Love Tips from a Divorcée: Lesson 3: Play It Cool, Motherfuckers

Very little of my adult life has been spent in the dating world. My MO has been to hurl myself from one relationship to the next, leap frog style. Here’s a breakdown of my relationship status over the past 15 years.

Relationship Status 15 Years

Footnote: Long distance relationships get their own special category because it’s kind of like being single but with an emotional security blanket.

Trust me, therapists have a field day with that diagram. Let’s examine why you can’t be alone, Sarah. Are you afraid that if no one is around to witness your life and compliment your hair, you’ll cease to exist? It would explain the blog.

Due to my inexperience with dating, my advice series thus far has focused on the relationship side of love. The relationship books I’ve read do the same, glossing over the messy business of courtship in favor of the messy business of partnership. The attitude seems to be that people are pathologically drawn to each other against their will, so let’s focus on helping them not destroy themselves when it happens.

There is, however, one piece of dating advice I do have: Play it cool, motherfuckers. Play. It. Cool. From the little I’ve seen, people seem to screw it up by being overly anxious in the beginning and appearing desperate. Or they swing too far the other way, too freaked out to even approach their love interest. Common denominator = not playing it cool.

There is a tiny element of nuance to this rather obvious advice, so hear me out. Playing it cools means communicating the following two things to that maybe-special someone in your life:

1. I really like you and think you’re neat.

2. I’ll be 100% A-OK if nothing pans out between the two of us.

For those of you who have a hard time with words, here’s an example you can follow, free of charge:

Pick Up Quote

Taking this advice isn’t as easy as it appears. There are two major pitfalls to avoid.

Pitfall 1: Don’t be an Asshole

First, you’ve gotta learn the art of playing it cool without being a jerk. A lot of people who play it cool overdo the second part of the equation. Instead of conveying that they’d be fine on their own, they communicate that they don’t give a shit about you. They make plans and then flake last minute. They shower you with attention, ignore you, and then just as you’re about to split, they shower you with attention again (and repeat). They play on your jealousy by flirting with or talking about other pretty ladies/handsome men. Basically, they play those agonizing dating games that make singles everywhere conclude that dating is the worst part of the human condition, just above dying.

Human Condition

Because most of us are insecure dimwits, these games are alarmingly effective. Even so, I’m not recommending them because a) side effects include being the object of resentment and bad karma; and b) it’s asshole behavior and we are already up to our eyeballs in assholery in this world.

So, don’t forget about part 1 of the equation. Let your maybe-special someone know that, although you’re just getting to know them, so far you think they’re the cat’s meow.

Pitfall 2: Don’t be a Poser

Now that you’ve learned how to not be an asshole, you need to figure out how to avoid being disingenuous. This occurs when you’re trying to convey the second part of the equation, but you don’t mean it. For this to work, you have to actually believe that you’ll be fine if things don’t work out. Because by and large, people can tell when you’re faking it.

Boy:         If you don’t mind, I want to take it slow for a while. Just have fun, you know?

Girl:          Me too! Anyway, if you were to have a baby, what would you think of the name Madison? Just wondering.

Boy:         You sure talk about babies a lot.

You must genuinely convince yourself that being with this one person isn’t the most important thing ever. Because it’s actually not. I’ll admit that this is tricky when you’re really into someone. If that’s the case, it DOES seem like the end of the world if it doesn’t work out, and it requires having ninja-level confidence and security in yourself to not take it too personally.

I’m forever working on acquiring those ninja skills, and it looks like it’s gonna take a while. But I’m fortunate because my personality flaws seem to work in my favor for once. If you’re one of my roughly 3 internet fans, that means that you’ve read my last post and know that I’m a novelty-seeker. This means that I’ve mastered the first half of the equation – letting someone know that I think they’re neat. I get spastically excited when I meet a new person that I like, and I’m not too shy about letting them know it. At the same time, my “isolator” tendencies make me pretty good at communicating the second half of the equation since, in the beginning, I’m skittish and afraid of commitment. One might accurately point out that this behavior is insane and bipolar since it goes something like, “Hi new person, you’re fantastic and adorable, love love!” …followed immediately by… “Whoa, easy tiger, don’t get the wrong idea.”

In dating, I deal with these competing impulses by erecting barriers to keep a relationship from happening too fast. These barriers usually take the form of an ex I’m still involved with, an ex I’m still getting over, or my pressing need to “find myself.” Mind you, this isn’t something I do consciously as a dating strategy. It’s taken a certain level of introspection for me to be able to look back on my life and recognize the pattern. Also note that I did not claim to be good at accomplishing part 2 of the equation. Rather, I’m good at blocking myself off in order to convince both myself and others that I’m happy being alone. And that’s cheating. Dangit.

I feel like I keep giving advice that I cannot follow myself. I suppose that’s part of the conceit of an advice series written by a divorcée. Do as I say, love monkeys, not as I do.

Featured photo credit: Dean, James Dean By Jlmaral (; Source:


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