The Best of This Modern Relationship Guide: Make It Happen

The title in question: Logan Ury’s “How Not to Die Alone.”

Hitting like a freight train chock full of superb advice, Logan brings their years of learning (Harvard), behavior science (Google), industry know-how (coach and director at dating-app Hinge), and personal relationship-building (and deconstructing) experience without hesitancy. The book is a firehose of info backed with findings from the likes of psychotherapist Esther Perel and the renowned Gottman Institute.

Having read it multiple times, I finally come up for air. Now I want to share with you part 1 of the best I’ve gleamed from this modern relationship guide.

  1. You Date 3 Ways
  2. 3 Ways to Attach
  3. Partners Are Better Than Prom Dates
  4. Who Are Your OSOs?
  5. To Date a Stranger IRL
  6. Ask Friends!
  7. Ask Friends IRL ~
  8. For Every Date IRL
  9. How to Keep a Relationship Alive?

You Date 3 Ways

3 tendencies make up how people seek out others in their life:

  • The Romancer – Thinking there is “The One” and only “The One” and “The One” will fall into your lap (sometimes literally in the person’s imagination). The “Disney Romance” fantasy. Preconceived notions of who and how relationships will go, leading to passivity and unfounded bias in life.
    • Growth: Be aggressive and proactive in finding your “One.” Loosen up the dating criteria. Come to terms that “happily ever after” is a lie – the prince/princess will have blemishes, perhaps catastrophic bumps in the road, and ultimately you both are only human.
  • The Maximizer – Knows the optimal, seeking perfection exclusively. The crusade ultimately makes the mathematically perfect (yet imaginary) partner the enemy of the great and real. Things could always be better, so when they are not, quick to ditch or seek to change others.
    • Growth: Become a Sufficer. I (a Maximizer) use this self-created advice in my life which has helped others end and start relationships: “Don’t settle but suffice.” Also helpful:
      • The Secretary Problem: Not the actual name of the mathematical optimal proof, but used in the book. A tool to determine if the “sufficient” and “optimized” choice has been made when you don’t know what options are available and a denial-to-commit cannot be undone. Grants great safety against doubts of “did I settle?”

        Figure out the sample size for dating (say, start dating at age 20, hope to be settled down by 40; 20 years). Figure out what 37% is of that (20 years = 7.4).

        Date as many people and as much as possible in the first 37% of the sample (ages 20~27), making sure not to permanently commit (e.g. marriage, children, houses, face tattoos, etc.) to anyone during that time.

        Explore, discover, and improve. When 37% is past, determine who the best person was who was dated in that time (subjective criteria of positive feels, partnership, similar goals and values, etc.).

        Then keep dating (ages 28~40) – once you find someone who is as quality or greater than the one met in the first 37%, commit and put in the work to make it work.
  • The Hesitater – “I’ll be ready when …” Based in fear, responsibility for action is sidelined in favor of side projects and goalpost moving, meaning relationships do not happen for (ultimately) meager excuses.
    • Growth: START DATING! Make friends! Get out! Now! Begin getting the numbers and experiences in, the reps and xp. Set deadlines and leverage 3rd party accountability (e.g. a friend expects a 15 minute progress report every week, etc.).

3 Ways to Attach

It is understood folks have styles of attachment to other people that come in 3 flavors (though a super-minority fourth – the Fearful – exists that needs a lot more care than a book or blog post can provide):

  • Secure – Confident and competent on their own or with others. Can set boundaries and communicate clearly. Seems nice and put together, but at the chance of seeming boring. About ~50% of the population yet scarce in the dating pool – is readily capable of making relationships (even with other styles) work, so are likely already committed.
  • Avoidant – Pulls back when things get too close. Needs independent space (even if only occasionally) and often takes it without communicating what they are doing. May pretend aloofness.
  • Anxious – Draws close. At times over-communicative, desiring feedback. Seeks care and intimacy at cost. Classically “needy.”

Secure style can bond with any other style and make it work. Avoidant and Anxious folks, however, especially since they are the majority of the dating pool, try to bond (Avoidant+Anxious) only to fall into a cycle of getting close then rubber-banding apart (Avoidant tries to meet Anxious close-space needs, eventually taking space away only to be pursued/chased by the Anxious – a vicious loop).

