The Secret To Having Fun While Dating. It’s Not So Secret…

happy woman wearing red sleeve kissed by her husband

Anna is a client who needs a hug (or three).

She’s 46, slim, attractive, successful – my typical client – but there’s a sadness about her. Maybe you can understand.

Anna didn’t picture her life turning out this way.

I mean, she always assumed she’d live up to her potential – the good grades, the nice home, the international travel – it’s that when she imagined her life at 46, she naturally assumed she’d be married with kids.

At this point, she’s accepted that the kids’ ship has sailed – she’s cool with being an aunt – but she still doesn’t see how all of her friends got married and she didn’t.

When Anna traces back the timeline, it becomes a little bit clearer:

She was just having fun in her early 30’s. That’s cool. Everybody was.

When Anna finally got serious about a man in her mid-30’s, he turned out to be the wrong guy. Which would have been fine.

Except she spent 3 years with him and 1 year mourning his departure.

After Anna finally got her head on straight, she decided to focus on the things she could control, the things that gave her joy, the things that couldn’t hurt her:

Work. Friends. Hobbies. Home. Family. Work.

So that’s what she did. For 6 years.

She put her head down, closed the door to love, and convinced herself she was happy.

Except she wasn’t.

It hurt her to admit that.

She wanted to be so strong.

She didn’t want to acknowledge that she wanted love, missed a man’s touch, cherished the idea of sharing a life with someone.

Any of this resonating with you?

After reading my materials for a year, Anna finally decided to take action.

She started with Why He Disappeared, graduated to Believe in Love, and eventually signed up for six months of Love U Masters Coaching.

Of course, Anna is one of those “most-likely-to-succeed” types.

She’s a good student, she’s extremely earnest, and she wants to get her gold star for a job well done. Most of all, she wants her investment to pay off.

Who can blame her?

Believe me, I want Anna to fall in love within the next 26 weeks as well.

But here’s the problem:

Anna is so intent on getting this right that she’s having about as much fun as someone studying statistics in order to get a math requirement filled for college.

Her instructions are no different than the ones I’ve offered you here:

  • Get online for a half-hour each night.
  • Respond to men using the methods from Finding the One Online.
  • Update your favorites list and reach out to one new guy a day.
  • Schedule 1 or 2 phone calls and 1 or 2 dates per week.

Yet week after week, Anna reports back that she hasn’t had time, hasn’t had the desire, is completely dispirited, wants to give up, is considering life as a nun.

She starts to cry.

I feel terrible.

I give Anna the virtual hug, the pep talk, the metaphors that allow her to come around to my way of thinking.

She momentarily feels better, but always falls back into her own patterns.

Her beliefs:

Dating isn’t worth it.
Dating is a waste of time.
Dating causes pain.
Dating is too much work.

Well, if that’s the way Anna feels, consider how that will dictate her results.

She will dread dating and avoid it as much as possible.

She will find flaws in men’s profiles so as not to have to engage with them.

She will take a long time to reply to other men because she’s too “busy.”

She will take any form of rejection personally, even though it’s not personal.

She will use the ups and downs of dating to justify why she doesn’t want to do it.

And there you have it: an airtight negative feedback loop. A self-fulfilling prophecy if there ever was one.

But it doesn’t have to be this way. Not at all.

Dating is supposed to be fun!

You see, dating is supposed to be fun!

Really. It is. I swear.

And if “fun” is the last word you’d ever use to describe dating, I’d like to introduce you a recent Love U student, Monique.

A month ago, Monique was down in the dumps. She’d gotten hurt by some guy, her self-esteem was down, and she was feeling really negative about men and dating.

As I was writing today’s newsletter, she emailed me this.

“I forgot how much I love dating! You get to meet new people all the time and never know if there will be a connection or not. This round of dating I’ve been to the best Indian restaurant in Seattle, the Seattle Underground tour, had a spontaneous picnic on at Golden Gardens after a long walk on the beach, went to my first sock hop, Smash Putt (Putt Putt on crack), Bollywood dancing, numerous other meals, I’m now taking dance classes, Speed dating, and I’m sure I’ve forgotten a few of the others.

