founder of The Relationship Place. "Acting from a scarcity mindset means we may overlook some red flags."

The rules of the game have changed.

Couple clinking glasses of wine

Remember the etiquette that defined courtship and dating when you started out on the scene? Yeah, those days are long over.

"Most of us who have resurfaced in the dating world find it very different than it was when we were younger and single," says Holly Woods, PhD, of Holly Woods Coaching & Consulting. "The rules of dating and relationships have changed and we have to learn new rules. Yes, that means conventions of chivalry, courtship—and certainly factors like technology, too."

But Laura Wasser, a divorce lawyer, family law and relationship expert, and chief of divorce evolution at, says you shouldn't let your age "hold you back from exploring new experiences or getting out of your comfort zone." Remain open-minded about "trying new things and meeting people from different backgrounds," she says.

You dread technology.

Older man using cellphone

To that end, the technology piece of dating can deter people over 50 from getting back in the game.

"It can feel very intimidating to share personal details with strangers online, and fears about becoming a target of a scam or harm are not an uncommon or unrealistic concern," shares Lawless.

But, as Darné notes, "the person who is unwilling to learn or make adjustments is likely to face more challenges in the dating scene."

Luckily, several dating sites are specifically designed for older singles.

Or you're too focused on social media.

man swiping and liking on a dating app on his phone

No matter our age, we can all fall victim to FOMO (fear of missing out), which is a concept pegged to social media use and comparing our lives to those that others are projecting.

"FOMO can be a real buzzkill when you're trying to make connections," says Wasser. "Put down your phone and give your full attention to your date—it's time to create memories, not just scroll through them!"

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Divorce may be complicating things.

Senior asian couple fighting on the couch

Many singles over 50 are divorced—at least once, if not multiple times over. And that adds layers of complexity when it comes to building new relationships.

"Many 50-somethings are divorced and come with an ex and kids. These factors can both complicate future relationships," explains Gail Saltz, MD, associate professor of psychiatry at the New York Presbyterian Hospital Weill-Cornell School of Medicine.

"They can make being able to be fully engrossed with someone new more challenging," Salta says. "And then there's the challenge of finding someone who will accept and even participate with your children." The key here is patience and knowing what you want out of a relationship.

You can't help but compare.

Women having a disagreement in a coffee shop cafe

Considering how many relationships you've experienced by the time you reach your 50s, you might find yourself comparing all new partners to the old ones, and that can be a form of self-sabotage.

"It is not uncommon for daters in this age range to be coming into dating after a 20-plus year marriage," says professional dating profile writer Eric Resnick. "Sometimes people approach dating with an eye towards what they don't want as opposed to what they do want."

"Unfortunately, this negative perspective tends to just draw in the same type of people they want to avoid, while scaring off the people who would be perfect for them," Resnick explains.

"On the flip side, some who are widowed tend to use their departed loved one as the yardstick by which they measure future dates—but it is impossible for anyone to hold up against the love of your life," Resnick notes. "Even if they get close, the pressure of the comparison can kill a lot of fledgling relationships."

You have baggage—and so does everyone else.

Men talking over beers

Even if you and your dating partners aren't divorced or widowed and don't have children, everyone likely has plenty of relationship experience by the time they hit 50. And whether you call that baggage (a word loaded with negativity) or just plain experience, these past relationships impact the realities of dating later in life.

"It's very tempting to find common ground with a new date by asking about their relationship history. However, bonding over your baggage is never a good way to start a new relationship," The Eternity Rose says.

"It's important to remember that everyone has their own suitcase to unpack," advises Wasser. "Be open, honest, and understanding—this will help build a solid foundation for your relationship."

You're emotionally drained.

Older woman drained laying in bed tired

Dating in your 20s was probably about having fun. But dating in your 50s can mean juggling romance with the responsibilities of caring for children, parents, or maybe even both.

Your 50s is "the sandwich time between kids and aging parents," says Saltz. "Because of this, a new relationship has to endure the high stress of this time period, which can also include moving-up-in-work stress, aging-parents stress, financial burdens, and kid stresses. These all impact the emotional energy left over for a relationship."

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Compromise is harder than it used to be.

Mature, older senior gay male couple, affectionate and holding hands, walking down the main street of a small village in the Hamptons.

When you're younger, compromise is an ingrained part of daily life as you grow and evolve. But by your 50s, "you have some set patterns of behaving and feeling, some set values, goals, ideas about how your life should go, and it can make you less flexible to accommodating someone else," Saltz says.

"You will not be growing up together, you will be grown up and trying to fit with someone—finding someone who fits is more challenging," Saltz adds.

You have less patience.

Couple having a disagreement

You might have felt less resistance in your younger years to adopting someone else's ways of doing things—because your own ways weren't so firmly set in stone.

"A major reason as to why dating is so much harder in your 50s is because you're much more set in your ways and values," says certified mental health consultant and relationship expert Claire Barber. "This isn't a bad thing; it just means that it can be harder to get into the flow of dating because you have less patience for people who you don't vibe well with."

Your sexual health is different.


Every individual is unique, of course, but as you age, your sexual health changes.

"People over the age of 50 often begin to see sexual health issues emerge, such as different levels of erectile dysfunction (ED), female sexual dysfunction, vaginal dryness, and more," says Lawless. "When one is challenged sexually, it can feel intimidating to date others and may cause challenges to self-esteem and a reluctance to be vulnerable in new partnerships."

You might just be avoiding being alone.

Lonely man upset by himself

You might be thrilled to be single and mingling in your 50s. Or maybe you're upset to find yourself in this position. If you're in the latter category, the fear of being alone might compromise your decision-making.

"We sometimes make the mistake of rushing into the next relationship so we don't feel alone," says McNeil. And another warm body does not automatically make a meaningful, enduring match, she points out.

Dana Schulz
Dana Schulz is the Deputy Lifestyle Editor at Best Life. She was previously the managing editor of 6sqft, where she oversaw all content related to real estate, apartment living, and the best local things to do. Read more
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