Year of Love Experiment
Compress relationship learning into a bounded period of intentional dating
- Difficulty
- Advanced
- Time to result
- ~months to results
- Steps
- 5
- Confidence
- 90%
Wilson says she was far behind in dating experience and created a “year of Love experiment” in 2019. She dated about 50 people while genuinely trying to find a partner and learn through experience. The transferable mechanism is a bounded learning period: define the relationship question, create regular opportunities to meet appropriate people, observe compatibility and personal patterns, and review what becomes clearer. The number 50 is biography, not a recommended quota. People are not experiments in the sense of disposable test subjects, so honesty, consent, safety, and respect govern every interaction. The framework is useful only when repeated dating produces reflection rather than mechanical volume. Its outcome may be clearer preferences and greater experience, not necessarily finding a lasting partner within the chosen year.
Origin
Wilson says she had rarely dated and felt “behind the eightball” in relationships, so she deliberately dated about 50 people during a 2019 “year of Love experiment.” Extracted from The Diary of a CEO.
Core principles
- 01A neglected life area may require deliberate practice rather than more waiting
- 02A bounded experiment makes an intention concrete
- 03Repeated experience can reveal preferences and patterns
- 04Every date requires consent, honesty, and respect
- 05Volume is not a substitute for safety or genuine compatibility
How to run it
- 1
Define the learning goal
State whether you want to understand compatibility, reduce avoidance, practise dating, or seek a committed relationship.
Pro tip Use a goal that respects both your needs and the autonomy of the people you meet.
Watch out Do not conceal intentions to increase the number of dates.
- 2
Bound the experiment
Choose a realistic period for intentional dating and reflection without turning another person's attention into a performance target.
Pro tip Set review dates rather than a required number of people.
Watch out Wilson's figure of about 50 dates is not a prescription.
- 3
Create safe opportunities
Use appropriate introductions, apps, or social settings to meet people while protecting privacy and personal safety.
Pro tip Tell a trusted person about first meetings and use public settings.
- 4
Observe the interaction
Pay attention to chemistry, values, communication, comfort, and the patterns you bring into the date.
Pro tip Record lessons about yourself rather than scoring the other person.
Watch out Inexperience is not a reason to ignore discomfort or boundaries.
- 5
Review and adjust
Periodically identify what has become clearer and change how, where, or whether you continue dating.
Pro tip A useful outcome can be better judgment even if the year does not produce a partner.
In the wild
After years with little dating experience, Wilson used dating apps and real-life introductions during a designated year. She says she dated about 50 people, had fun with some of them, gained experience, and genuinely tried to find a long-term partner, though the experiment did not immediately produce “the one.”
→ The bounded period gave her practical relationship experience and a more active alternative to avoidance.
Common mistakes
Optimising for a body count
The mechanism is intentional experience and reflection, not maximising the number of people dated.
Treating people as test objects
A bounded personal experiment still requires honesty, care, consent, and respect for every other person involved.
Guaranteeing a partner by deadline
Wilson says she gained experience but did not find her eventual partner through a guaranteed one-year formula.
Is it for you?
Best for
It is best for an adult who wants relationship experience and can date safely, honestly, and without treating people as units in a quota.
Not ideal for
It is not ideal when dating feels unsafe or compulsive, or when a numerical target would override consent, wellbeing, or genuine connection.
From the transcript
“I had to do like a year of Love experiment”
“I dated like 50 people in the one year in 2019”
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