Attachment styles can change over time (the book says after about 4 years of personal growth or trauma). In my own experience, any style can be learned (though only Secure is worth striving to become), yet acting in it day in and out, the good times and the bad, will be many years of work – e.g. a learned-Secure person may regress to their Anxious or Avoidant tendencies given enough stress.

As another tidbit, I have seen attachment styles in other mammals too. Fascinating stuff.

Partners Are Better Than Prom Dates

“Partners” are the long-term folks who are stable, loyal, caring, and kind. Ride-or-dies through the highs and the lows. Have their s*** together with long-term (6-8 year) timelines minimum.

“Prom Dates” are the short-term folks who optimize for fun now-vs-later, good-vibes-only, go-with-the-flow, and impulsive. Enablers. Live in fantasy, thinking of at most the next few months if not just the next few days. Spicy.

Partners can be observed by their emotional stability, unconditional kindness (think, no uncalled for suffering), dedication (e.g. keeping healthy long-term relationships of any kind), growth, knows how to and does fight well, and repairs damages. They express affection, appreciation, apprehensions, and apologies right away without hesitation.

Prom Dates share important interests or hobbies and will introduce novel and “fun” things to do. They can be identified by great times out, perhaps some intense memories. Ready to go and high-burning.

While many folks say they want a long-term Partner, they almost always in the beginning look for the traits of the Prom Date: Does a potential interest share the same interests in music / movies / food? Have they been to as many countries as I have? What is their job and income? Do they cook or clean or own a home? Not watch daytime TV? Are X height and Y weight?

These are aesthetic wants and pet peeves, not what a long term relationship needs. Again: Kindness, caring, long-term timelines, emotionally stable, dedicated, growing, fights well, repairs, generally has s*** together.

While having things to do together can be important, it is not the end-all be-all of a long-term relationship. Tastes change, bodies age, priorities shift, time is finite.

Rather, focus on where more time is spent in relationships: Domestic tasks, minimal wealth thresholds (can they support themselves independently), quality of friends, respect for you and your own activities. Anything occasional could be classified as a want or a self-care/-soothing responsibility.

Tldr; Save the needs, kill the pet peeves. Fix your filters to find yourself a long-term Partner vs. the Prom Dates you have been getting.

Who Are Your OSOs?

No person should have all their wants and needs fulfilled only by a single person – that is a tragedy. Logan suggests an alternative: Other Significant Others (OSOs).

An OSO is a person important things can be shared with. Want to go rock climbing but the Partner has bad knees? Call up the OSO gym buddy. A lifelong gardener but the Partner has really bad allergies? Volunteer or start a community garden. Want to do something but the Partner doesn’t care for it? For incidentals and hobbies, it is OK to seek like-minded friends outside the 1:1 relationship.

To Date a Stranger IRL

This is going to sound a lot like the “Flirtology” post. Go there for more depth on how to meet in-real-life ~

Final chime in here: I remind you that dating is serious business. It ought be treated like a job if you aim and choose to have someone in your life for whatever reason. Be proactive, be consistent, be knowledgeable enough to know what your wants and needs are and capable enough to express them. Put in the time to grow yourself and beat the dating odds since they are in no-one’s favor.

Get off hit-and-miss apps that are designed to keep you guessing and get out IRL.

Go to public events alone (or with a great wing person not looking to hook up themselves) where you 1) enjoy the activity for its own sake, and 2) will be forced to interact with other people. Everything else is a skip in terms of where to spend your seek-a-date time.

Approach who you are interested in: Introduction (“I” statement), comment (about a context or the other person), ask (open-ended opinion question). Or, focus on props, be playful, ensure a follow-up post convo if the feels are there.

Not sure the other is interested? While you ought be gradual in finding this out, you can be upfront in asking “Are you in Love?” (Pauses here might mean they are in open dating or tentatively exclusive, yet have doubts on commitment with who they are with.) Something more casual: “I liked our conversation here and I want to talk it over with you more – how can we follow up after this?”

Still stuck on where to meet people? Get into a line 🙂

Ask Friends!

Simple: Ask your friends to set you up on dates with their friends. What have they done for you recently anyway?

Keep in mind: You must follow up on the date – respond to texts promptly, arrive on time and clean if you get to in-person. Do not let your friend (and theirs) down. Deliver feedback gently through your mutual friend.

