December 2023

Which Dating Site is Best?

2023-12-08T15:14:51-04:00December 8, 2023|Articles|

Going through Facebook this week I came across a great variation to the very common question about which is the best dating site.  

The exact question was:  “Best dating apps.. with the least amount of creeps??? Haven’t been on a dating app since my early twenties..”

So let’s get to a real answer.  What made this variation stand out is the fact that it is very specific about a particular criteria that defines “best”.   

Dating Sites Are Like Forums

You can find a forum for every interest under the sun… just like dating apps/sites.  Whether it’s general interest, sports, video games or getting kinky there’s at least one dating app/site or at least a dozen forums for what you’re looking for.  Either way there will be all kinds of people… some are not really into it but want to observe, some are nothing short of fanatical, some want to sell you something, others are cool, well adjusted people who are just right.  

The biggest difference is that where dating apps/sites are concerned there’s money involved and companies want to stay in the black so for some of the smaller companies there could be some unscrupulous behavior.  That being said it makes sense that the larger and more well established companies (and more generic/general interest) have enough legitimate users to not need to resort to padding the user base with bots or fake users. Dating sites are a business and they only make money by keeping you along for the ride.  

So How Do I Avoid This?

The short answer is… you don’t.  The way you get the relationship you want is by understanding how the play the system to your advantage.  The dating sites want you to treat this as a “numbers game” and offer some resources which will tell you exactly what I will if you dive into researching it like you’re going for a master’s degree.  Play it their way and the house wins because either way they keep you paying for their service and if you win they’ll happily claim credit for your relationship.  Here’s the ultra-condensed version of how you succeed with online dating pretty much regardless of the site.

  • First and foremost above all other things you need to be abundantly clear on what you are looking for.  The rule I use with people is:
    • Up to 3 deal-breakers (these are severe, like I would, without hesitation stand up and walk out on an otherwise ideal date if this came out)
    • 5 ideal specific traits (and only five, this is not a job interview and if you come in with a long list or a vague set of notions you’re never going to meet anyone who fits)
  • Who you are, what you stand for, and what you are bringing to this relationship

With this knowledge you can begin to decide on what site has the best chance of finding the type of person you’re looking for.  If there’s a specific site for one of your top five traits then look there.  A couple of tips…

  • Use a search engine to ask the approximate number of users of the site you’re thinking in your area, city, county, or state.  While user data is not public the search engines can give you some general info as to whether this is a viable option for the area you’re willing to search.
  • New, smaller and niche apps/sites are going to have less people overall so on these sites be ready to be open and versatile.  These sites are also more likely to have bots or “padding” accounts.  More info to connect on is good and ask specific but open ended questions.  If answers seem odd, vague, or evasive then assume its a bot and move on.
  • Larger, well-established general sites are going to be all about getting very specific and standing out.  Be boldly and unapologetically you (this can take some work but it’s totally worth it). 
  • In both cases be ready to “play the long game” by being consistent while limiting interaction with the app/site to one to two times a day.  
  • Expect that a response to any outreach could take up to a week and if it leads to nothing that’s okay.
  • When a conversation does begin your primary goal is to see if this could be a friend (nothing more).  I tell everyone I help that the first date is “proof of life” and “do you vibe?”… that’s all.  It keeps expectations healthy and realistic.

The ability to pace oneself and keep expectations in check is a critical skill set to avoiding the hype and taking this journey in stride.

Just the Tip of the Iceberg

Dating has changed immensely in the past twenty years and I’d say even even more so in the past five years.  One thing hasn’t changed though… if you want to meet singles you need to go where the singles are and right now that’s online.  The sites/apps are businesses but by knowing how their systems work you can totally make that work to your advantage.  

Get clear, know what you’re looking for so you know where to look, pace yourself and manage your expectations and you’ll find some astounding results.  Need a hand? Reach out. I’m always happy to help.


Richard Strother is also The Widower’s Wingman.  After losing his best friend and wife in October of 2018 after 20 years together Richard decided to find a new path that put all the best of his skills to use.  After finding the most incredible relationship and helping several others do the same he started The Widower’s Wingman to continue helping men who’ve lost find their amazing and life altering relationships.