I don’t worry about who is going to pay. I don’t worry about kissing them. I don’t worry about if this is my future husband. I just want a good conversation and a time to get to know another human being. If things click, awesome! If not…Oh well! There are PLENTY of men out there.

Once I changed my mindset about dating I realized this is the most fun I’ve ever had. I know it can get hard out there, ladies, but if you just go and have fun without a bunch of crazy expectations you will look forward to dating.”

Seriously. I couldn’t have written something better myself.

Monique is the same exact person she was a month ago.

Seattle is the same city it was a month ago.

Men are the same as they’ll ever be.

And yet suddenly, this one 36-year-old woman is having the time of her life.

All because she chose to change her mindset.

I can’t say whether you’re like Anna or whether you’re like Monique.

Both are readers and I am committed to both of their successes.

But I think it’s obvious that Monique’s attitude is not only healthier for her, but objectively more attractive to men as well.

Men love happy women, confident women, and women who are not remotely worried about whether this date is going to result in a marriage proposal.

Take the pressure off yourself. Flirt with a bunch of guys online. Go on a date or two each week with no set of expectations. Commit yourself to simply having fun with the process.

Next thing you know, you’ll have men lining up to be your boyfriend.

Sounds like fun, doesn’t it?

If Monique’s story sounds like a minor miracle – as if I put the words into her mouth – let me assure you, it’s no miracle.

This is the kind of thing that happens every day in Love U.

Not only are hundreds of smart, strong, successful women getting advice from yours truly, but they’re doing it at a FRACTION of the cost of private coaching.

Click here to learn more.

And in case you weren’t familiar, Love U is my comprehensive, interactive, affordable relationship mastery course that teaches you everything you need to know to date with confidence and make smarter relationship choices that last a lifetime.

You’ve gone long enough without a man who treats you like gold and wants to commit.

Now it’s time to get him.

Warmest wishes and much love,

Your friend,


P.S. How well does Love U work? Well, let’s just say I get a lot of emails like this:

Hey, Evan

I’ve got a boyfriend (as of last night). I was on OK Cupid for six weeks and have just pulled everything down. Six weeks. I was with another coach for years. Literally.

Thanks very, very much.


Lexi took action. She joined Love U. She got results in six weeks.

Wouldn’t you like to be next?

Join our conversation (7 Comments).
Click Here To Leave Your Comment Below.


  1. 1

    There is a huge difference between 36 and 46, Evan. You are correct that men and women prefer to date fun, creative, open, warm, caring people. However, I understand Anna too well. At 36, you still have that little window for the dream. At 46, one is closer to 50. I would tell her what I tell friends, “Focus on what YOU want and if its not fun, go to the next” As you have said, one needs to actually make the effort and keep going. The value is that hopefully one knows oneself better. This makes it easier to weed out those who would be unsuitable, but it makes dating a more choosy process from the beginning. Whereas, I had weekends at 36 where I went on 4-6 dates, at 46, being more choosy means half that. I had fun…its just a more selective process.

    At 46 (or 42+), I might consider shifting the emphasis to deciding which one is the right one vs getting dates…but sensing the reluctance on Anna’s part to go through the process, that is a challenge. Its not a a quantity game, assuming the eligibility pool goes to 10% or less. Its about building clarity around the process and being able to weed out, which then offers the confidence to have fun on a date. She may have had an eligibility pool of 8 at 36, this pool will now be 2-3 at 46, but it is certainly achievable. As we know, it only takes one.

    Thank you for all you do!!!

