Some Random Dating Guidelines

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Love Jones (1997), starring Larenz Tate and Nia Long

As a decent-looking 40-ish man living in New York City with a halfway decent job, I’ve had lots of experiences with dating. Younger women, older women, divorced with kids, working class, professionals, professors, etc. New York is the land of perpetually-single people. At the same time, however, having been married and divorced with kids early on, I had to learn to be extremely efficient in my dating activities, as my weekends were spent mostly in New Jersey with my kids. And what is dating, after all, but a giant game of elimination?

I recently got (re-)married, so now that my dating experiences are in the rear-view mirror, I can reflect on them with the pseudo-wisdom of a Grammy-winning rapper reflecting on his past hustling days. So without further ado, I’m presenting some (but by no means all) of the lessons learned from my dating experiences. In no particular order:

  1. Here’s a simple, but important, formula: If a trip is scheduled x amount of months into the future, and you’ve been dating someone for less than x months, do not invite them or plan to bring them on that trip! For instance, if you and your friends have a previously-scheduled trip in four months time, and your significant other of three months asks if they can join, the answer is always no, even if (and, I would argue, especially if) your friends are bringing their significant others. (It’s still awkward.)
  2. Never date an ardent conservative who’s on public assistance or benefits from government largesse in any material form. Trust me, get out while you can! You don’t want that kind of hypocrisy in your life.
  3. In the same vein, never date an ardent liberal who does not have any friends who are underrepresented minorities. Really?! You live in New York City, but don’t have one black or latino friend? (No, your doorman doesn’t count.) And let’s take this one step further. If she’s hashtag-resisting and social-justice-warrioring but at the same time doing whatever she can to ensure her kids enter and remain in all-white schools, get out while you can!
  4. If you have been dating someone for a long time and you’re not sure if your significant other is “the one”, this mental exercise should serve as a test. Pretend you are, or she is, suddenly and unexpectedly pregnant. If your reaction is either, “Yes, that’s great” or “The timing/circumstances aren’t ideal, but we’ll work it out and it’ll be fine in the end,” congratulations! They pass the test. But if the reaction is “Fuck! Fuck! Fuck! Now I’m stuck with this fool!” then no, your significant other isn’t the one. Get out now before this becomes more than a drill!
  5. If you’ve been dating someone for a long time and you’ve never seen them in professional or formal attire, that’s a red flag. Sorry, tech bros.
  6. If you’ve been dating for a long time and you’ve never seen her without make-up, that’s a huge red flag. Sorry, Atlanta women. You can’t know if someone is right for you until you see them looking their worst. Come to think of it, if they’ve never passed gas around you, that’s also a red flag. (Remember we’re talking about long-term relationships here. Keep holding it in for the short-term hook-ups.) If you find yourself wiping the crust out of her eyes before making love to her in the morning, ding! ding! ding! You have a winner!
  7. And finally, if you are sexually active and meet someone who doesn’t believe in premarital sex, then explain that you don’t believe in pre-sexual marriage, and politely bid them farewell. Trust me, you’ll save yourself a lot of trouble later. Not that there’s anything fundamentally wrong with abstinence or promiscuity — to each their own. But life is too short and there are too many people in the world (especially in New York and other major cities) to try to fundamentally alter your lifestyle for someone.

And with these little tidbits, I wish you all the best. While I really had a lot of fun dating and have so many funny stories to show for it (many of which I occasionally annoy my wife by continuing to retell), I’m glad to be out of the game.

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