3 Things Black Friday Can Teach Us About Dating

2023-12-05T17:24:59-04:00December 1, 2023|Articles|

Yeah, I’m sure You’ve noticed it too… it was the first of November when I saw those words on one of my social media feeds.  

For those who don’t know the origin… “Black Friday” is the first Friday after thanksgiving that marks the official beginning to the full-fledged Christmas shopping season.  Traditionally it was the first day of the year where most retail store ledgers would go “out of the red” and show black marking a time of profit.  The ubiquitous sales were a cleverly designed ploy to encourage this trend of spending and get people into the shopping mindset and a push to clear out less popular stock (even if it was at a loss) because people would consider the higher ticket and more profitable items since “we’re already here and they have it in stock”.

Every year however this keeps creeping up a little earlier as do the Christmas decorations around retail stores.  Why?  Because many businesses are getting increasingly desperate for your holiday spending dollars particularly as consumers at all levels pull back on their spending a little more every year. 

If I’m all about relationships why would I be talking about this trend? Because there are thee lessons this can teach us about relationships.

#1 Desperation Spells Doom

We are animals and have instincts. Despite how much we try to repress or deny that fact we can sense fear and desperation even if we can’t articulate it as such.  Many of the “Black Friday Specials” especially the early ones can have an “ick” factor about hem that is remarkably similar to a bad date.  We feel it on a primal level when we perceive that the intent is not genuinely aligned with our interests.  

What does this mean in the dating world?  Avoid the “ick” by being 100%, completely authentic; by both knowing what You offer, are looking for and that you’re meeting them where they are to discover where you both align.  Mind games, manipulation and drama are for chumps and not a winning approach. 

#2 We All Love a Bargain

It may sound silly but getting a bargain makes us feel good.  In the brain a big bargain has all the same neurological markers as our ancient ancestors got from a successful hunt.  We ventured out from our caves (even if we do so virtually) and found a worthy and valuable prize and hunted it down and best of all we did this while minimizing our losses.  That’s amazing!

Here’s something else that’s true neurologically… what we gain through strife, struggle and loss we value that much more.  We are hard wired to avoid loss before we seek gain.  This is doubly true if we “settle” for something lesser.  

What does this mean for dating?  Well, for starters, know what you value and what’s important.  Be clear and vivid about exactly what that looks like and accept nothing less.  On the same token is is critical that you understand that this will take patience and effort, it might even “suck” for a little while and that’s part of finding someone that can’t live without rather than the bargain offered.

#3 You Don’t Need to Follow the Script

Black Friday was made to hype up the shopping season.  This is a script that’s meant to drive consumerism which while still alive and well is changing for a number of reasons which I’ll not get into here because I could rant a one hundred page thesis on it.  I can and will say that people and families by and large are re-evaluating priorities and how their resources are allocated; some by necessity but many because “stuff” has become more disposable and we tend to prefer something small and meaningful rather than “stuff for stuff’s sake”. 

So how does this apply to relationships?  Relationships have changed drastically in the past 40 years.  The old script of the nuclear family with the kids, and house with the white picket fence is no longer viable.  We’re told a lot about what a conventional relationship looks like and what’s “normal”.  Things like moving in together, everything should be fifty-fifty, and other such “conventional wisdom” is all claptrap.  Talk together, find out what works for both of you.  Align expectations, make sure that those directly involved feel heard, respected and valued and make your own script.

Beyond the Hype

Dating doesn’t have to suck and relationships don’t have to be hard and yes, women and men really do need each other because we all need connection.  You can choose to follow the script, conform, fit in but I rather doubt if you’re reading this far that’s worked particularly well so far (or you know and like me).  There’s another option available… it takes guts to get out there and be open and unapologetically authentic.  To defy “conventional wisdom” and seemingly risk everything can feel tough but when you find your people and reap the rewards of that choice, it gives you the power to write your own script and be all the happier for it.


Richard Strother is also The Widower’s Wingman.  After losing his best friend and wife in October of 2018 after 20 years together Richard decided to find a new path that put all the best of his skills to use.  After finding the most incredible relationship and helping several others do the same he started The Widower’s Wingman to continue helping men who’ve lost find their amazing and life altering relationships.

