The Best Way to Meet Men in Real Life (Even If You’re Nervous)

If you’re an older woman trying to find a romantic relationship in the real world, you’re not alone. I’ve worked with thousands of single women over 50, and I hear this all the time: 

“I’m tired of online dating apps. I want to meet a great guy in real life.” The kids call it "IRL."

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But no one teaches us how to approach new people in real life. We've been quite literally discouraged. We were raised being told, "Don't talk to strangers." So it makes perfect sense that meeting potential partners "in the wild" feels scary, especially if it’s been a while since your last actual date.

That’s why I use a mindset tool to help mature adults navigate the experience of meeting people while out and about. It's called the “When in Roam” scale. It’s based on a simple idea: no matter your age or relationship history, you can build confidence, connect with new people, and open the door to real love again.

Check out the "scale" and decide what stage you are in. I learned about each stage and the coaching for each stage from the Handel Method.

Stage One: The Head-Down Phase

You’re out in public places, but you’re not looking up. You’re not making eye contact. You’ve decided the dating scene is a bad idea—or just not for you. If this is you, your first step is simple. Every time you go out, make "happy eyes" with two people. As Tyra Banks says, smize= "smile with your eyes."

Whether you’re in a coffee shop, walking group, or waiting in line at the grocery store, practice looking up and showing warmth with your eyes. It doesn't need to be someone you're interested in or even someone your age or "type," anyone will do. Just get those eyes up and on other people!

Stage Two: You Wish You Could Meet People

You want to meet a potential partner, but you’re not sure how. Your assignment: small talk. It’s the best way to start. Just have a Q and A with someone.

Ask the nice guy at a tour of your local art museum what he thought of the exhibits. Comment on someone’s dog at the park. Chat up a stranger about what they are buying at your favorite local store. Compliment someone. Ask for directions. Heck, ask what time it is if you are too shy to come up with something spicier. 

You’re not trying to score a date on the spot—you’re just building the muscle of reaching across the great divide and striking up a dialogue.

Challenge yourself to interact with a stranger each time you leave your home. Your goal is at least one back and forth. If it goes further, advance to stage 3!

Stage Three: Start the Real Conversations

Stage 3 is for people who can strike up conversations but are still a little shaky on how to sustain a conversation.

If you're at this stage, you know how to make an overture to safe people, but it’s time to test your limits--try new people and try extending the conversation. This could be with someone you are standing next to on a street corner. Or at a speed dating event, a meetup group, or after church or pickleball court. 

Maybe you spot someone in your age group and ask what brought them to the event or location. The goal? Build comfort talking to seemingly single men—without pressure. Read my blog on how to flirt naturally. Now you are officially practicing flirting, but start with people who seem safe and kind (and single). Feel free to ask friends to set you up for this by inviting you to places where they may be!

Stage Four: Get Comfortable with Rejection

In Stage 4, you aren't afraid of chatting someone up, but some people might still intimidate you. This is where the real dating practice begins. You are to start initiating conversations with men to whom you could actually be attracted, with no care about their response.

That cutie in your book club? The attractive man at your gym? Someone sitting alone at the bar? Say hello. Ask a question. Now you are actually "going for" being blown off or rejected, to toughen your skin on purpose. Flirt out of your league, by design. 

Rejection is a natural part of dating in the real world and the online dating world alike. I want you to build up a callus for a good reason! If you can handle this without taking it personally, you're so much better off down the road.

Stage Five: You Can Talk to Anyone—Now Be Picky

If you are at stage 5, meeting people IRL isn't your problem. Your problem is you're too distracted by all the people around you. You're the social glue because you are so good at it, and may be a social crutch or wingperson for others. Time to focus on what you really want and need, and laser in on the people you most want to meet, and let the rest go.

You’ve built confidence. Now your job is to stop wasting time with the wrong matches. Just because you’re charming doesn’t mean every single man is a good match. Be selective. If someone shows red flags, walk away quickly. If you’re not feeling a real connection, don’t exchange contact information just to be polite.

Hopefully, you've figured out what stage you are at and the appropriate coaching to move forward in your mission to meet your next love in real life. But where?

Where Do You Meet Single Men in Real Life?

