Understanding the Optimal Stopping Problem
The optimal stopping problem—also known as the secretary problem or the 37 percent rule—addresses a fundamental challenge: how to select the best option from a sequence of candidates when you cannot revisit earlier choices. In dating, this translates to a concrete dilemma: if you meet ten potential partners over your lifetime, which one should you choose?
The mathematics reveals a counterintuitive answer. You should not immediately select the first attractive person you meet. Instead, you should date a set number of people purely to understand the dating pool, then commit to the next person who surpasses everyone you've encountered so far. Research by experimental psychologists including J. Neil Bearden and Amnon Rapoport has shown that people naturally reject this strategy and settle too quickly, missing objectively better matches later on.
Calculating Your Dating Sample Size
The core formula determines how many potential partners you should evaluate before applying your selection rule. This depends on your dating frequency and the timeframe you're willing to invest.
Total candidates = Dating frequency × Time period
Dating frequency— Number of dates per unit time (e.g., dates per year)Time period— Length of your dating window in the same unitsTotal candidates— Total number of potential partners you'll encounter
The 37 Percent Rule and Success Rates
Once you know your total dating pool, multiply by 0.37 to find your evaluation threshold. If you'll date 100 people, evaluate the first 37 and then commit to the next person who exceeds that entire group. This strategy maximizes your probability of selecting the best partner from your available pool.
However, success isn't guaranteed. The optimal stopping strategy has inherent risks. If your ideal partner appears within your evaluation phase, you'll necessarily reject them according to the rule. You then continue meeting people, but nobody matches that earlier standard. You may end up having to reject everyone else and finish alone. The trade-off is that this algorithm gives you the best mathematical odds of securing an excellent partner—roughly 37 percent success rate—compared to random selection or other intuitive approaches.
Real-World Adjustments and Rejection Probability
The pure optimal stopping model assumes you'll succeed with anyone you choose. Reality is messier. Your prospective partner might reject you, or mutual attraction might not develop. This calculator incorporates a rejection probability to reflect that becoming a couple requires agreement from both parties.
Additionally, you don't necessarily need to find the absolute best match. If you'd be satisfied with your top 5 or top 10 candidate instead of settling for nothing, your success rate improves significantly. Specifying this threshold in the calculator adjusts both the rejection percentage and your probability of ending with a partner. These real-world variations make the tool more applicable to actual dating decisions rather than abstract mathematics.
Common Pitfalls in Dating Strategy
Applying optimal stopping theory to your love life requires honest self-assessment and realistic expectations.
- Underestimating your dating pool — Many people either vastly underestimate how many potential partners they'll meet or overestimate how long they're willing to date. Be conservative with your time horizon and dating frequency estimates. A miscalculation here throws off your entire evaluation threshold and can lead to either rejecting too many people or committing too early.
- Confusing 'better than all previous' with 'perfect' — The strategy doesn't guarantee you'll find your soulmate. It identifies the first person who beats your sample group, not someone objectively perfect. You might pass on someone decent during evaluation phase expecting to find someone extraordinary later, then face disappointment.
- Ignoring mutual selection — The model assumes if you choose someone, they'll choose you back. Real dating requires reciprocal interest and effort. A high rejection probability significantly lowers your success rate, so factor in honestly whether your target matches would likely accept a relationship with you.
- Forgetting this is probabilistic — Even with optimal strategy, you have roughly 37 percent odds of success. That's better than random choice, but it's still a coin flip with worse odds. Don't interpret the calculator's recommendation as a guarantee or become frustrated if the outcome doesn't match the theory.