  2. 2
    Mz. White

    I completely agree with the previous poster that there is very big difference between 36 and 46 – I think dating coaches need to recognize that. At 46 its about getting the dates and if you are a high quality 46 year old you are all the things Anna is but you can’t get the dates. I am at successful 50 year old woman who looks like I am in my mid 30s and I act like it too. When I go out I get hit on my men in their late 20s to mid 50s. When I tell them my age they accuse me of lying if I actually show them my ID, they freak out and back off. If I don’t tell them they chase me around and when then find out they disappear. When I am on line and my age is apparent I get NO dates except from those at 70- years old men and boys looking for sugar mamas. I am fun and I am positive but its not about going on the dates its about getting them at this age. men who are players and scam artists also target women at this age range and pull all kinds of crap because they know they are vulnerable to this and I hate to say it if you care and have been alone for years you become more and more depressed or desperate. No matter how hot, rich or fun you are. And I believe I know why this is. Men who are high quality around the same age or even a little older (educated fun etc..) have their choice of women. Also, many have waited to settle down and have kids. All things being equal they will choose a younger woman every time and that is just a fact of life. Human DNA is hard core encoded to be this way. There is also a lot of science behind it as well. Now if your story was reversed it would bode a lot more credit to your method working but you need a different method for women who can no longer have kids and you need to be honest about that. I challenge you to interview a bunch of men while posing as a woman in her late 40s and see how well your methods work then. I know I read almost all your books and tried them all. You will find a completely different situation. Monique can get the dates per week because she is pulling them in. Anna can not and her sadness, if I had to guess, isn’t so much about the fact that she can’t have fun – its that she can’t get to that point and you are pushing her to believe its something wrong with her. Its not. Its something wrong with the world. Someone needs to help us older women find men who are age appropriate. – I want someone to match me., and it can’t be the same old answers we are getting over and over. Its not right. I feel bad for Anna, Please help her and by proxy of that help the rest of us.

    1. 2.1
      Evan Marc Katz

      Mz. White – if you pay close attention to my site, my emails, my blogs, my podcasts, you’ll see one thing: HALF of my clients are over the age of 50. MANY of my sixtysomething clients have more active love lives than clients in their thirties. So while you can shake your fist at the “same old answers,” I find that the more productive solution is to make the best of your situation, at any age, regardless of where you live. Feel free to apply to Love U if you’d like to implement the advice that you’ve absorbed thus far. It really does make a difference when you hear from 15 women on each weekly coaching call who are out there, making it happen successfully.

  3. 3
    Mz. White


    My apologies as your response is coming off a bit defensive. That was not my intention, however I respectfully disagree that I am “shaking my fists” I wish I had the time for Love U but my work is demanding. Which is why I read a lot. I take exactly the approach you outline in dating with out heartbreak and while it might not be your intention this response feels a bit like victim blaming. I read a lot. A lot of psychology books and dating books including yours. I read your news letter, which I love and in fact I thought about hiring you at one point privately to match my work schedule but your books are really good and you are busy. I do make the best of my situation and I travel quite a bit for work and enjoy my life – All I am asking you to do is to please look into the data, maybe take a survey and notice the pattern – It might vet you something new. Your work is great and I feel that if you were to put effort into this area what you might find is older women have a different problem. We need to understand that while not impossible they should set their expectations differently and that its going to take a longer period of time to find “the one” otherwise it drives the sadness we feel as women getting older in that we are doing something wrong or that we are not wanted anymore. Quite frankly we could be doing everything right. I am asking you to please not ignore here is that there truly is a lack of dates for women at 45+ on line. Its not about an active love life – its about meeting a quality man that wants to commit and for that the pool needs to be bigger or older women need to wait longer. Or have more approaches. I have specifically noticed this after covid as I can’t travel that much and “be out there”. So my “active love life” is now restricted to on line and if one is restricted to the same dating pool the pool dries up when you are knocking the players off. This was not meant to be an attack it was simply an ask for a talented coach with a big audience to look at a big problem and maybe just maybe notice it might need a different approach or set of enhancements for women who are older to offset the lack of dates they are able to attain. Would it really be so bad to look at it from a different perspective Evan? Ask your wife – she knows your stubborn by your own admission (yes I do listen to your pod casts) 🙂 – Much love and light!

