Should I Keep Trying to Find a Better Boyfriend?


Dearest Evan,
Wow! Thanks for helping me grow! I have a constant desire to UPGRADE. I relate it to a Jennifer Aniston Syndrome. She had Brad Pitt, so where could she go from there? She found someone funnier, taller, cooler, younger, etc. I find myself doing the same and now I am getting depressed from the lack of potential upgrades. I feel like I have set myself up for disappointment.

My ex-husband was the kindest and most romantic man. He worshiped me and he was a doting father. In the end, he was a weak cheater. How could I upgrade? I found a wealthy exciting man to date, son of a billionaire. Well, he turned out to be a playboy, of course. After a year of celibacy I met my latest man, my tallest, youngest, sexiest man. We became best of friends because we had the same exact taste in music, fashion, food, books. We joked that we were twins despite our age difference. After years of marriage and celibacy, the sex with my tall man was the greatest… But, I realize he is not leaving his drinking and player ways when he is out with his buddies. Now, I see every man under 6’5” as short and unattractive and boring. No one can hold a candle to his height and sex. I feel like there is no upgrade and yet I cannot be with a young player who drinks. Please advise. —Ultra


Actually, I think it was Pitt who decided to upgrade to Angelina, but let’s not quibble. Hollywood is notorious for its insecurity and one-upsmanship, so let’s use it as the model for what NOT do in dating.

Next, kudos to you for identifying the source of your discontent and for being brave enough to write in about it. Too bad you can’t seem to make a rational decision given what you already know.

Choices don’t actually make us happier; in fact, the more choices you have, the more paralyzed you become, and the greater your level of dissatisfaction in your life.

I’m hoping I can help you abandon this foolish idea of “upgrading.”

First of all, pick up a copy of Barry Schwartz’s The Paradox of Choice. This book IS the reason I’m married right now.

The two-sentence log line is that choices don’t actually make us happier; in fact, the more choices you have, the more paralyzed you become, and the greater your level of dissatisfaction in your life.

Sound familiar?

Schwartz divides the worlds into satisficers and maximizers. You and I are maximizers. If we have 95% of what we want, we’ll continue to look for 98%. We will not rest until we find it.

The irony is that satisficers are happier. They understand the paradox of choice. They know when there’s the illusion of greener grass and choose to stay on their side of the fence. They appreciate what they have and don’t spend any time comparing it to what they don’t.

Satisficers will say, “He’s cute, he’s smart, he’s financially stable: I’m keeping him.” Maximizers say, “He doesn’t like salsa dancing. He’s not 6’5. He doesn’t earn $300K/year. I’m dumping him.”

Satisficers get happily married. Maximizers hold out for the perfect mate and remain single — or, if they find love, continue their search for “better.”

Except better isn’t really “better.” And the cost of your search is greater than what you end up gaining.

After I read The Paradox of Choice, it was like all the light bulbs in my head went off at once, illuminating how I could be happier.

Instead of spending six weeks and ten hours researching flights to Florida to get the perfect redeye, with the shortest layover, at the lowest price, on my favorite airline, I bought a flight within a half hour.

No, I didn’t get airline points. Yes, I paid $54 more. But I saved myself TEN HOURS of time and frustration. These are the tradeoffs that smart satisficers are willing to make when they do cost-benefit analysis.

Next, I bought a camera in ten minutes on Amazon. Why? Because I’m not a photographer! I don’t know about pixel ratings and fancy lenses.! I wanted the best point and click for the most reasonable price. I got a Canon Powershot and have been perfectly happy ever since.

I also ended up getting married in 2008. Instead of comparing my girlfriend side by side with every woman I’ve ever dated — some sort of Frankenstein monster that never actually existed — I chose to focus on one thing: how I felt when I was around her.

Did I date younger women? Sure. Thinner women? Check. More educated? Yup. Wealthier? Absolutely. Better aligned with my politics and religion? Absolutely. And even though my wife fell below my high water mark in all of those categories, I still married her!

What’s wrong with me? Did I just settle? Am I telling you to settle?

