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. 31

     If the woman who wrote the letter really thought about it, she could probably come up with a list of at least 200 ways the last 3 guys she dated did NOT measure up, and find someone who is a better quality match. She shouldn’t put these losers on a pedestal, especially considering their unevolved player-type personalities. She should find herself a nice, but ordinary, vacuum cleaner salesman type of guy from Minnesota. They have a lots of tall, Norwegian-type guys who aren’t completely stuck on themselves. She needs to focus on character, and less on the superficial flashiness of the men she is dating. 
    Another good book is “Decoding Love,” by Andrew Trees, although some of his observations are not very insightful, he does use real scientific research, which is great food for thought.

  2. 32

    I think the short answer is yes. Ultra, you should keep trying to find a better boyfriend.  

  3. 33

    I think good points that are probably indicative of the truth are made by both @Sharon 27 and @Ruby 28 / 7.

    Ultra, I had a (male) friend who was cheated on by his now-ex wife, and had done a lot of reading about cheating w/in marriage.  He says that it can make you feel revulsion against yourself, and I can echo the sentiments by the previous posters that maybe there is a sense that if you ran into your ex-husband, perhaps you would like to show him that you can do a million times better than him, in only measures that could be determined by a one-minute crossing of paths on the street?

    Have you had therapy, or done work on yourself to emotionally process and deal with your ex-husband’s affair? 

  4. 34

    ** and, in addition to my post #34, would lead to her comparing herself to Jennifer Aniston, a former wife who had the “best” man, then was cheated on by him and has been romantically floundering for 6 years or so.

    Ultra, like many women,  I think you probably should work on yourself and get over the affair and stop comparing new boyfriends to your ex-husband, and trying to outdo him.

  5. 35
    Saint Stephen

    So humans have turned into software that women like our OP just wants to keep on upgrading and upgrading. And when did tall become better? I never knew men’s quality were defined by their height. That means Mark Zuckerberg must be of a very low quality in the hierarchy of potential boyfriends. Maybe his fiancee didn’t get the memo that taller guys are better quality. Oh wait… she must have been into him because of his money.

  6. 36

    This letter reads like it was made up by one of those “manosphere” bloggers.  In a few days time, one of them will link to this article and use it as “proof” that women are unreasonably hypergamous, then wait for misogynistic comments to roll in.

    Anyway EMK, I thought your answer was extraordinarily compassionate, considering how outrageously high the OP’s standards are, and there was a lot of good advice for anyone whose standards are pricing themselves out of the dating market.

    Personally, if I can find a healthy, financially secure man with whom I shared a mutual attraction, respect, family values and fun, I’d feel like I’d won the lottery.

  7. 37

    @Angie #21 I see your point about the camera and like others have said I may not be a “maximizer” when it comes to household things. But yes, I had to have a furnace and even though some may not agree I have to have a camera for my profession.

    No one HAS to have a relationship(SO/spouse). I’m definitely a maximizer in my personal life. I’m not proud of it. It is what it is. I’d love to have a wonderful woman in my life but when I don’t life still goes on and I keep looking. Being that have no desire to be married there’s no pressure or time limit on finding someone.

  8. 38
    Christie Hartman

    “I chose to focus on one thing: how I felt when I was around her.”
    That is Evan’s quote, and it is the best and most important one in this particular article. That hits it on the head. The minute you start looking for partners in terms of their height, income, hotness, you decrease your chances of ever finding that great connection, that great love, that great partner. This is why online dating is such a frustration for so many – it encourage people to shop for attributes. The thing is, when you do find that great connection, as long as the attraction is there, you won’t CARE about those other things.
    Saint Stephen (36): LOL

  9. 39
    Joyful Girl

    Thank you for the book review! I am around a lot of people who seem to not recognize they actually have choices, because they feel victimized by their circumstances (state of health, upbringing, current marriage, etc.). The other side of that pendulum swing, however, is exactly what you referenced: the paralyzation and self-destruction that occurs when there are too many choices. Anything that helps people (me, included) find that balance between no choices and too many choices would be a great reference to have around!

  10. 40

    I just finished reading the book and a couple of things he said resonated with me:

    “The existence of multiple alternatives makes it easy to imagine alternatives that don’t exist…alternatives that combine ALL the attractive features of the ones that do exist”

    Into one delusional expectation of looking for someone that has it “ALL” or no one else will do. Leading a lot of people in online dating to be miserable.

    In another part of the book he says something I disagree with he says

    Social relations are different we don’t dismiss lovers the way we dismiss restaurants, cereals, or vacation spots. Treating people this way is unseemly at best and reprehensible at worst.”

    The way people treat each other in the online dating arena is everyone is “disposable” because (and especially for attractive women) they have so many options and choices that the outcome with any one person is irrelevant. Before the internet it wasn’t this way because no one had that many options at their fingertips. I do it myself occasionally without even thinking twice ie: “she’s cute but she has twin 7 yr.olds” and travels for work…next  “She’s has a pretty face but she’s too tall and lives too far”……next She’s exactly what I’m looking for but low and behold she’s NOT attracted to ME”………… It never ends 🙁

  11. 41

    Hey I’d be happy just to have the cast offs!

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