What ~100 People Wish They’d Known at 25 About Relationships

One of the happiest couples I met writing this blog, contentedly serving as campground hosts together in retirement. This begs the question of whether s’mores are truly the secret to a solid marriage.

Preface: In the winter of 2015, I realized I was about to hit my mid-20s with only a few incongruent career jumps and a rapidly failing relationship to show for it. The hackneyed quarter-life crisis ensued.

I started asking interesting people what they wish they had known when they were 25 years old. Then I started blogging about it. The answers, close to 100 in total, came from all walks of life: Uber Drivers to college professors to vagabonds to millionaires. Some submitted advice through the blog website, some were formal interviews, and some were be spontaneous conversations that were never chronicled.

1.5 years later as I turn 26, I’m rounding up the best wisdom that came out of these conversations. This is Part I: Relationships.


Prioritize someone who makes you feel comfortable.

Sure, it makes your heart beat faster if he’s super tall, has a rugged beard and can light a one-match campfire. But your heart is a drunk baby. Listen to your gut instead.

Andy, CEO of a successful tech startup, says,

“Well in some senses you just know, but I guess that’s not very practical. I tell my daughters — find someone who gets you. Find someone you can absolutely be yourself around.
I married my friend’s sister. She came over for a party at my house and we just talked for hours. I remember my friend coming over at the end of the night and saying they needed to leave and I just didn’t know where the time had gone.”

At the most basic level, you deserve to be with someone who respects you. That eliminates anyone who is constantly angry or cuts you down. That’s the opposite of love. If they truly loved you, they wouldn’t be able to decouple their emotions from yours. You being hurt makes them hurt. You being happy makes them happy. This applies to ‘friends’ too, as many people shared.

Chess: Too slow and boring to play with someone who doesn’t laugh at my jokes.

Beyond that basic benchmark, ask yourself if your gut feels totally settled around your significant other. It should feel like you’ve known each other your whole lives. It should feel like being together is a relief. It should feel like you can be your most vulnerable, authentic self. You’re ideally going to be with this person a long time. You don’t want to come home after a long day of work pressure and then have more pressure.

Sense of comfort also paves the way for easy communication– see below.

Own your communication.

Unfortunately, it doesn’t matter if in your head you think you are good or right. It only matters how you’re perceived when you express it and what you do to fix it.

A lot of people who think they are good at communicating actually suck at communicating. We blame our parents, we blame our past or we say “it’s just not my personality.” That’s not going to cut the mustard.

Jamie, a public school teacher from Seattle, met her husband Kevin at a personal development conference. After several failed relationships they were both relieved to be with someone else that “owns their shit.” Jaime says they’re happier than many of the couples they know because —

“Relationships are only successful if you’re both 100% accountable in them. It’s not 50/50. If something is wrong, you have too look at yourself first.”

The one common denominator in all your failed relationships is you. Communication probably played a strong role in many of them. Here are some frameworks to program into yourself for tense situations — Use them instead of emotions.

If you know you messed up:

  1. Be 100% accountable.
  2. Apologize and mean it.
  3. Make sure you understand why you messed up. Ask the right questions, show empathy for the response, and frame any solutions in the context of that response.

If you really don’t think you messed up, but someone is yelling at you:

  1. Stop the conversation. Nothing productive is about to be said. Distance yourself from this for a minute or a day.
  2. After you’re truly calm, you have a decision to make — If the reaction seems outsized to the situation:
It’s tempting to play strategy to prove your point. It will most commonly end with a flipped board and a ‘game over, buddy.’
  • (Least likely) This person is a wang. Feelings are important, but they are not the be-all-end-all. Just because someone feels something does not mean they are right or that they have a right to go off on you. If this is a trend, end the relationship.
  • (Maybe likely) You misjudged the situation and it’s a bigger deal than you thought. Even if you don’t see it the same way, you’ve still hurt someone and his or her feelings are valid. Please go back to part 1, “If you know you messed up.”
  • (Most likely) The reaction is not actually about what they are yelling about. Maybe something bad happened at work. Maybe you hit on an insecurity you didn’t know was there. Choose the extreme high road. If you own your part in what happened and put it aside, and they’ll usually be grateful and eager to do the same. Thus, once again, please go back to part 1, “If you know you messed up.”

If someone else messed up:

If this is a trend or even a single instance so upsetting that you’re going to dwell on it, it’s healthy to say something. Do so as soon as you can manage to express it calmly. It’s not fair to hold something against someone for 8 months and then explode about it.

  1. Pay attention. Figure out how you feel and why you are feeling it.
  2. Speak your truth without blame or judgment. Talk specifically about what happened in this instance and how it made you feel. Don’t make broad statements on character.
  3. Be unattached from the outcome. If you’ve followed these steps, there’s nothing else you can do.

If this doesn’t work, you may be with the wrong person. See below.

Peak happiness is the wrong goal. Strive to always make the relationship (and yourself) better.

My friend Jean-François is not French, but he is French-Canadian and that seems to count towards understanding love in a way us english speakers don’t. After a number of heartbreaks in both his professional and romantic life, he’s spent a lot of time thinking philosophically about how to approach things. He once said

“If it’s about fulfilling all my heart’s desires then the other person will never meet my expectations and that will cause disappointment and no real fulfillment. But if we see a relationship as a way of becoming less self-centered and giving… that will bring real fulfillment because you can always give more of yourself to that person.”

Life means operating as an imperfect person every day, learning and growing for the rest of your life. Marriage means you’re committing to work on an imperfect relationship every day, learning and growing with the same person, hopefully for the rest of your life. You’re going to want to find someone who presses into change rather than accepting stagnation.

If he/she doesn’t make you want to be better, doesn’t try to make themselves better, or doesn’t try and make your relationship better, it’s not going to work.

Perhaps, then, relationships are not about finding someone who tops the tower of potential mates, but finding someone who compliments your construction style and building the eternally unfinished tower together. Or perhaps I’m just really cheesy.

There’s no checkmates in love.