For god’s sake, no.

Most people are irrational and make bad decisions. You don’t have to be one of those people.

I’m telling you that the things I compromised on don’t really matter.

I’d dated younger, thinner women — who didn’t make me happy.

I’d dated more intellectual, ambitious women — who constantly criticized me and broke up with me.

I dated women who were liberal Jewish atheists — and it didn’t mean that we were a great couple. It just meant we were alike.

So, Ultra, I hate to tell you but height doesn’t matter in 40 years.

Sex matters, but it only has to be good, not great. If you have similar libidos, tastes and the desire to please, you’ll be just fine.

Attraction matters, but good attraction doesn’t mean squat if he’s going to cheat on you or never wants to be married.

Look back on your life. You see how well it works when you compare every guy’s most amazing quality to the next guy?

It doesn’t.

Which is why your next steps should be easy.

Read The Paradox of Choice.

Understand intellectually that everything I’m telling you is true and that you ignore it at your own peril. Most people are irrational and make bad decisions. You don’t have to be one of those people.

Schwartz talks about a study where people would rather make $100K in a neighborhood where everyone was making $50K than make $200K and live in a neighborhood where everyone was making $400K.

That’s irrational.

People would rather make less money overall, as long as they make more than the people around them. That’s f-d up, don’t you think?

Next, stop comparing men side by side as if there’s some composite man who has all the great qualities of all the previous men.

There’s not. Pass up one guy who could be cuter and you’ll find yourself with another guy who could be a better communicator. It’s all trade-offs.

When you’re ready for the real deal, choose a man who makes you feel safe, heard, and understood, and values the same things that you do — commitment, kids, financial stability. If he’s funny, great. If he’s sexy, bonus. If he’s tall, cool.

But if you keep trying out men as if they’re a series of numbers: $100K, Masters degree, Jewish, 40, 6’, etc, you’re never gonna break your own patterns of destruction.

Love is waiting right under your nose, but I can pretty much promise you that if you’re looking for a 6’5” guy who is younger, fitter and sexier than you, you’re never gonna find it.

And if anyone here has found the 6’5” younger, sexier, richer, smarter, kinder, more emotionally available man and been with him for 5-10 years, let me know.

I’m guessing that if you have a happy 10-year relationship, you traded off on at least one of the following: age, looks, ambition, money, intelligence, emotional IQ — and you were happy with your decision.

I look forward to hearing your thoughts.

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  1. 1

    Two things:
    1. From what I remember of the little celebrity news I read, I think Brad Pitt wanted children,   Jennifer Aniston didn’t, so Brad Pitt divorced her.
    2. You might want to Google on “narcisissm epidemic” and then find a good professional to talk to about your dating/relationship issues.

  2. 2

    Is this letter real? If it is, I feel like the poster completely made it up.

  3. 3

    Funny how Ultra has gone on about a man’s desirability in terms of youth, sexiness, height, looks etc, she has not mentioned anything much about how they felt about her or how she felt about them – in an emotional sense. Men it seems, are like objects to Ultra – valued for their “functionality” and the status they bring her, not for their compatibility or companionship or the personal happiness she experiences with them. Seriously Ultra, you are not looking for love, you are looking for a glorified handbag you don’t have to share with anyone else. Treat men like one, and you in turn will be treated the same way you treat others.

  4. 4

    Mathematically, men over 6’4 – 6’5 are .1% of the population — not 1%, POINT 1. Meaning, 99.9% men are shorter than 6’5.

    So…good luck with that….  

  5. 5
    Pink Ocean


    This article resonated strongly with me. I, too, was a maximizer in pretty much all areas of my life. This included my poor choices in dating men who were not well-suited for me. I always attributed this unwise behavior of mine  to  having delayed life moments in certain  areas including   getting marriage, having children, etc. as a result of making the decision to, instead,  climb  the educational and professional ladders. Fortunately, by end of last year, I recognized that my maximizer behavior would ultimately lead me  to no where good. Shortly after I experienced this clarity, I met my amazing fiancée who is more than I could have ever hoped for in a husband: intelligent, hardworking, kind, interesting, wise with appropriate understanding, and emotionally strong. To top that off, my fiancée is also very, very good at his job, and therefore,  will be  a wonderful provider for us.