November 2023

Giving Thanks for the Gifts From Those We’ve Lost 

2023-11-23T18:19:19-04:00November 23, 2023|Articles|

Along with the cooler autumn weather comes Thanksgiving.  Here in Canada it’s about a month earlier but iI’m semi-convinced that’s because the leaves change here earlier (I know that’s not the case but it strikes me as funny).  This is typically a time for getting together with family and friends, to collectively look back at everything we have to be grateful for.

Holidays are generally difficult for those of us who have lost the people we hold most dear. It can be hard to be jovial and grateful in their absence.  It could be that we feel like we don’t have a right to be celebrating, or are frustrated by the audacity of a world that seems perfectly content to keep barreling on when our world has come crashing to a halt (or maybe a slow crawl).

Ultimately, on this Thanksgiving, I’d like to share something with You for which  I’m grateful  and hopefully clear a path to find this for yourself.

Parting Gifts

I’ve lost a number of very close people in my life.  Beyond my wife Samantha, I lost the man who, while not my biological father, was absolutely my father figure since I was 6 years old and from whom I learned so much.  My maternal grandparents were extremely close and a quintessential part of my upbringing and, while they are both gone, they were a big part of shaping who I have become.  With each respective loss I noticed something of them blossom inside of me, a parting gift, an aspect of them that I think  it is both my duty and privilege to carry forward and share anew.  It’s also worth noting that these traits are things that I admired in them and showed no exceptional aptitude for before their passing.  It is through my intentional expression of these gifts that I honor the, show my gratitude both to them and for who I’ve become because of them.

If you’ll indulge me, I would like to share with you the gifts I received from the loved ones I’ve lost.  I hope that in doing so that you might find similar gifts that those that you’ve lost have left within you.

I Am Thankful For:

  • my grandfather, Arthur Gould, who in life showed me the joy and levity of intellectual mischief and left with me an appreciation and ease with quotes, wordplay and a special kind of wisdom that comes with questioning the status quo.
  • my grandmother,  Phyllis Gould, who showed in life that patience and compassion were the key to success with people and being a classy badass is something one can be at any age.  She left me with a vocation to teach and an intuitive grasp of how people need to connect to what they’re learning
  • my best friend, partner and wife, Samantha Wexler ,who in life embodied integrity without compromise, unwavering determination, as well as the importance of connection and purpose.  She left in me an appreciation of art and the tapestry of stories, trends and causalities behind what we see (both in art and the world).
  • To the father with whom I grew up Michel Zeppettini, through whom I got to experience and appreciate great restaurants and food, see how businesses and financial mechanisms worked, and who never pushed me to change who I am fundamentally,  while always challenging me to be better.  His gift was an understanding of the complexities and systems behind the scenes which affords me a type of peace and patience I truly never previously had with such things.

I have wonderful memories of all these people which I will always cherish.  Each and every one of their passings is a loss for so many who knew them.  And yet I find within me these gifts with which I can move forward, share those aspects of who they were to help others just as they would readily have done.

A Question For You

Who have you lost and what have they left for you to carry forward?  What do you notice differently that they would have shown you?  What strength or subtle intuitive understanding have you noticed that you admired in them?  I believe we all get some kind of gift in that way from those that change the course of our life.  I’d love to hear about yours… I truly would and I invite you to reach out and share.  Even if it doesn’t feel very festive just now I wish you a Happy Thanksgiving and may you find the peace you need to get you through.  When you’re ready please reach out… I would love to know what gifts you’ve found from your loved ones.



Richard Strother is also The Widower’s Wingman.  After losing his best friend and wife in October of 2018 after 20 years together Richard decided to find a new path that put all the best of his skills to use.  After finding the most incredible relationship and helping several others do the same he started The Widower’s Wingman to continue helping men who’ve lost find their amazing and life altering relationships.

A Dater’s Guide to Being Interesting

2023-11-16T18:11:53-04:00November 17, 2023|Articles|

Chris sat at the little table in the bustling coffee shop, his palms sweating. He had the sensation that his brain was attempting to swim in the whirlpool of his own thoughts. It was a first date with a lovely woman named Sandra… at least the one and only photo on her dating profile gave the impression she was pretty and her texts were kind and cheerful. Chris lamented as he thought back over his own texts. They were by his estimation short, clumsy at least by comparison to her eloquent and descriptive replies. Of the torrent of racing thoughts the most distinctive were “What am I going to talk about?”, “What if she thinks I’m boring?” and “What if she thinks I sound like an idiot?”

