dear bear: the secretary problem

George Bellows, New York, 1911

Hi Bear,

I’m in a happy relationship with my girlfriend of five years yet engagement scares me. We have a great relationship and few problems, yet I can’t help but wonder/realize that there are infinite other relationships I could be having. Some of them which would be equally good/better. How do you deal with the secretary problem as someone who is an optimizer? I know the famous advice blog post ‘the truth that lives here’ with the advice ‘just leave’ but that doesn’t feel right either—we have something great. Part of me thinks the issue is that I should commit more, the other part is scared to commit more and make an irreversible mistake.

Dear Bear,

Effort is most useful when correctly directed. I think everyone knows people who underoptimize (people who are really great and desirable who end up in bizarrely bad situations), as well as people who overoptimize (awesome, lovable people who are like, yeah, I went on 200 dates this year and I didn’t like a single person).

You, Bear, want to be someone who doesn’t overoptimize or underoptimize. You want to be someone who can appreciate a good thing for what it is, yet can recognize when you’re unfulfilled. You want to try really hard, but you want your effort to be fruitful. In an age where we’re drowning in optionality, you want to have an awareness of what is available to you, but ultimately stick close to your values. Here are some questions I suggest you ask yourself:

• What are your values? What matters to you in a partner? I’m not asking what you think you want, I’m asking what bothers you in daily life, as well as what brings you joy. I think a lot of people take a very cerebral, egotistical stance on this—is my partner the fantastical person of my dreams? Ditch that, and try to notice your actual experience. What kind of person do you find yourself drawn to again and again? Is there cognitive dissonance between what you claim to want and what you seek out? When have you felt the purest joy?

• Is what you feel fear, or dread? Are you afraid of your relationship because it forces you to be inconveniently accountable to life, or because it makes you feel dead?

• Do you feel really, deeply understood by your partner? (This is really important!)

• Are you compelled by the idea of infinite choice (bad) or by the idea of different tradeoffs (potentially good)?

I’m thinking about a long car ride I had once with a guy who told me the story of his relationship with his partner. They dated for four years, and then he broke it off because he wanted to date someone who was more intellectually challenging. He thought that someone who was more of a sparring partner, more similar to him, would make him happier. He found someone like that, and discovered in the next couple years that he was terribly wrong—he did not in fact value the quality he thought he did. He repented. He is now married to the person he once broke up with.

Now let me tell you about another friend. She happily dated her partner for four years, and then broke it off because she wanted someone who was more adventurous—someone who was up for a more intense life vs a cozier, slower one. Someone who would understand her references instead of turning away from them. It took a couple years, but now she’s dating someone who lives life at a faster clip. She’s certain that she made the right choice.

Someone else’s story is never going to be yours. If you look for stories that confirm you’re right for staying, you’re going to find a thousand. If you look for stories that confirm you’re right for leaving, you’re going to find a thousand. No amount of research is going to protect you from being wrong. At the end of the day, you have to shimmy into the locked box of your heart and make a decision about what you really value. What you value is probably not what you want to value. You may be more timid than you think you are. You may be more bold than you’d like to be. What lies at the bottom of it all, when all your excuses fall away? I can’t tell you whether your doubt is the truth of it or your faith. You have to stay with yourself long enough to see.

I’ve always been the perpetual student—a studier, a researcher. I’ve always believed that would save me. I’ve read the Cheryl Strayed letter you’re referencing a thousand times. I’ve read every Ask Polly column. I’ve prayed for answers in the form of dice rolls, birds landing on particular roof shingles, advice from particular friends, books flipped to random page, and I really believe that at moments I have received signs from God. And all the same I’m telling you at the end of the day no sign will save you from the weight of your own decisions. You have to make a choice. And you should remember that you’re always going to be incentivized to lie to yourself to make it easier.

I do think that if you have friends who know you really well, whom you trust to be honest with you, you should ask them what they think. They’ll tell you what you’re blind to.

Remember: infinite amounts of the wrong thing will never make you feel full. But the right thing weighs you down in the best possible way.

Good luck,
Bear

If you have questions for Dear Bear, you can ask them here. :)