Every failed relationship (or attempt at a relationship) has plenty to teach you – in terms of things you got right, or wrong. Things that would make you cringe later on, and others that would make you wonder why the relationship failed. Each failed relationship (or attempt) helps you recalibrate yourself as a person – in terms of what kind of people to go after, and what kind of strategies to adopt during the process. Thus, a relationship is important not only from the direct joy it provides you, but also in terms of learnings for future relationships.
The standard model about “finding your level” in terms of determining your expectations from a potential partners involves trial and error. You “sample” by hitting on someone who you think might be a good fit. If it goes well, story ends. Else, you “learn” from this experience and hit on someone else.
How good a learner you are determines how many attempts you’ll take to find someone “your level” who is a “good fit” and end up in a great relationship. Yet, the kind of attempts you make puts a natural cap on the amount of information you extract from the attempt.
For example, there might be a potential counterparty with whom you have an extremely low (close to nothing) chance of getting into a relationship. Conventional wisdom says that you shouldn’t attempt hitting on her (to avoid pronoun confusion, let’s assuming that everyone you can hit on is feminine. Adjust accordingly if your preferences vary), for the odds are stacked against.
While this is good enough reason not to attempt that relationship (though sometimes the downside might be low enough for you to take a punt), the other problem is that you don’t learn anything from it. The extremely low prior probability of succeeding would mean that there is no information from this that can help tune your system. So you’re wasting your time in more than one way.
It works the other way also. Let’s say there’s someone who really looks up to you and wants to be in a relationship with you. You know that all it takes for you to get into a relationship with her is to express interest. If you know the relationship will add value to you, go ahead. However, it is absolutely useless in terms of your “find your level” – the extremely high prior probability means it won’t add sufficient value to the process.
So while they say that someone who’s been through failed relationships (or attempts at relationships) is experienced and has a more refined set of expectations, the sheer number matters less than the quality. It is the amount of information you’ve been able to extract from each such relationship (or attempt). A one-sided (where one of you is clearly “out of the league” of the other, doesn’t matter who is who) relationship doesn’t add much value.
Happy Valentine’s Day!