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Dating Challenges Blog Articles

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Attachment Styles

June 25, 2026

How to Stop Repeating Old Relationship Patterns

A woman leaves an unhappy marriage, promises things will be different, then the same fights and slow disappointment return. That is not bad luck.

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Online Dating

June 18, 2026

The Complete Guide to Apps, Profiles, and Showing Up Like Yourself

Let me be honest: many women treat online dating like a chore, then feel demoralized. I want to help you show up as yourself.

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Getting Started

June 11, 2026

The Complete Guide to Finding Love Again After 50

You're over 50 and dating feels exhausting. I've helped hundreds of women at the edge of the dating pool. Here's your complete guide.

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Trust

May 28, 2026

7 Things People Lie About in Dating Over 50 (And Why It Matters More Than You Think)

People lie in small, strategic, sometimes unconscious ways. I've seen it derail good matches on profiles, first dates, and beyond. The 7 lies.

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Compatibility

May 7, 2026

8 Things High-Caliber Mature Men Actually Want

I coach men too, and the cliches are wrong. High-caliber mature men want something more interesting. Here are 8 things they actually want.

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Sex

April 23, 2026

Should I Have Sex on the 3rd date?

I'm not judging you if you followed the third-date rule. Here's why it can backfire, and what to weigh before sleeping with someone new.

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Dating Challenges

April 16, 2026

Where Are the Good Men?

I hear it every week: "Where are the good men?" If you think they're all taken or missing, let's talk about what's really happening.

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Sex

April 9, 2026

Sex Over 50: What Nobody Tells You About Desire

I'm saying what most women over 50 think but don't say: can sex still be great? I brought in an expert who changed how I see desire.

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Healing

March 12, 2026

Handling Rejection After 50 Without Losing Hope

Rejection hurts at any age. The work isn't avoiding it; it's moving through it without making it a verdict on your worth.

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Dating Challenges

March 5, 2026

5 Dating Mistakes Women Over 50 Still Make — And How to Stop Them Fast

If you are dating over 50, here is the good news. Dating can actually get better with age. Not easier. But better.

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First Dates

February 12, 2026

4 Types of Questions to ask on the First Date

Dating after 50? Chemistry isn't the only thing that matters. These 4 first-date questions help you spot a partner who fits your real life.

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Confidence

January 2, 2026

Self-Love After 50: 6 Hidden Obstacles That Block Love

Thinking about dating again? I say there's no expiration date on love. Here are 6 hidden obstacles blocking you. You are not too late.

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Dating Mindset

December 11, 2025

Dating Over 50: 8 Unrealistic Expectations That Keep You Single — And How to Shift Them

If you’re dating over 50 and wondering why it feels harder than ever to find your person, you’re not imagining it. The dating landscape has changed — and so have we. You’ve lived, loved, raised kids, maybe divorced, maybe lost a partner. You’ve learned a lot about yourself. But…

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Divorce

October 30, 2025

Post-Divorce Casual Dating: To Fling or Not to Fling?

I wish my kids had taken a gap year before college. Now I think divorced daters need one too, a fling year before anything gets serious.

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Dating Challenges

September 25, 2025

Thinking About Dating Older Men: But Don’t Want to Be A Nurse Or A Purse?

Dating men with more years behind them? Stop worrying you'll become a nurse or purse. I'll show you a better alternative.

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Dating Challenges

September 18, 2025

What to Expect When Dating a Man Over 50

If you’re a woman in later years looking for a mature man around your own age, there are some things you should expect. This list isn't meant to scare you—it’s to help you experience the dating scene with greater ease. First off, they might help you feel less crazy, because if…

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Dating Challenges

September 11, 2025

5 Most Awkward Dating Situations and How to Deal

Cringe stories shouldn't keep you from dating. With a little prep, you can handle 5 awkward situations and feel more confident.

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Communication

August 7, 2025

3 Do’s and Don’ts of Online Dating Banter

Good banter keeps the spark alive online. Use my do's and don'ts to move from messages to a video chat and then a real date.

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Compatibility

August 7, 2025

The Problem with "Love Languages" in Early Dating

Trying to show love but your partner feels the opposite? In early dating, love languages can mismatch like rupees and rubles.

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Confidence

July 31, 2025

Are You Undateable? 6 Things You May Not Realize

Ever Googled "Am I undateable?" If you're asking, you probably aren't. Reflective women are dateable, but there are 6 things to check.