It was the tinkle of the little chime at the door that broke Chris’s train of thought as he looked up and saw her step in accompanied by a refreshing gust of fresh air from outside. It seemed as though the world moved in slow-motion as he took in the details of her face. It was definitely her but the photo did not do her justice… there was a definitive air of elegance and her dignified features only served to accentuate that. Chris saw nothing of the coffee shop, only her and marveled that she was here for him and when the sheer euphoria abated enough for his sense of self to come back to him he realized that he was standing though he could not recall requesting his body to do so.

She all but glided over once she recognized him. Her smile radiant, her hazel eyes were keen and kind.It seemed as though someone pulled the stopper and the whirlpool of thoughts had drained out because now Chris couldn’t think of anything at all… Instead Chris feels like this.

Photo from: Addams Family Values – ©1993 Paramount Pictures

Let’s Take a Moment to Reflect

First things first… Chris may not be a fashion model but he’s not Quasimodo either.Chris’s big problem is he’s psyching himself out, a common problem at every stage of dating and worthy of it’s own article (or seven, and they are coming).Let’s deal with Chris’s more immediate concern of feeling inadequate and dull.As our scene here is paused let’s gently place three reminders in Chris’s head:

  • This is not a TED Talk, comedy set, or a trade show presentation… so it’s not all on him. This is the time to relax and be in the moment and go with the flow.
  • Many of us have a tendency to put all our hopes and dreams in to one basket. Suddenly our entire future and all potential for happiness relies on this one encounter going well. We must do anything and everything within our power to avoid the cataclysm of doom, fire and destruction! That’s us psyching ourselves out again; we do it with job interviews and dates and all kinds of events. Deep breath, take a mental step back. Coffee house, nice human sitting across from us… Now all we have to do is smile, say “Hello”, and make a friend. It really doesn’t need to be any more stressful than that.
  • Having been a very successful trainer there were two things that were critically important. The first is “Let them steer the bus”… for training to be helpful and relevant it has to go where the client needs it to. The second is W.A.I.T. (Why Am I Talking?). Listen to what the person you’re training needs, acknowledge and respond to their needs

Let’s Go Back to Chris

After a simple “Hello” and exchanges of “it’s so good to meet you”, Chris sits down, takes a deep breath and embraces the emptiness inside his head and with that the pressure releases. What was supposed to be a simple coffee turns into four hours of delightful sparkling conversation as Chris listens and learns about Sandra and her various travels despite, it turns out, having grown up less than a mile from each other but they didn’t go to the same schools. By the end Chris felt delighted… perhaps he’d leave the car parked and just float home. They would meet again next week and Chris was already looking forward to that time.

Wei Wu Wei (Do Without Effort)

For anyone familiar with Alan Watts or Taoist principles this is one of those weirdly effective things that flys in the face of conventional thought. The ability to relax, be completely authentic and listen shows that we are genuine and engaged in real meaningful exchange. This in turn makes us both interesting and attractive because there is a safe space in which everyone is Heard, Respected and Valued. Water will flow where the resistance is least and if we get out of our own way it will flow naturally. As for whether this person will be the right fit… for that you’ll need to follow the flow and see where it leads.

I Like my Online Dating Like my Steak… Well Done

2023-11-16T17:45:16-04:00November 7, 2023|Articles|

Greg sat there with a hot mug of coffee and a mountain of determination. He was going to look through as many profiles as he could on the dating site he’d recently signed up for.  His search found over two hundred matches, but the more he looked, the more his hope started to dwindle.  Row after row of generic placeholder images where a photo should be with simply a username and age underneath was what he saw.  For a fleeting moment, the thought of a cemetery popped into his mind, with its rows on rows of low grey stone and brass plaques noting the presence of a person, but with no character or charm to showcase who they were.