Having trouble getting friends to cough up connections? Offer up a bounty – say, a reward for an IRL date (of course, get texting introductions out of the way first), another for 6 dates with the same person, etc. Incentives matter 💯

Ask Friends IRL ~

Maybe the answer to meeting people lies with those you have already met. Sometimes we cannot see the quality trees next to us for the vastness of the forest of possibilities.

After you read this paragraph, stop for a moment to think: Who do you know nearby that you enjoy spending time with? Trust? Can admit is attractive in mind and body to you? Is or may be open to new romantic relationships?

Thought about it? You now may have someone(s) in mind you have already built a relationship with that could be built out in other ways. It could be time to go on a friend-date and have a decidedly fateful conversation.

BEWARE: You have a level of trust with whoever your friend is. You may have shared social groups and routines that will be put at risk in escalating things. So mitigate:

You must act delicately in response to your thoughts and feelings. They are your responsibility, not your friend’s. Should the friend give indirect answers, a change of subject, or outright rejection, you must move on and avoid bringing it up again. Do not make this weird, do not betray your friend this way.

That said, you will only know if you ask something in person something such as:

Have you ever considered us as more?

So what if they say “yes?” Fantastic! Now you can get down to business in defining the relationship (more on this in another section). Something else to add should you have overlapping activities or social groups: How can the romance gracefully end if either party chooses to discontinue to preserve the joys you can still have as platonic friends and with your groups?

Anyway, a quip I often recall: Life is better with friends.

For Every Date IRL

Skipping here the online dating suggestions. Most of it is what you have likely heard before – good photos, thorough bios, initiating, meeting fast, etc. Read the book for more!

For first or thirty-first dates, a few bits of unordered mindful advice:

  1. Go on a “3rd object” (as Jean Smith puts it, a “prop”) date.
  2. See your date interact with others – service folks, randoms on the street, your friends, their friends, attractive people of all sexes and genders and races, etc.
  3. Work together at some point on the date. Collaboration is bond building. Play is a great choice!
  4. Silliness and messiness on a date can be great – it opens up conversation, shows a vulnerable side, and defuses what could otherwise be a tense meetup. While you ought be the initiator on this, go slowly to not go overboard.
  5. Dim the lights. Queue the gentle/upbeat/happy music.
  6. Show the effort being put in. Share the thought you put into choosing the place, making accommodations for the other, work done to make things happen. Effort from the person equates to value in the person.
  7. Go deep. As James Sexton put it, “get to heartbreak faster,” most easily done by acting and asking and telling like you and your date are in the middle of a romantic relationship already. Authenticity is too rare, fantasy kept alive too long.
  8. Listen. LISTEN. Listen to understand.
  9. Make sure you are telling/revealing about yourself, but be comfortable with silence and know when to ask after the other person (i.e. when to shut up when not answering a Q thoroughly yet concisely).
  10. No phones. Not in hand, not on the table, not making sound (vibration can be OK if using discretion). Ignore all texts and non-emergency calls.
  11. End on a high note (a laugh is great for this). Having a semi-flexible deadline to leave (e.g. bedtime, an alarm for 3 hours in, etc.) is a great cue and excuse for looking for that high-point departure.
  12. My additional advice based on psychology: wear red. Red is attractive, winning, and a first among otherwise equal choices.

After the date, Logan suggests taking “The Post-Date Eight” feels review (here @loganury).

How to Keep a Relationship Alive?

Addressing chemistry (i.e. “the spark”), having “the talk,” navigating trouble, recovering from breakups, super-serious committing, and bonding – read now how to do this and more in the last-half of this review.

Now you (hopefully) have a date. To take the relationship to the next step and beyond, I needed to split up >5000 words into two parts (second part here).

I have been constantly recommending “How Not to Die Alone” since it landed on my library loan shelf. I recommend it to you – while I tried to be comprehensive, there is no way, no way to communicate the same impact and influence Logan brings to the page (or audiobook, in my case).

So get started. Go figure yourself out – where you have been, where you are, where you are going, where you want to be. You have the tools, you have the ability, you can make the time.

I am still glad you are here and I want to see you back next week for the final part. Cheers to your personal growth and relationship progress in the meanwhile ~ ❤

Published by

Jimmy Chattin

Processor of data, applier of patterns, maker of games and stories.

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