What To Do When You Have a Serious Case of the “What If’s”


This post is dedicated to one of my lovely readers who wrote in asking for some advice about this very question. She’s been plagued with the all-too-familiar “What If”-itis. You see, there’s always that one guy, date, relationship, star-crossed-lovers-passing-on-opposite-train-platforms kind of situation that leaves you wanting more. You have that one momentous connection but then nothing comes of it and you’re left wondering, “WTF If.”


What if I had just said that one thing I held back?

What if I had done something differently?

What if I had suggested a different place or I wore a different outfit or maybe didn’t recite all those “Dumb and Dumber” movie lines? (Oh, C’MON, who doesn’t love “Dumb and Dumber”?!)

What if, what if, what if.

We all know that it’s counterproductive to spend your precious hours and beautiful brainpower worrying, wishing, and wondering “What if?” You’re smart, you get it. There’s nothing you can do about it now. It’s worked out exactly the way that it should.

But that doesn’t help the Whitney Houston-inspired, “I get so emotional” side of your mind. That doesn’t quench your desire to know why and what happened.

Here’s the really crappy answer, and I’m giving it to you Vin Diesel-style—fast and furious and first—so we can get it out in the open and then move on to the fluffier answer: You may never know for sure.

MOVING RIGHT ALONG. Even if this is true, here’s what you CAN focus on instead: What you absolutely LOVED about him.

Wait, why would that make you feel better? Wouldn’t that only make you miss him more?

Check it: Homeboy obvi had some lessons to teach you, even if he was only around but for a fleeting moment.

When someone turns you upside down and inside out (I feel a “Whoop (There It is)” recital coming on, but I’m going to restrain myself…), it’s because you needed a good shake up in the self-awareness department. Something needed to be brought to your attention. Nothing like a magical moment with an easy-on-the-eyes guy to make you stand at attention.

Maybe he highlighted a destructive pattern in your dating history. Maybe he showed you what you truly wanted. Maybe he reminded you that you are worthy and totes awesome. Perhaps he just made you feel beautiful again. Or reinstated your faith in your own wittiness and conversationalist connoisseurship.

Do not lose sight of this just because it didn't pan out.

You may feel like it backfired, but it didn’t. You just need to refocus. Zero in on that for-real feeling. That knee-knocking, soul-stretching, I-can’t-live-without-this thing that he did for you. But—and this is vital—don’t get attached to the outcome. Meaning, he is NOT the only one out there who will make you feel like this. The more you focus on how he made you feel, without NEEDING and DYING for the feeling to come from him, the easier you will open up to the possibility for another satisfying sir to enter your life.

There is a damn fine reason he wasn’t meant to stick. Swearskis. Let us be real: he probs had major emotional obstacles to combat anywho. Otherwise, who would have left you in a lurch after a consciously connected smooch sesh like that? Agreed? Whatever the reason, I know for sure that you dodged a boys-issues bullet.