    So what is the tradeoff I made? While I no longer consider this to be a “tradeoff” given my personal growth in this department, I would say it is his  height. Previously, I only dated men who were 6 feet or taller, conventionally great looking, had graduate degrees and professional careers, etc. In the end, however, I found my 39 year old self single, disillusioned, and regretful after going through a series of relationships with this type. It was not until after I changed my attitude about not being a maximizer and becoming more of a satisficer that I found my fiancée. He is the only man I have ever known and respected  who makes me feel loved, safe, accepted despite my shortcomings, understood, and appreciated.

    Finally, to all the single women out there in their  thirties to forties (I just turned 40) who are searching for their amazing husbands, please  continue to believe  that you will find him (and I do not mean simply settling for good enough). I have found that this process  takes an investment in a great photo shoot, signing up  on an online dating site like, and giving a guy who  has all the important qualities you are looking for a fair chance in winning your heart. This worked for me, and my fiancée and I are now happily getting married this autumn.    Best wishes to you all in finding the right one.

    1. 5.1

      Pink Ocean:
      You just contradicted Evan and his article by saying “and I do not mean simply settling for good enough”…
      That’s the whole point.   Settling for good enough, not waiting and being picky for the best one!   And by the way, “settling” is not meant in a  negative  connotation.   

  6. 6

    Ultra – you say there is “no upgrade”… but yet you are dating a young player who drinks. I think there is definately an upgrade from a young player who drinks!That would be:   “a non-player  who DOESN’T drink”! –  age range your choice….  That should be possible, no?  

    Ok, so I understood what you were saying –   “there is no upgrade on 6’5 with great sex…” But why would you NEED an upgrade in those areas?? Why are you looking to upgrade on your current man’s best features?? If you must upgrade, why not upgrade on his worst features – he’s a player and he drinks. It should definately  be possible to find a partner who doesn’t do those things.

    To say what  Evan said but in a different way, I once heard an interview with a rich, beautiful famous holywood star, who was asked what she had learnt in life. She replied, “In this life you can have a lot, but you can’t have everything.” And that from someone in the  best position possible to “have everything.” But I think what she was getting at, more than anything, was not that you can’t have everything because no one is that lucky – what she meant was, you can’t have everything because some things are simply incompatible. You can’t be famous and anonymous at once. You can’t be a wife and mother  AND be free as a bird. You can’t have a boyfriend who is sexy, confident, charismatic and extrovert… but he never talks to anyone but you!  All personality traits have two sides to the coin – men who don’y drink tend not to enjoy partying. Men who are docile and easy to live with and come home early tend to do less well  in business.  Going from man to man looking for some sort of James Bond who comes home and baths the kids every night is just a waste of your own time –  give yourself a break and stop this pointless quest…
       Focus on finding a  man with  the characteristics that matter most   to you, make a list (in advance!) of the downside to those characteristics, get used to them in your mind  and vow that when you find him, you will accept the downside without a backward glance.    

  7. 7

    Could it be that Ultra is picking is picking the eye-candy guys because she’s really afraid of commitment herself? She’s going for the superficial because she isn’t ready for substance, so she sets herself up for disappointment, and then she can tell herself that the perfect man doesn’t really exist anyway?  

  8. 8

    Sayanta #2 wrote: Is this letter real? If it is, I feel like the poster completely made it up.

    I had the same thought.

    I thought Evan’s response showed some wisdom and nicely, offered advice
    that will produce happiness beyond just dating.

    A “maximiser” is just another name for a plain old ordinary perfectionist.
    A perfectionist isn’t necessarily an overachiever or an achiever at all.
    Just a person who will not be happy unless the results conform to an
    unrealistically high standard.

