How to Not Die Alone

1. Understand your dating tendency: Romanticizer, Maximizer, or Hesitater

"Most of us have no idea what kind of partner will fulfill us long term."

Romanticizers believe in soul mates and expect effortless, perfect relationships. They often miss out on great matches by waiting for a fairy-tale romance. Maximizers obsessively seek the best possible option, struggling to commit due to fear of missing out. They may end promising relationships prematurely. Hesitaters delay dating, believing they need to improve themselves first. They miss opportunities to develop relationship skills and find compatible partners.

Understanding your tendency helps you recognize and overcome your dating blind spots:

• Romanticizers: Focus on realistic expectations and give potential partners a fair chance
• Maximizers: Learn to be satisfied with "good enough" and commit to exploring relationships
• Hesitaters: Start dating now, imperfections and all, to gain experience and find compatibility

2. Focus on qualities that matter for long-term relationships

"Great relationships are built, not discovered."

Prioritize character over superficial traits. While qualities like physical attractiveness and shared hobbies may seem important initially, they matter less for long-term happiness. Instead, focus on:

• Emotional stability and kindness
• Loyalty and reliability
• Growth mindset and ability to handle challenges
• Communication skills and willingness to address issues
• Shared values and life goals

These qualities contribute to a strong foundation for lasting partnerships. Look for someone who brings out the best in you and with whom you can grow together over time.

3. Overcome the pitfalls of online dating by expanding your filters

"We think we know what we want when it comes to a partner, but our intuition about what will lead to long-term happiness is often wrong."

Dating apps can reinforce unrealistic expectations and lead us to focus on superficial qualities. To use them more effectively:

• Expand your filters: Be open to potential matches outside your usual "type"
• Look beyond profile basics: Pay attention to how someone communicates and presents themselves
• Limit your options: Avoid overwhelm by focusing on a few quality matches at a time
• Move to real-life meetings quickly: Prolonged online interactions can create false expectations

Remember that compatibility often develops over time, so give people a chance beyond their initial profile impression.

4. Meet potential partners in real life through strategic event attendance

"You can't figure out what you like (and what you don't) if you don't date different people."

Use the Event Decision Matrix to choose activities likely to lead to meaningful interactions:

1. Plot events on two axes:
   • Likelihood of interaction with others
   • Likelihood of personal enjoyment
2. Prioritize events in the upper-right quadrant (high interaction, high enjoyment)
3. Commit to attending at least one such event per month

Additionally:

• Ask friends to set you up
• Reconnect with existing acquaintances
• Practice striking up conversations in everyday situations

Diversifying your approach increases your chances of meeting compatible partners.

5. Design better dates by shifting from evaluative to experimental mindset

"The point of the first date isn't to decide if you want to marry someone or not. It's to see if you're curious about the person, if there's something about them that makes you feel like you would enjoy spending more time together."

Move away from "job interview" style dates that focus on evaluating the other person. Instead:

• Choose creative activities that encourage interaction and playfulness
• Practice active listening and support responses
• Limit phone use and be present in the moment
• End on a high note to take advantage of the peak-end rule

After the date, reflect on how you felt using the "Post-Date Eight" questions to assess compatibility beyond superficial criteria.

6. Reject the myth of instant chemistry and embrace the slow burn

"The spark isn't a bad thing in and of itself. It can be a useful signal that you're attracted to someone. Plenty of good relationships start with the spark, but plenty of bad ones do, too."

Don't rely solely on initial "sparks" or intense attraction. These feelings can be misleading and often fade over time. Instead:

• Give potential partners a fair chance, even if there's no immediate chemistry
• Recognize that attraction and connection can grow with time and shared experiences
• Focus on developing a strong friendship and emotional intimacy alongside physical attraction
• Be open to discovering unexpected qualities in people as you get to know them better

Remember that many lasting relationships start as slow burns rather than instant fireworks.

7. Navigate relationship milestones with conscious decision-making

"Psychologists describe two ways couples transition into the next stage of a relationship: deciding or sliding. Deciding means making intentional choices about relationship transitions, like becoming exclusive or having children. Sliding entails slipping into the next stage without giving it much thought."

Make conscious choices at key relationship stages to ensure alignment and commitment:

• Define the relationship (DTR): Have explicit conversations about exclusivity and expectations
• Moving in together: Discuss long-term goals and what cohabitation means for your future
• Getting engaged: Address crucial topics like finances, family planning, and shared values

Use tools like the Critical Conversation Planning Doc to prepare for these important discussions and avoid misunderstandings.

8. Break up compassionately when necessary, using a structured approach

"You're underestimating her opportunity cost of being with you. The longer you put off breaking up with her, the less time she has to find a new partner and build a family."

When a relationship isn't working, follow these steps for a compassionate breakup:

1. Record your reasons for wanting to end the relationship
2. Set a specific deadline for the conversation
3. Plan what you'll say and how you'll address potential reactions
4. Create an accountability system with a friend
5. Have the conversation in person, being kind but firm
6. Avoid post-breakup sex and create a plan for the immediate aftermath
7. Use a Breakup Contract to establish clear boundaries moving forward

Remember that breaking up, while painful, can be an act of kindness when done thoughtfully and with respect for both parties.

9. Reframe heartbreak as an opportunity for growth and self-discovery

"Whether you believe the date will go well or poorly, you are right. You're self-sabotaging if your pre-date mantra sounds something like: 'Obviously, this isn't going to work. It hasn't worked the last hundred dates.'"

Use cognitive reframing techniques to process the end of a relationship more positively:

• Focus on the positives of the breakup (newfound freedom, personal growth opportunities)
• Acknowledge the negatives of the relationship to gain perspective
• Rediscover yourself through activities and interests you may have neglected
• Learn from the experience to make better choices in future relationships

Engage in self-reflection exercises and consider professional support if needed to navigate the healing process.

10. Decide on marriage thoughtfully by addressing crucial topics

"Even if you wait a few years, love can still obscure your priorities. When I interviewed a series of divorce lawyers (a bit of an awkward hobby to explain to Scott), several said that couples often make the same big mistake when considering marriage. They're so fond of each other that they assume the other person wants the same things in life; therefore, they don't set aside the time to talk explicitly about major decisions like where to live or if they want children."

Before getting married, have in-depth conversations about:

• Family planning and parenting styles
• Financial goals and management
• Career aspirations and work-life balance
• Religious and spiritual beliefs
• Expectations for extended family involvement
• Conflict resolution styles and communication preferences

Use tools like the "It's About Time: Past, Present, and Future" exercise to explore these topics thoroughly and ensure alignment on important life decisions.

11. Build lasting relationships through intentional love and regular check-ins

"Creating a relationship that can evolve is the key to making it last."

Practice Intentional Love to maintain a strong, adaptive partnership:

• Create a Relationship Contract: Outline shared values, goals, and expectations
• Implement weekly Check-In Rituals: Discuss ongoing needs, concerns, and appreciations
• Regularly reassess and update your agreements as you both grow and change

Remember that great relationships require ongoing effort and communication. By consistently investing in your partnership and adapting to life's changes together, you can build a resilient and fulfilling long-term relationship.

Last updated: January 22, 2025