I always giggle when people ask me WHERE to meet single people, as if it's a really useful question. If you're asking that question, something else is likely stopping you, besides this supposedly geographical quandary.

The answer to where to meet single men in real life is: literally EVERYWHERE!

Single men are not just on online dating platforms. They’re at your local community center, the park, the grocery store, your Saturday morning coffee shop, your family and friends' life cycle events and parties, and even your grandkids' school performances. And of course at gyms, churches, temples, bars, and restaurants. They eat 3 times a day, just like you!

You’ll meet the best people when you follow your own interests. Join a hiking, running, golf, tennis, chess club, attend a class, or start a book club and ask each friend to bring a single man who would dig the books you're proposing.  These are all great ways to meet like-minded people—and they come with the bonus of expanding your world even if they don't become your boyfriend (maybe they know your future boyfriend ;)

Real Life vs Online Dating Sites: Why You Should Do Both

Real life gives you a better chance to evaluate someone’s energy, sense of humor, and presence. You can tell a lot about someone just from body language and tone. But online dating sites and online dating apps do have advantages. On most popular dating apps, like Coffee Meets Bagel or other paid subscription platforms, like Tinder, you know the person is looking for something—whether that’s casual sex (Tinder), a long-term relationship (Coffee Meets Bagel), or something in between (Match).

I believe that being on dating sites has the energetic advantage of sending the message to your subconscious that you are seriously looking, and that helps your chances of meeting someone in real life, too! And let's remember, once you meet someone online, you're going to have to meet them in real life soon, so best to get good at both.

Never put all your eggs in one basket, whether it's an online platform or real life. The best way to meet the love of your life is to believe that you will, and the more actions you take in that direction, the better!  

Conversation Beats: How to Talk to a Potential Match IRL

There are five key parts to every "first" interaction.

1. The nod: Make eye contact. Smile. This is the silent invitation to connect.

2. The one-liner: Have a few openers ready. “Are you from around here?” “What brought you to this event?” “Mind if I join you?” These can work in a public place, in a social group, or even at high school reunions.

3. The follow-up question: Ask about something he is wearing or that relates to the place you both are. Avoid yes/no questions so a conversation gets going.

4. The check-in: Once you know you're officially flirting, you can ask: “How’s this going?” This makes it clear you are flirting and want to know if he likes it. It's a playful way of checking in to see if you are reading the vibes correctly and should proceed with more banter.

5. The exit: If it’s going well, ask if he’d like to meet for coffee sometime. If it’s not going well, thank him for the conversation and move on with a wink and a smile. Next!

Next Steps

The best way to meet men is to show up. Leave your home. Say yes to invites. Start conversations. Whether you’re a single parent, an older woman who’s been out of the game for a long time, or someone navigating life after difficult past relationships—it gets better!

For more inspiration, watch the YouTube interview I did about meeting people in real life. 

Dating after 50 to find a long-term partner means dating websites and IRL.

I know many women who've successfully met wonderful men IRL. You could be the next one. You deserve a committed relationship. You deserve good company. And you’re not too old, too late, or too far gone to find it. 

I'll be with you every step of the way!

Frequently Asked Questions

Where is the best place to meet single men in real life?

Look for events in your local area, such as meetup groups, community workshops, art classes, or book clubs. Casual members of online communities or social media groups often organize real-world get-togethers. Start showing up where like-minded people gather.

Should I still use online dating sites?

Yes. Online dating platforms can be a great option, especially if you're specific about what you're looking for. Use the free version first, then decide if a paid subscription is worth it. And always schedule a video chat before an actual date to screen potential matches.

How do I handle nerves when talking to new people?

Start with small talk. The first place to build confidence is in low-stakes environments: the grocery store, local store, or dog park. Practice being warm and open without needing a perfect outcome.

Is there a red flag if someone won’t share personal information or dodges questions?

Yes. Transparency is key for building a real connection. If they avoid basic questions or resist conversation, they might not be ready for a romantic relationship.

I haven’t dated in a long time. Am I too old for this?

Absolutely not. Many adults over 50 are reentering the dating scene. You’re part of a powerful wave of older adults looking for meaningful connections. And the right person is looking for you, too.