The Pragmatist’s Guide to Dating

In my previous post, I explained how the key to a lasting relationship is selecting your life partner in the same manner in which you would choose a business partner (you should read it if you haven’t already). Well, here’s my follow-up to that post.  I’m sharing some of my favorite tips—things I’ve discussed with only my closest friends. You’re welcome.

Selecting the Right Candidate

Business woman sitting at interview in office

You want the best of the best, but keep in mind that “best” does not mean “perfect.” Create a list of substantive deal-breakers and stick to it. By deal-breakers, I mean things that you will not accept in a partner.  Drug use, smoking, psychosis—these are some of the more common red flags that signal “DO NOT PASS GO.” Just remember that the longer your list, the harder it will be for you to find someone. Maybe some of those deal-breakers can be shifted to the “I wouldn’t be crazy about this but I can live with it” list.

The Probationary Period

Portrait of a businessman praying with crossed fingers

This is the first 12 months of your relationship. Twelve months may seem like a long time, but it was the same amount of time that I was on probation when I was an Assistant Conductor for the Long Island Rail Road back in the day. They were pretty strict, but with good reason—as you should be in a new relationship. Remember, people show you their best version of themselves in the beginning. Crazy is hard to keep hidden for a year. If you detect a hint of crazy during probation, nip that ish in the bud and keep it moving!

Relationship Start-Up Capital

Sad girl

This refers to the amount of time, effort and yes, money, that both parties are willing to invest to get the relationship off the ground. During the probationary period (and beyond), be sure to analyze the amount of capital that you’ve invested and compare it to that of your partner’s. Are things one-sided? Are you always the one calling? Is one person doing all the spending while the other’s doing all the taking? If that’s the case, then what you have is a sole proprietorship. In a true partnership, it takes two to make things work.

Now, keep in mind that this is by no means a complete list. And, of course, there are exceptions to every rule—except these three. Good luck!

Until next time,

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