Dating After 50: How to Flirt and Create Attraction (Without Feeling Awkward)

If you’re dating after 50, it can be challenging to know how to flirt and create attraction. Watch this video to learn how!

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If the thought of flirting makes you cringe a little… you’re not alone. Many of my clients over 50 tell me, “Flirting feels fake.” Or, “I don’t know how to flirt anymore!”

Here’s the good news: flirting isn’t about acting like someone you’re not. It’s about showing genuine interest, confidence, and a little playful energy that says, “I see you—and I like what I see.”

Attraction isn’t just about physical looks or sexy banter—it’s about how you make someone feel in your presence. Ready to flirt like the fabulous, radiant woman you are? Here are 5 simple ways to create connection and chemistry after 50 (without trying too hard).

How to Flirt and Create Attraction

1. Make Eye Contact and Hold It

This is one of the most powerful, low-effort ways to flirt—especially in person.

When you meet someone or walk into a room, don’t scan the crowd or look down at your phone. Look people in the eye. Hold the gaze for just a beat longer than usual—and smile. That moment of eye contact can say “I’m confident, I’m open, and I’m interested.”

Try this on your next date or even with your barista. Practice makes it feel natural!

2. Give a Genuine Compliment

Flirting after 50 doesn’t mean playing games. A sincere, well-placed compliment can spark instant attraction. Instead of complimenting looks (which everyone does), focus on something unique—his voice, his sense of humor, his insight, or even his shoes.

Try this:

“I love the way you think. That’s such an interesting perspective.”

Or…

“You have a great laugh. It’s contagious!”

Men light up when they feel seen beyond the surface (so do women!).

3. Exhibit Playful Curiosity

If the idea of flirting makes you uncomfortable, let’s reframe it. Flirting is curiosity + warmth + a dash of sparkle. Ask open-ended questions with a little twinkle in your tone. Laugh if you think he’s funny. Share something personal and light. You’re not interrogating—you’re inviting.

Instead of:

“So, what do you do?”

Try:

“What’s something you’re passionate about that lights you up these days?”

Playful questions + genuine listening = connection.

4. Lean In—Literally and Emotionally

Flirting is as much about body language as it is about words. Lean in slightly when he’s speaking. Nod. Use your hands when you talk. Mirror his energy in a natural way. All of these subtle signals say: “I’m engaged and enjoying this.”

Emotionally, let yourself be a little unguarded. Be willing to be a bit vulnerable or playful. Attraction deepens when we feel someone’s authenticity.

5. Step Into Your Confidence

Confidence is the most attractive quality at any age. Walk into dates knowing you are a woman of value. You’ve lived, you’ve loved, and you’re still curious and open to what’s next. Your confident energy is irresistible.

And if flirting still feels awkward? That’s okay. You don’t have to get it perfect. The most attractive thing is when you show up fully as you—with humor, warmth, and heart.

How to Flirt – Final Thoughts

Flirting is really just an energy—a lightness, a spark, a willingness to be present and playful. It’s not about seduction; it’s about connection.

So the next time you’re on a date, try this: take a breath, make eye contact, smile, and lean into the moment. Your aliveness is your allure.

And remember… it’s never too late to go on your last first date.

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If you’re feeling stuck in dating and relationships and would like to finally find your person, sign up for a complimentary 45-minute love breakthrough session with Sandy https://lastfirstdate.com/application

Join Your Last First Date on Facebook https://facebook.com/groups/yourlastfirstdate

Get Sandy’s books, Becoming a Woman of Value; How to Thrive in Life and Love and Choice Points in Dating; Empowering Women to Make Healthier Decisions in Love and Love at Last: True Stories of Falling in Love Later in Life

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