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

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.