“I’m not shallow,” thinks Greg, “Looks aren’t everything after all,” and into the profiles he dove.  Profile after profile served to etch the words in his brain that became so recognizable they needn’t even be read… “I’ll tell you later”.  To be fair, about half the profiles had some form of bio, but Greg starts to notice a few trends.  “I’m the quintessential Sagittarius,” and similar proclamations of a zodiac sign as though it is supposed to convey everything one needs to know, the many mentions of morning yoga, how their pet is the centre of their life, and lastly “a glass of wine in the evening,” became so commonplace that he thought he was reading a new version of the Stepford Wives.

Now Greg found himself with a sense that something in general was wrong, and after looking at several more profiles it hit him… these are  “fast food” style profiles. Generic..and common.

What’s wrong with fast food? 

Fast food and large franchise restaurants have their place.  They’re comforting because they’re familiar.  We go there, not for the outstanding quality or unique experience, but because it’s easy and we know what we like (because we tend to like what we know)! 

Dating isn’t about blending in but standing out

Greg, however, is a chef and has been in the restaurant business for a while. Suddenly it all becomes clear and he sees how online dating has the same essential truths as the restaurant industry. 

He thinks about his own profile and how instead of being ubiquitous and familiar he needs to treat this like a stand out local restaurant.  Breaking it down Greg sees it like this:

  • Even before you step in the door, a stand out restaurant will showcase a style of decor to impress upon prospective customers what they can expect within.  So the photos on my profile are not just about what I look like but need to give an idea of what to expect of me as a person.
  • Once inside, how customers are greeted should be welcoming and reassuring, leaving no doubt that this is the place for you. 
  • Just as the photos and greeting set the tone for the restaurant and the experience to come, my profile needs to set the tone that is consistent with who I am and the overall kind of experience I bring. 
  • The next logical step on this journey is the menu, which should showcase the chef’s personality, style and skill.  If the content of my profile is my menu, it needs to showcase only the best of me and what specific kind of experiences I offer because I enjoy and do so naturally.
  • The timing of service counts. No customer likes to wait too long for food or service. People are generally really understanding of issues if they understand what’s going on, so being up front and transparent is important.  You don’t need to be a slave to a dating app but you should be mindful and respond in a reasonable timeframe, even if just to let people know where you’re at and where they stand. If it becomes clear that they’re looking for an experience that  you are not comfortable offering, don’t be shy to let them know that this may not be a good match.
  • The food needs to always be the best you can offer for what was described. Does it live up to the experience that was described?  Does it make you want to come back for more?  If someone enjoys the experience enough to return then the true test begins. 
  • Can you deliver on the experience again and again? Can you do so consistently?  If you’ve been authentic, honest and relaxed then this should be a piece of cake.

A stand out local restaurant doesn’t just mean Michelin-star winning French bistros.  We’re talking about everything from the family owned dessert shop to the classic Italian trattoria, the teppanyaki grill to the local sports bar with the wings you can’t get enough of, to the truly original medical themed diner (Heart Attack Grill) or a local dinosaur themed geek-friendly teahouse (Thésaurus Thérrarium). Each one of them has their unique style, character, identity, and delivers consistently on their experience and attracts  people who are comfortable there.

What’s on your menu?

There’s nothing wrong with astrology, yoga or a glass of wine but restaurants that stand out don’t just say “steak”.  Like any menu item meant to tempt, be specific and descriptive with your profile and stand out by calling out your fellow connoisseur. 

“A glass of wine” as a description pales in comparison to “a pleasantly moderate glass of German gewürztraminer” both in charm, personality and the opportunity for a recommendation or discussion.  Maybe the wine is merely your ritual to celebrate those precious blessed moments of peace away from a “hair on fire” kind of busy life, and there are many who would prize sharing those moments of peace over a drink.  

Being “into sports” is vague, almost evasive, where a well placed “Go Birds!” or “I like watching Lightning score twice” will let fellow  fans know where you stand and could lead to anything from playful teasing about rival teams to adjacent seats in your home team stadium for as many games as your respective schedules permit.

Wrapping it up (to go)

As It goes with restaurants, so it goes with dating! Success boils down to distilling your identity into a tempting and friendly opportunity, and what sets you apart from the crowd are these very reachable things:

  • Be 100% authentic, and 
  • Stand out to the people who will be delighted by the experience you consistently provide because it’s simply about who you actually are! 

