Is Rejection Worth the Risk?

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I realized I haven’t posted in a while—but I promise to add new content more regularly this coming year. I’ll be starting my MBA in January, but you know what? Challenge accepted.

For whatever reason, I find it fascinating when the Comedian gives dating advice to his younger cousins. It’s not that what he says isn’t valid—it’s that it all makes complete sense. It’s like a window into the male brain. Since we met online, he never had to hit on me at a bar or throw out some cringey pickup line. But hearing his perspective still gives me a deeper understanding of the dating world from the other side.

I’ve spent years being single, dating, observing, laughing (sometimes crying) through it all—and I’ve definitely formed my own theories. For example: I’ve learned to smile when I want someone to come over. To laugh at their jokes (even if they’re bad). And I’ve come to admire what men deal with when it comes to rejection. Society often expects them to take charge, to initiate, to risk the “no.” Women have gotten bolder over the years—thankfully—but I’ll admit: when I’ve taken the lead, I’ve sometimes felt out of place. Too forward. Too masculine.

And let’s be honest: when I’ve approached a guy, about 75% of the time, I’ve been rejected. But when someone approaches me? There’s a 90% success rate for at least a decent conversation.

Now, I’m not saying don’t shoot your shot—by all means, do what works for you. I’ve just learned that for me, it’s more effective to make space for the connection to happen rather than force it. I also try to make the conversation about the other person, not me. The more I know about someone, the easier it is to see if we’re aligned. But again—that’s what works for me.

I said something the other day that felt like the most “me” metaphor possible:

“Dating is like math—there are different ways to get to the answer, but all that matters is you have the correct answer in the end.”

No matter who you are, there’s always a risk of rejection. But don’t let that stop you. There really are plenty of fish in the sea. And if someone doesn’t feel it, that just means they’re not your person.

My best friend once told me something I’ll never forget:

“If he doesn’t get your jokes, he’s not for you.”

And she was right. I have a unique sense of humor—equal parts dry, nerdy, and corny. I needed someone who would laugh with me or at least laugh because I’m laughing. Thankfully, the Comedian gets my jokes. Or at least pretends to, which is almost better.

So here’s my point: if you never take the chance, you’ll never know the outcome. Go for it. Risk the “no.” Because the worst that could happen? She says it. And you go on with your day. But the best that could happen? You find someone who laughs at your jokes—and gets you.

And that’s always worth the risk.