    My favorite saying in this regard is

    “If you will settle for nothing other than perfection that is what you will
    get, nothing”

    I thought Evan’s example from his own life with buying plane tickets
    illustrated everything very well. If you have realistic standards
    and are fine with being an ordinary human being you can save
    yourself a lot of self torture over things that are not important in the long run.


  9. 9
    Evan Marc Katz

    To my regular readers who are asking if the letter is real, the answer is yes. I’ve never had to make up a reader question in 5 years of doing this, and I don’t plan on starting any time soon.

  10. 10

    EMK – I don’t think commenters thought YOU made it up, I think they think the OP made it up…

    (EMK responds: But WHY? What would be someone’s motivation to make up a “fake” question to an advice columnist?)

  11. 11

    @Evan: I personally didn’t suspect that YOU made up the letter. I was wondering if Ultra was the kind of person who is seeking some kind of attention, by stroking her own ego… publicly.
    Anyway, assuming this letter is real, I think that her idea of upgrading is the key element. Only because she has a great sex life and the dude is tall she already sees it as the peak.
    I would suggest an upgrade: tall, good-looking, articulate, travelled the world, well-mannered, billionaire, great fashion sense, funny, kind, nice, generous, a good listener, romantic, charismatic, same ideas/goals/desires/dreams as her, no drinking, no smoking, no flirting with other women, willing to express his deepest feelings, good listener, quality sex, works-out, enjoys spending time with (her) family and friends, never argues, cooks delicious food, can perform CPR.  
    Good luck with that.

  12. 12

    @EMK #10
    People have sent fake letters to advice columnists for years.   They get something out seeing how someone will respond to a particular issue.

  13. 13

    Wow….I think most of us have had our cynical moments in dating, but this is brutal!
    As others have mentioned, I read Ultra’s letter as coming from someone who is, or has become for one reason or another, very cynical about love.    
    If I may play armchair psychologist for a moment, I would guess that something happened to Ultra, in her past, to make her afraid to date with heart in the present.   That mention of the ex-husband being a “weak cheater”, but still using adoring words to describe him…?   Maybe Ultra feels like love has failed her because she thought she had found the perfect love in her ex-husband, and he failed her.   And then she thought she’d found the ideal match in the young, hot guy who shares her music taste….and he is failing her.  
    And so, Ultra might think…why try for love?   Better to deal with statistics, “upgrades,” treat dating objectively so that when the relationship inevitably fails, at least you “got something” out of it, physically or materially.   It’s a way to convince yourself that you have some power in the situation, even if you don’t.   That you can shield yourself from hurt, even if you really can’t.
    I can relate to this, just as EMK says he can, and I think it’s a very interesting point EMK brings up about “maximizers” vs “satisficers.”   I will have to take a look at the book.   It actually strikes me as a very American concept, this concept of “maximizers.”   Especially if you show a little talent, intelligence or beauty, in this country you are told from a young age “You can do anything you set out to do!”, “You can be the best!   You ARE the best!”, “You can work your way up to the top!,” and “You can live the life you’ve always imagined….” not by improving your character and your relationship with the world, but by acquiring things, like the right shoes, the right car, and status boyfriends.
    Ultra: forget about upgrades.   Have the courage to offer a man the open-heartedness, honor and respect that you yourself deserve and haven’t been getting– AND have the wisdom to be able to offer these to the right type of man.   Step back and determine which types of guys are NOT likely to give that to you (such as rich, hot, young men for whom the world is their toy and who never have to grow up), and DON’T PURSUE THEM.   Who cares if he’s the tallest man you’ve ever met or if daddy’s a billionaire….he’s NOT BOYFRIEND MATERIAL and you are RIGHT that you deserve better, but you have the wrong idea of BETTER.  
    Think of what you’d like a man to love about you, not just now but in 30+ years from now… when body parts start to sag and material things don’t mean so much….and look for that kind of “better” in a man.