Make the effort so that the people around you feel heard, respected, and valued and you’ll stand out even more in all the right ways online or in person. Whether you’re a sports bar type of person, a Michelin-star winning french bistro type of person, or a family owned pizzeria type person,  then be that, unapologetically (says this unapologetic Canadian)!  It’s easier than pretending to be something you think people want, and infinitely more attractive, because, in the end, everyone’s attracted to people who know who they are.

October 2023

What We Can Learn From a Good Old Fashioned Haunting

2023-11-16T17:43:19-04:00October 31, 2023|Articles|

As it is the season for all thing ghastly, ghoulish and ghostly,  I share with you a haunting tale of  a man forced to face his own demise.  The hero of our tale is not a particularly likable man for he is miserly and bitter.  His best friend unfortunately died several years ago and it affected him. His work and his money account for most of his attention and very limited social interactions are limited to a couple of people in his employ.  

The day in question was much like any other.  He walked home after closing up the office, the chill evening air clinging to him though he paid no attention to it.  Once home he went to his room and got a fire going in the grate and had a simple supper in the small room he chose to sleep in, despite the house being very large.  Dozing off in the chair in front of the fire, the remnants of his dinner in a small pot next to him, he was roused by a terrible sound…

Wait, You say…this sounds kind of familiar!  No doubt it would,  as the tale of Ebenezer Scrooge is an instantly recognizable classic around the world. Why then would I bring up Charles Dickens’ most beloved Christmas story around Hallowe’en?

When I was young I was told that the Hallowe’en tradition of dressing in scary costumes and visiting our neighbors, friends and family stemmed from the belief that it was the night where the veil between the spirit and earthly realms runs thinnest, granting the opportunity for all manner of things made of spirit and spite to come and spread mayhem and malice —  so we humans would dress ourselves up in their image and wander around among our friends and neighbors to frighten away the malicious spirits, or to trick those spirits into believing that these places were already taken and that they should look elsewhere. The treats would simply have been little snacks or tidbits as would have been customary as the simplest form of civility and basic hospitality.

It is where these two stories meet that my point resides.  We as humans have a natural inclination to chase off that which we do not know or understand.  We go to great effort to dispel or deny those things that make us uncomfortable… as Scrooge protested to all but the last ghost who visited him.  While Scrooge’s was an unwelcome haunting, with extreme prejudice, it came to change him in the most important way.  His supernatural journey taught him what Hallowe’en was originally supposed to teach us… which is the same thing that the Harvard Study of Adult Development (which began in 1938 and is still ongoing)… the quality of our life is directly related to the quality of our relationships.

Scrooge was, thorough no choice of his own, thrown headlong into fearless review of his life, made to see it from an outsider’s perspective.  It was a harrowing experience because doing so is uncomfortable, humbling, and challenges the ego… much easier to “chase those ghosts away” and live in peace and comfort.  Some of us choose to face such discomfort, to set the ego aside and allow ourselves to be willingly humbled so that we might find a deeper sense of peace and a more connected way to live, much as Scrooge did.  

To find the truth at the core of ourselves and nurture it out into the light and share it with the people around us leaves  us lighter and free… free from being haunted by shame, loneliness, isolation and all forms of “spirit and spite”.  The more I see of the changes in our world these days the more I believe this is not just prudent, but necessary.

We are being haunted by some pervasive lies and assumptions; one such lie is that we can’t trust each other and that we must be independent and self-sufficient at all costs. Another lie is that we must “take sides” and only one side can be right and just and damn all who think otherwise because they must be “against us”.  This is at its core the very kind of “spirit and spite” we dressed up to chase away! 

We all want a better life, a better world but ultimately this comes down to a simple core idea… coming together and chase away those things of spite and malice that would divide us.  Celebrate together and embrace the diversity of our strengths and ideas.  Perhaps you’re wondering “How do I start?” and the answer is to choose to look at your past, present and what kind of future that would bring… by the sole power of your own spirit. Be fearless, challenge the ego, look at your life to find a purpose and path that moves you.  You’ll be amazed at how much strength and compassion you’ll find within your community when you’re part of chasing off the “spirit and spite”.  This is how we make the world a lot less scary.  

If you’re not sure where to start or need to talk about it my door is always open.
Why not book a free call?

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