17 Reasons Dating in Your 50s Is So Challenging, According to Experts

Therapists and relationship coaches explain why dating at middle age comes with its own set of challenges.

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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 that 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 are many particular challenges that come with dating as a 50-something. Here, therapists, relationship coaches, couples counselors, and more explain why dating is so much harder at mid-life.

1
You may lack confidence.

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Unlike dating in your 20s, you might simply fear that you're just too old to be in the game in your 50s—and that shakes your confidence to the core. "You may feel limited, afraid, and self-conscious because you are aging, but don't let that stop you from living your life," says health and wellness coach Lynell Ross. "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. If you can be open to new possibilities, dating can actually be easier as you get older."

2
You feel out of practice.

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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 gave it a chance.

"Loss of familiarity or being 'out of practice' can lead to poor choices or habits, and consequently, disappointment," says Carissa Coulston, PhD, a clinical psychologist and relationship writer for The Eternity Rose. "It can be tempting to give up on over-50s dating if you have a disastrous first date. 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."

3
Or disconnected from the dating scene.

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You might have less energy not just for dating in your 50s, but for everything—and that can create additional challenges when it comes to your romantic life. "Getting tired around 10 p.m., or even earlier, makes it harder to meet new people. If you do decide to go to a bar, it is likely that you don't really know and enjoy the music they play, which makes you uncomfortable already before you meet new people," says Robert Thomas, licensed sex therapist and co-founder of men's health site Sextopedia.

4
You put a ton of pressure on yourself.

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In your 50s, you might face a lot of negative self-judgements that make it hard to attract the love you deserve. "You could be putting additional burdens on yourself by focusing on all your undesirable personality traits or threading over the emptiness that has grown in you after each and every unsuccessful date," Thomas says. "If you are one of those people, it's time to accept the truth and let go of the troubling emotions."

5
Divorce is a major factor.

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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. And then there's the challenge of finding someone who will accept and even participate with your children."

6
You have baggage—and so does everyone else.

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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," Coulston says. "Stick to neutral ground and discuss other topics such as hobbies instead."

7
You're emotionally drained.

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Dating in your 20s was about just plain fun. But dating in your 50s can mean juggling romance with the responsibilities of caring for children, or 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."

8
Compromise is harder than it used to be.

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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. "It can make you less willing or interested in compromising for someone else. 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."

9
You have less patience.

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You might have felt less resistance in your younger years to adopting someone else's way of doing things—because your own 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."

10
You have fewer single friends.

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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 both your exposure to the dating pool, and also to an endless supply of wingmen or wingwomen 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."

11
The rules of the game have changed.

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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."

12
You dread technology.

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To that end, the technology piece of dating can deter people over 50 from getting back in the game. "A lot of middle-aged people are afraid of online dating," Darné says. But, he warns, "the person who is unwilling to learn or make adjustments is likely to face more challenges in the dating scene."

13
You feel like you could be a target.

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Whether you feel like you might be the target of an elaborate scam a la a Dateline investigation, or you feel just plain cautious of more run-of-the-mill misrepresentation when online dating, you might fear becoming a target by putting yourself out there. "In your 50s, you long to have someone for both companionship and intimacy, and because of this, you also become an easy target for scammers and people who will only take advantage of you," says Celia Schweyer, a dating expert at DatingRelationshipsAdvice.com. "But there are also genuine people out there who are looking for the same thing as you are; you just have to sift through the bad ones to find your perfect match."

14
You can't help but compare.

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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," 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. 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. Even if they get close, the pressure of the comparison can kill a lot of fledgling relationships."

15
Your sexual health is different.

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Every individual is unique, of course. But as a group, singles over 50 are likely contending with a different sort of sexual health profile than they once were. "Men may suffer with inconsistent erections, which are interrupted more easily, and by a greater number of factors. Post-menopausal women may view their bodies and sexual desire very differently than when [they were] years younger," says relationship counselor and sex therapist Andrew Aaron, LICSW.

16
The dating pool is smaller.

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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."

17
You might just be avoiding being alone.

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You might be thrilled to be single and mingling in your 50s. Or maybe you're upset to find yourself in this position. And 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.

Alesandra Dubin
Alesandra Dubin is a lifestyle editor and writer based in Los Angeles. Read more
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