This is How to Date After Middle Age

I'll admit, I was always under the expectation that my husband and I would live out our golden years side by side, after we built our lovely ranch in Southern Oklahoma. Life took a bitter turn when our marriage crashed and burned. Suddenly at 55, I found myself alone, and for the first time in a long time, I experienced a deep loneliness that I hadn't before. So, I did what anyone would do at my age… I turned to dating apps. After all, isn’t that where everyone seems to go these days?

Some of my long-married friends have shared that they sometimes feel a twinge of envy. At first, I was shocked. Envious of me? For being single? By now, many in our Gen X generation have navigated the challenges of raising kids, financial struggles, multiple marriages, dry spells in intimacy, and career changes. While building a life with a longtime partner has its joys, there’s something exhilarating about starting over with someone new—someone unconnected to your past. You can be anyone! So, even though it was difficult, being single had its perks.

For me, reentering the dating world after two decades has been eye-opening. The landscape is brimming with fascinating trends and discussions, such as open marriages. Today, when my happily partnered friends and family ask me if dating after 50 is harder, I tell them it’s not harder—just different. But let’s be honest, was dating ever simple?

For those of us who are single, dating after 50 feels like a second chance—a new opportunity to explore love and connection in a meaningful way. Without further ado, here’s my advice, drawn from both my own experiences and the stories shared by those around me. And if you’re looking for even more tips, be sure to check out Senior Dating 101: A Complete Guide.

How to Meet Someone New

First things first! How do you even meet someone new? There are plenty of ways to put yourself out there and connect with curious, inspiring, and beautiful people. In fact, there’s no shortage of dating apps and social activities designed for those over 50 who are eager to meet new people. The numbers back it up—36 percent of adults aged 65 and older report being single, and 29 percent of those aged 50 to 64. We’re all looking for something, whether it’s a short-term or a long-term relationship. So how do you get started?

Here’s a quick breakdown:

Hit the Dating Apps

The first, very obvious answer is dating apps. That is also where I met my own partner, who is a total gem of a human being. He’s smart, talented, successful, and gorgeous inside and out. Our first conversations were so easy, and it felt like I’d known him forever. My favorite go-to apps were eHarmony, SilverSingles, and OurTime. You can check them out for yourself.

Join a Class or Workshop

From yoga classes and wine-and-paint nights to salsa dancing, woodworking workshops, cooking classes, and even gardening groups, there’s no shortage of ways to meet people and create meaningful connections. Each activity offers a unique opportunity to bond over shared interests, whether it’s learning to prepare a gourmet meal, building a handcrafted birdhouse, or planting seasonal blooms. Participating in these activities not only helps you pick up new skills but also places you in environments where conversations flow naturally, making it easier to break the ice and connect with like-minded individuals.

Volunteer for Good Causes

Volunteering doesn’t just make you feel good—it’s also an amazing way to meet kind and wonderful people. Go beyond the usual charity options and look for niche opportunities. For example, help organize a local film festival, join a community garden project, or assist at an animal sanctuary. Working side by side with others is an easy way to form connections naturally.

Attend Pop-Up Events and Local Gatherings

Pop-up dining events, immersive theater performances, and themed parties can be goldmines for meeting new faces. Keep an eye out for unique events on local Facebook groups. Show up with a smile and an open mind—you never know who might strike up a conversation at the cheese fondue station.

Say Yes to Invitations

When someone invites you to an event, a party, or even a random Tuesday coffee outing, say yes! Expanding your social circle often starts with showing up, even if it’s outside your comfort zone. The best connections sometimes happen when you least expect them.

Red Flags to Watch Out for When Dating in Your 50s

Dating in your 50s can be thrilling and full of opportunities, but it’s also a time to be vigilant about spotting red flags. Because let’s face it, a lot of people are great, and a lot of people aren’t. These warning signs can save you from unnecessary heartache and help you invest your time in relationships that truly align with your values and goals.

Here are a few common red flags to keep on your radar:

1. The Eternal Child

If your date seems more interested in being cared for than being a true partner, it’s a major red flag. This type of person might rely on you for emotional or financial support, expecting you to solve their problems or take on a nurturing role in their life. For example, they may frequently complain about their job or financial situation while making no effort to improve it, leaving you to pick up the pieces. A relationship works best when both partners bring their own strength and stability to the table, not when one person takes on a caregiver role.

2. Jealousy Toward Your Family

Someone who competes with your family members, especially your children, should raise immediate concerns. For instance, if they make passive-aggressive comments about the attention you give your kids or criticize your choices in how you prioritize family time, it’s a sign they might struggle to respect your existing relationships. A healthy partner should understand and support the important role your family plays in your life, not view them as rivals for your affection.