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Communication

July 31, 2025

How Do I Get a Man to Talk to me? 5 Great Ways to Make a Conversation Flow

Feel like you're pulling teeth to get a man talking? The secret isn't more questions. It's real listening, and it makes you more attractive.

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Communication

July 24, 2025

30 Dating Questions to Ask To Get to Know Someone Better

As a relationship expert, my mission is to help you stop wasting time on dead-end dates and find someone who’s a good match for you for long-term love. By "good match," I mean you are "in sync" on all 3H's: your head, your heart, and your hoo-ha.

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Intimacy

July 17, 2025

How Women Over 50 Can Support a Partner with Erectile Dysfunction

Sex can be a big dating concern. I give you the lowdown on erectile dysfunction so you can support a partner and protect intimacy.

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Dating Apps

July 10, 2025

Top Advice for Dating App Fatigue When Every Swipe is a Soul-Suck

Dating app burnout isn't inevitable. I'll show you how to stay in the game and keep your sanity when every swipe feels like a soul-suck.

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Dating Profiles

July 3, 2025

The Worst Dating Profile Mistakes Women Over 50 Still Make—And How to Fix Them

As a dating coach, I see women over 50 sabotaging their profiles with group photos, cliches, and negativity. Here is how to fix it.

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Dating Mindset

June 19, 2025

What Do Older Women Think Men Want—and Are They Right?

What do men actually want? We explore whether mature women really know, or if we're repeating assumptions and insecurities.

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Emotional Availability

June 19, 2025

Why Do Men Ghost: Some Important Coaching

Ghosted and reeling? Here is the coaching: stop falling for people whose words don't match their actions, and choose better.

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Dating Challenges

June 5, 2025

Should I Hire a Professional Matchmaker?

Curious what a professional matchmaker really does? I sat down with Jill Dunn to talk dating app burnout and long-term success.

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First Dates

May 22, 2025

10 Key Questions to Ask on the First 3 Dates for Mature Daters

The right questions early on matter more than chemistry. I'll share my Spark Questions to help you date with clarity and have more fun.

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Online Dating

May 22, 2025

Love at First Site: How to Choose the Best Dating Site Without Losing Your Mind

As a dating coach, I help women cut through the chaos of choosing a dating site or app when there are simply too many choices.

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Attraction

May 8, 2025

How to Flirt Naturally (and Still Be Your Authentic Self): Clean and Dirtier Come-ons Included

Flirt game rusty? You do not need cheesy lines. I have natural body language tips plus clean and dirtier lines that still sound like you.

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Dating Challenges

May 8, 2025

How Women Can Avoid the Top Five Dating Mistakes

After 20 years studying dating, I found the biggest mistakes women make can be avoided. Meet your 3H voters: Head, Heart, and Hoo-Ha.

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First Dates

May 1, 2025

Most Common Third Date Mistakes to Avoid

The 3rd date is a significant milestone, it assumes you are really interested in each other and attracted– but you need to know some very important things in order to take it further.

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First Dates

April 17, 2025

Biggest and Most Common First Date Mistakes To Avoid

First dates can be nerve-wracking, but most mistakes are avoidable. Here are the biggest first-date mistakes and how to steer clear.

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First Dates

April 10, 2025

Why Do Men Talk So Much On First Dates?

Some men are narcissists. Some men are full of themselves. Most men are neither.

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First Dates

April 3, 2025

Worst Date Ideas

Bad dates are the worst. Here are my tips from 20 years of coaching for your first three dates, so you can skip the crappy ones.

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First Dates

March 20, 2025

What is the 3-date Rule for Finding Love After 50?

The biggest mistake women make, which prevents them from finding the right person for them, is staying too long with the wrong person.

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Personal Growth

December 24, 2023

7 Questions to Ask Yourself at the End of the Year

Here is your end of the year exercise. I never miss doing it myself and it works every time! Answer the following, in writing!

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Online Dating

March 27, 2023

Dating Hack: 5 Things You'll Learn From A Video Chat That You Need to Know

There are 5 things THAT YOU NEED TO KNOW that you will learn by setting up a video chat with a potential date…

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Communication

March 5, 2023

Make Awkward Talks Less Painful with this 8-Step Awesome Cheat Sheet 📜

Dating requires awkward talks about sex, STIs, kids, and monogamy. I have an 8-step cheat sheet to make them less painful and a little easier.

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Commitment

February 5, 2023

How to Have the Conversation to Establish Monogamy in 4 Easy Steps 👣👣

Never assume you're monogamous just because you're dating. By Date #3, ask if you both want the same thing before you get attached.

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