Maps are cool, but they don’t prepare you to walk the terrain. Richard cuts through the noise to what matters most: who you are, what you want, and why getting clear on both changes everything.

About Richard

Long form:

Most men re-enter the process of dating assuming that the sites and services out there currently will work for them rather than something they need to prepare for. They believe confidence will cover for the fact that they haven’t defined what they want. The simple truth is clarity always wins, in sales, in negotiation, and in love.

Richard Strother is a dating and relationship mindset coach. He works with men who’ve lost a spouse or been blindsided by divorce, though the clarity work he does is useful to anyone who’s discovered that “just get back out there” doesn’t prepare you for the reality.

In 2018 he lost his wife of 20 years. He eventually figured out what came next. He got back into the dating world and learned how to navigate it; then he wrote a book about it. It’s called Dating Doesn’t Have to Suck, and he means that literally.

He’s been in front of rooms his entire career. From his years of experience as a trainer at Apple, to working with individuals and groups as a coach. He’s comfortable, direct, and given the weight of the topics he covers (grief, identity, and what it means to start over), he’s surprisingly light hearted and fun to listen to.

Short form:

Most men re-enter dating without knowing what they actually want. Richard Strother has made a career of fixing that.

He’s a dating and relationship mindset coach working with men navigating life after loss or divorce — though the clarity framework he teaches is useful to anyone who’s ever swiped right and wondered why it still felt wrong.

In 2018, he lost his wife of 20 years. He eventually figured out what came next. Then he wrote Dating Doesn’t Have to Suck. Something that he means literally.

Audience First

I’ve seen enough interviews to know the difference between a guest who shows up for the audience and one who shows up for a promotion.

Your audience trusts you and I will honor that trust by being a guest who brings the kind of solid value that your listeners keep coming back for. The book will be there for those who need it; everything else tends to take care of itself when the conversation is worthwhile, and entertaining.

Talking Points

The Book – Dating Doesn’t Have to Suck

Dating Doesn’t Have to Suck is the no-bullshit field guide for men who lost a spouse or were blindsided by divorce and are trying to figure out who they are now — and what they actually want. It is also surprisingly relevant for those who are disenchanted with the current state of dating.

If you’re booking guests, feel free to grab a full review copy by clicking HERE.

It’s a protected PDF — watermarked, no printing.
(I’m surprisingly reasonable about excerpts. 😉)

The Emotional Traps in Moving Forward and Dating

1. Most men only get to grieve later

Between the social expectation to stay strong, keeping daily life on track, and no clean closure due to bureaucracy and logistics, most men don’t get to grieve until much later — and that delay has a cost.

2. Opinions are like assholes, everyone has one and I really need to like you to want to know about yours

Everyone has an opinion about  your process and how quickly it should play out. This is about the honest conversations we need to have with those people to preserve our relationships while protecting what we actually need.

3. Moving On versus Moving Forward

“Moving on” gets sold as the French Foreign Legion version — leave everything behind and don’t look back — but moving forward means choosing the parts of yourself that honor who you’ve become and facing what’s next with intention.

4. Sexual shame, what it costs us and how we face it

The mixed messages around sex in our society has led to a ubiquitous trend of shame when it comes to desire. That discomfort and the lack of distinction between, intimacy, erotic, sensual, and sexual undermines every conversation about all of it.
(2nd book content)

Fill a Void or Share a Life

5. How to tell what “ready to date” looks like from the inside

The desperation when someone isn’t ready is a stark contrast to the peace of someone searching from a place of sovereignty. It’s the difference between scrambling to find a gift at the last minute and recognizing the perfect one because you know the person well.

6. Being social matters more than we previously thought

The Harvard Study on Adult Development, Simon Sinek’s recent talking points around friendship, and the results of studies on loneliness and isolation all point the same core truth: getting social is key to a healthy and fulfilling life.

7. How men and women approach dating differently

Men are object/objective oriented: solve the problem, get the result. Women are contextually oriented — is it safe, does it hold up over time? Most early dating falls apart because we’re prioritizing the wrong things and trying to rush the results.

8. It’s okay to be a work in progress provided the foundation is solid

Building in phases is good, but you can’t build anything lasting without a clear plan and solid foundation. Knowing what you stand for, what you value, and your stability-to-novelty ratio is the foundation others can see, trust, and choose to build on with you.

Redefining Modern Masculinity

9. Modern masculinity made simple

Strip away the noise: masculinity is leadership — stability, personal responsibility and command of yourself above all. Leading by example isn’t a communication strategy, it’s the only thing that lands honestly and happens to be a deeply attractive trait.

10. The miserable standards of how men are portrayed in the media

From the Lovable Oaf, the Jaded Veteran, the Corrupt Professional, the Awkward Nerd, to the Wrecking Ball the persistent negative representations of men in media have been quietly shaping culture for a long time.

11. The practical definition of confidence

Confidence isn’t fearlessness or being unflappable — it’s trusting that you’re capable of handling whatever comes your way, and that’s a skill anyone can build.

12. You are worth far more than you think

Somewhere between childhood and graduation most men came to believe that their worth must be earned and is conditional — this conversation is about where that came from and why it’s wrong.

What Men Get Wrong About Dating

(These topics will be part of the 2nd book)

13. What most men get wrong about approach, meeting, and early dating

The specific, correctable mistakes most men make in the early stages — and why most dating advice makes them worse.

14. There are only four ways to actually meet people

Dating apps are just one option… let’s talk about all four, and why it’s not just about picking one.

15. Be who you are, rather than who you think she wants you to be

The performance of attractiveness is exhausting and ineffective. Authenticity is both the ethical choice, and the strategic one that saves time, effort, and trouble, now and over time.

16. You have one job: build safety and trust over time

Everything else is noise — let’s simplify early dating to its single most important task.

Media

Video Clips

Podcasts

Tendrils of Grief with Susan Ways – 45 min. (Mar 25th, 2024)
Listen on: Apple | Spotify | Website

Love & Dating Gurus with Dr. Dan and Industry Experts – 32 min. (Jan 19th, 2024)
Listen on: Apple | Spotify | Amazon | iHeart

The Unshakable Habits Podcast with Stephen Box – 56 min. (Nov 22nd, 2023)
Listen on: Apple | Spotify | Amazon | Youtube

Next Page Podcast with Laura and Todd – 61 min. (Oct 31st, 2023)
Listen on: Apple | Spotify | Acast

Bringing Intimacy Back with Dr. April Brown & Coach Kay – 32 min. (Oct 12th, 2023)
Watch on: YouTube

The Yakking Show with Peter Wright & Kathleen Beauvais – 29 min. (Sep 11th, 2023)
Listen on: The Yakking Show Website | YouTube Listen on: Apple | Spotify | Google

The Mountain Top Podcast with Scot McKay – 35 min. (July 27th, 2023)
Listen on: Mountain Top Website | Apple | Stitcher | iHeart Radio | Google

The Prime Life Project (with Daniel James) – 68 min. (July 4th, 2023)
Watch on Youtube | Listen on Spotify | Apple | Amazon | Tune In

The Crazy Over 40’s Life (with Caroline Brown) – 35 min. (May 25th, 2023)

What is Manly? (with Damian Andrews) – 93 min. (May 24th, 2023)

Unfiltered Discussions (with Brian Howard) – 60 min. (May 15th, 2023)

Sex Advice for Seniors – 42 min. (April 18th, 2023)

Bridges Bulletin – Old School Coaching For The Modern Man – 33 min. (April 7th, 2023)
Click here for Video | Click here for Audio

Headshot

Contact

Website: http://thewidowerswingman.com

Email: coaching@rstrother.com

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