3. The Opportunist

Be wary of anyone who seems overly interested in your financial situation or steers conversations toward money, investments, or extravagant plans early on. Opportunists often look for ways to benefit financially from a relationship, whether it’s through subtle manipulation or outright schemes. For instance, someone might suddenly bring up a “great business opportunity” or suggest joint investments before you’ve even established trust. If their focus seems to lean more on your wallet than your personality, it might be time to take a step back.

4. Excessive Negativity

A partner who constantly complains about their life, previous relationships, or even trivial matters may not be emotionally ready for a healthy relationship. While everyone has their moments, excessive negativity can drain the energy from a relationship and leave little room for joy or growth. If you notice a pattern of constant criticism or a “woe is me” attitude, it’s worth considering whether this person is capable of building a positive and supportive connection.

5. Controlling Behavior

If your date tries to dictate your choices, from what you wear to how you spend your time, this is a serious red flag. Controlling behavior can start subtly, such as questioning your decisions or making backhanded comments, but it can escalate quickly. A healthy relationship thrives on mutual respect and independence, not power dynamics or manipulation.

Best Practices for Dating in Your 50s

You might feel like you’re stepping into a whole new world, but with the right strategies, it can be an exciting and rewarding experience. Here are some best practices to help you date with confidence and clarity.

Know What You Want

Before diving into dating, take some time to reflect on what you’re truly looking for in a partner. Are you seeking companionship, a casual relationship, or a long-term commitment? Creating a list of five “must-have” qualities and five deal-breakers can help clarify your priorities. For example, if shared family values or a love of travel are important to you, use these as your guide when meeting new people. By staying intentional, you can focus your energy on partners who align with your goals.

Takeaway: Define your priorities by listing five essential qualities and five deal-breakers to screen potential partners.

Prepare Some Fun Banter

First dates can feel nerve-wracking, but a little preparation goes a long way. Think of your conversation as a “highlight reel” of your life—stories about your interests, experiences, or passions that showcase who you are. For example, if you’re a dog lover, share a funny or heartwarming story about your pup. If you love gardening, talk about your favorite plants to grow. Keep the tone light and engaging, and leave room for your date to respond and share as well. Avoid overly rehearsed scripts but aim to feel comfortable discussing yourself in a way that invites connection.

Takeaway: Jot down a few conversation starters and personal stories that highlight your interests and hobbies, helping you feel more at ease.

Embrace Technology

I’ve said this once, but I’ll say it again… dating apps are a fantastic way to meet people, especially if you’re busy with work or family. Apps like eHarmony, SilverSingles, and OurTime cater to individuals over 50 and can help you connect with a wide range of people. The convenience of online dating allows you to browse profiles at your own pace and interact with potential matches from the comfort of your home. Plus, it’s a great way to practice setting boundaries and understanding what you want in a partner.

For example, some people use apps to narrow down behavioral preferences, like identifying partners who are communicative and proactive about planning dates, as opposed to those who only want to text endlessly. It’s a learning experience that helps refine your expectations.

Takeaway: Give dating apps a try—they’re convenient, popular, and a great way to explore what you’re looking for in a partner.

Expand Beyond the Apps

While dating apps are helpful, don’t limit yourself to virtual connections. Opportunities to meet someone special exist in everyday life. Keep your eyes open while attending events, joining community groups, or exploring hobbies. Whether it’s a new friend from a cooking class, a fellow parent from your child’s school, or someone you meet at a neighborhood event, these interactions can lead to unexpected connections. Speed dating events are also making a comeback and can be a fun, low-pressure way to meet multiple people in one evening.

Takeaway: Be open to love in real life, from community events to speed dating. Sometimes, the best connections happen offline.

Have a Feel-Good Date Look Ready

Looking and feeling your best on a date starts with a great outfit that’s both comfortable and flattering. Aim for something that highlights your personality while adding a touch of subtle elegance. A classic pair of jeans with a stylish blouse or a sleek dress paired with your favorite accessories can strike the perfect balance between casual and polished.

For video dates, focus on the details that stand out on camera. Choose a top in a color that complements your skin tone, and add a touch of makeup like a flattering lipstick or a bit of mascara to enhance your features. Keep the background simple and your look well-coordinated to let your personality shine through.

It can really help you feel prepared if you already have an outfit ready in advance. It means less stress when date night arrives.

Takeaway: Keep an outfit on hand that makes you feel confident and attractive, so you’re always ready to step into a date feeling your best.

Build Your Resilience—it’s Okay if it Doesn’t Work Out

Dating can bring disappointments, but rejection isn’t failure—it’s part of the process. Not everyone will be a match, and that’s okay. Each date is a chance to learn more about your preferences and what you truly want.

Remember, you’re not alone; many in the 50+ dating pool are navigating similar experiences. Approach each interaction with compassion, and if a date doesn’t feel right, move on without judgment.

Takeaway: Celebrate your effort and growth. Every date is progress, even if it doesn’t lead to a match.