Primary Blog topic

Dating Challenges

View all entries
Age Gaps

August 20, 2026

5 Reasons Men Are Drawn to Older Women

I have coached daters for over 20 years, and one theme keeps getting louder every year. Younger men (and of course older men) are actively seeking out older women, and it is a real, growing part of the dating world. If you are a woman over 50 wondering whether you still have…

Read more
Sex

July 30, 2026

When to Have Sex While Dating: 6 Questions to Ask

The dating game after 50 comes with a lot of unwritten rules. The biggest one? The third date is when sex is supposed to happen. Maybe you followed that rule. Maybe you walked away from a promising new relationship wondering why romantic relationships that felt so real suddenly…

Read more
Dating Mindset

June 4, 2026

Why Is a Man Over 50 Still Single?

In my family, there is a famous story about my grandmother Sylvia, who came to the US from Poland in the 1930s. Sylvia was notoriously skeptical, untrusting, and frugal. She could spend hours in a store examining potential purchases and still leave with nothing. No decision came…

Read more
Compatibility

May 7, 2026

8 Things High-Caliber Mature Men Actually Want

As a dating coach, I hear it constantly. "Men just want someone younger." "Older men just want sex." "The older guys on dating sites just want a caretaker." I get why women believe this. The dating world can feel brutal, especially after a long marriage or years on your own. But…

Read more
Sex

April 23, 2026

Should I Have Sex on the 3rd date?

One of the biggest mistakes women make when they first get back into dating, especially after a divorce or a long dry spell, is having sex on the 1st date, the 2nd date, or following the famous "third date rule" on the long-awaited 3rd date. I’m not judging you. I understand it.

Read more
Dating Challenges

April 16, 2026

Where Are the Good Men?

I hear this every week. “Laurie, where are the good men?” "I can't seem to find any." "I don't think there are any good ones left." "All the good ones are taken." "I've been on the dating apps, and there are none there. Where are they?"

Read more
Sex

April 9, 2026

Sex Over 50: What Nobody Tells You About Desire

I am going to say the thing most women over 50 are thinking but not saying out loud: I am not sure I can have a great sex life anymore. Maybe you have quietly decided that the chapter is closed. Maybe the physical changes, the low libido, the vaginal dryness, the hot flashes,…

Read more
First Dates

February 12, 2026

4 Types of Questions to ask on the First Date

If you’re dating again after 50, the first thing to remember is this: chemistry is not the only thing that matters. You can have a good time, enjoy the small talk, even feel sparks on a first date, and still end up with a partner who is all wrong for the kind of life you…

Read more
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…

Read more
Trust

August 15, 2025

How Honest Should You Be on a First Date?

Let’s brush our teeth before we kiss, he said on our first date, implying I had bad breath! I was mortified. But I brushed my teeth, and we had a great first kiss. That was decades ago, and now we’ve been married 27 years. When asked how I knew he was the right person, I harken…

Read more
Confidence

July 31, 2025

Are You Undateable? 6 Things You May Not Realize

If you’ve ever secretly Googled “Am I undateable?”—first of all, hi, welcome, you’re in good company. Second, the fact that you’re asking that question probably means you’re not. Truly. Single women who are reflective, curious, and willing to assess their love life honestly are…

Read more
Sex

May 17, 2025

Can Sex Get Better After Menopause?

If you’re post-menopausal and dating (or thinking about dating), I want you to know: you are not alone, you are not too old, too dry, too rusty, and you are not done. So many women in their 50s, 60s, and beyond are re-entering the dating world and wondering with regards to sex……

Read more
First Dates

April 25, 2025

Fun First Date Ideas

First, let me just remind you, there will be no first date unless you have had a good time getting to know the person over text, phone call, or video chat, and feel that they meet your 3H criteria.

Read more
First Dates

April 3, 2025

Worst Date Ideas

Bad dates are the worst. We've all been on crappy dates and been wondering the whole time, when will this be over? I want to save you from ever going on a bad date again with some top tips for the first three, which are the most important!

Read more
Love

December 31, 2023

5 Strategies to Infuse more Romance

If you are looking for New Year’s resolutions for your love life, take this quiz! Are you showing up the way you want to show up? If not, this quiz will give you some very good ideas for improvement.

Read more