    1. 3.1
      Evan Marc Katz

      Mz. White, I appreciate your feedback. Really, I do. The gap between us, as I see it, is as follows:

      1. You really have no idea what I do with women 45+. You’re not in Love U. You haven’t gotten coaching from me. You’ve read and listened to some stuff and have determined that my advice doesn’t work for women 45+.
      2. What you’re really saying is that things are rough for YOU. And I believe you. And I’ll validate that things are harder at 45 than 35 and harder at 55 than 45, etc.
      3. What you seem not to have considered, however, are two things:
      a. I’m not “ignoring” the lack of dates for women my age and older. It has literally been my job for SEVENTEEN years.
      b. You may find this hard to take but it’s true: I know more about this than you do. You only have your lived experience to guide you. I’ve been in the online dating accounts of probably 1000 women to see what they experience. As such, I have a much bigger sample size to draw upon than you do from your own life.
      c. You seem to think that older women need a “different” approach. Again, that comes from YOUR experience. In MY experience, older women and younger women – while dealing with different dating populations – are well served to do the same exact things. Because my advice is based on “effective/ineffective” not “right/wrong”, there are, indeed, best practices for dating that transcend age. This is outlined in great detail over 26 weeks in Love U.
      d. You want to believe that you’re doing everything right so someone like me has to come up with something special for you. I would challenge that, based on only the above. There’s only one thing different for older women – fewer men. But since I can’t do anything about that and you can’t do anything about that, there’s little value in complaining about it. You just have to make the best of your situation. Which involves the same advice – but, as you said, a little more patience.
      e. If you want to get a different result, don’t just read psychology books. Do something different. You say you don’t have time for Love U? Love U is 5 minutes of video per day. You say you want a different result and a supportive environment of women your age? I do group coaching calls every Tuesday and Wednesday to answer your pointed questions live on Zoom.

      Long story short: I appreciate your readership and your candid feedback. But what I know as a coach is that when I hear a complaint (about me, about men, about the world at large), there is an opportunity for growth. I sincerely hope you take it – otherwise it’s gonna be a lot more reading and complaining…with the same exact results as you got before you did all the reading. XO

  4. 4

    I want to acknowledge and affirm Mz. White. Agreed, you have data and the experience of almost two decades to back you up, Evan. No argument.

    However, I am happy to say that after Rori Raye, you, Barbara DeAngelis, John Gray, shamans, priests, rabbis, weekend retreats…the answer is the same…find a man who can both appreciate and acknowledge you and who shows his worth and commitment over time. Of late, I feel Steve Harvey’s methods have worked best for me…its a bottom line approach that has given me relief. This stuff is simple.

    When one is already confident and successful, it becomes about the weeding out process of getting to what is happy, healthy, authentic and real. I delete those who only text, have no interest in getting to know me, and/or need me rather than want me. Not about looks, height, weight…a man goes in and he can either get there or he can’t. Look for red flags, steer clear, stay positive, keep yourself as healthy and beautiful as you can and roll the dice. Many men just want a part time girlfriend or “buddy” and its easy to see. And don’t be discouraged if other women have made it easier for men to be lazy…we can set the pace. If they want you, they will step up. You are quality. And quality takes investment.

    Again, thanks for all you do!!! Keep us posted on Anna…I am rooting for her and for all!

  5. 5

    Mz. White

    The problem for older “high quality” women looking for “high quality” men of a similar age is that if your a busy type of woman whose work is the Center of your life, then usually the man you want is the same way. However most of these men are either already married, or else they’re divorced, but they’re probably looking to date either what they see as a wife type – someone who takes them away from their work and into home life, or else they’re looking for a fling with a younger woman. Basically many will be looking to seperate work and the romantic so they’re not looking to date someone who reminds them of work 24/7. Which is basically the opposite of what those types who want those age and “quality” of men are.

    While I’m sure that men who meet those women’s criteria and who would date them exist and are all over the place, those men also probably have a pick of women they want, especially from among the “high quality” women who seek them, so they’re unlikely to appear in high abundance on online dating sites.

    I don’t know for sure but I’m guessing Evans advice is either going to be to expand your definition of “high quality man” or else content yourself with the vague chance you might stumble on the needle in the haystack.

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