  14. 14

    Regardless if someone sent in a fake letter or not, there is ALWAYS a reason why it was posted. This letter hit a spot for me because I was battling the same thing.  
    Wait on the 50 Year Old George Clooney who only made one call a week or Love who is in front of me-the guy who calls me daily and takes me out on dates 3X a week. Of course I wanted to wait on the HOT GUY because he “seemed” better, but in REALITY, the guy who IS EXACTLY what I NEED AND WANT. He wants relationship, I put him on hold because I wanted to “outweigh” my options…………………. Yeah after waiting for NOTHING, I snapped into it before I lose the one who actually put in work, effort AND MAKES ME HAPPY.  

    Thank You Evan, I NEEDED THIS!

  15. 15

    This is so true…

    we as imperfect humans always tend to think “the grass is greener on the other side”! We are never  satisfied  always chasing after the next biggest, best, better, taller,  awesomest  (lol) things in life. Especially when it comes finding ‘the one’.  

    But unfortunately this is an illusion that many people are slaves to, for everything we need to bring happiness is already within….

    If we learn to  Appreciate  the simple things, then thats when the door to abundant happiness begins to open up.  

  16. 16

    As imperfect humans always tend to think “the grass is greener on the other side”! We are never  satisfied  always chasing after the next biggest, best, better, taller,  awesomest  (lol) things in life. Especially when it comes finding ‘the one’.  

    But unfortunately this is an illusion that many people are slaves to, for everything we need to bring happiness is already within….

    If we learn to  Appreciate  the simple things, then thats when the door to abundant happiness begins to open up.  

  17. 17

    Not for nothin Evan but my 23 yr.old furnace went out in October and the guy that came to  look at it  said the circuit board to fix it will $985.00. So I asked how much is a new one?(not knowing anything about furnace prices never having bought one) and he said $3500.00. So stupid me figures all furnaces of that size must be priced fairly even. I let them put it in and 2 weeks later I started seeing ads for furnaces for half of what I paid. Now I cry every time I see furnace sale 🙁    Obviously I wished I would of researched it at least a little and compared.

    Like you, I also bought a camera last year. A Sony Cybershot without reading the reviews. I figured a new 16 megapixel Cybershot HAD to better than my OLD 5 megapixel Cybershot. I was wrong and the reviews told me why. I returned it, did some research and went the Nikon Coolpix and I’m very happy. 🙂

    I know what you’re saying about tradeoffs and not comparing every little thing especially in the dating/relationship world. Sometimes a little comparison shopping and research(for furnace’s/camera’s)can save you a lot of discontent and money  in the future for making the wrong decision now.

    1. 17.1
      Evan Marc Katz

      I hear you, JB. I subscribe to Consumer Reports, so I don’t have to make blind decisions. But dating, by its very nature, IS comparison shopping. The problem is that too many people are looking for products that aren’t even on the market…know what I mean?

  18. 18

    I agree with Androgynous #3. I thought the letter sounded cold and sterile. She talked about superficial qualities like she was buying car. And she’s not looking for a dependable, practical, comfortable, attractive car, she’s looking for the overpriced, tricked-out, gas gussler with all the bells and whistles that will make her neighbors jealous but doesn’t suit her needs.
    Where is the passion, spirit, emotion, heart-connection in this woman?

  19. 19

    “The definition of insanity is doing the same thing over and over and
    expecting different results.”   She keeps choosing pretty players who cheat on her.

    The phrase “repetition compulsion” comes to mind.   What in her past would make her want to keep banging her head against this particular wall?

  20. 20

    Ultra,   Are you sure you want a relationship, and not just excitement and entertainment in your own personal life?   You don’t seem to have any kind of emotional reaction to the fact you seem to be cheated on repeatedly… which isn’t a bad thing.   It just seems like disinterest.
    @JB #17 – I know Evan replied, but that’s not “The Paradox of Choice” as Barry Schwarz defines it.   If you were a maximizer, you never would have ended up purchasing a camera, endlessly reading user reviews, hyper-analyzing each potential flaw and comparing it against another camera’s potential flaw… then missing the opportunity to take pictures.   It’s not ignoring all reviews anywhere.   Satisficers would choose a price-point, decide what features they want, then pick which camera meets those needs, maybe read some reviews, then make a decision.

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