A Lesson in Rejection: Why You Should Ask Her Out Anyway


  • Backstory: In early 2011, I wrote this open letter, or sorts, on Facebook. I shared it with my friends and eventually, one of them that was working with Creative Loafing contacted me and asked if they could use it on their site. It was the first and only time I had something written and published until this blog debuted this year. Looking back, I realize this letter is pretty much the introduction to my current writing style. It’s open, full of lessons, honest and pretty embarrassing, but hey, that’s how I roll. Keep it real! Anyways, once the letter made it to Creative Loafing, it was edited a bit for their site. Below, I’ve pasted in my original letter, the way I wrote it, as well as the Creative Loafing link. While I have grown a great deal in the past few years, this lesson is forever on my heart. I hope it can help yall too!

So I asked a young lady out. I figured she might say no but felt it was worth trying for. She surprised me with an acceptance, though I could tell it was tentative. Ultimately, she waited a day before declining. Quite diplomatic of her, haha! I figured she’d hang up on me! Anyways, for some reason, her rejection remained on my mind. It finally occurred to me that I wanted to share how I felt about this. Not so much how I felt about her rejection, but rather, why it mattered so much.

In 2010, I made a decision to begin winning the battle against my own insecurities. To shed my emotional shell. Slowly I’ve taken steps toward dealing with the things that scare me or make me uncomfortable. Though this was not the first time I’d ever been turned down for a date, it was the first time that I just flat out asked someone I wasn’t sure would consider me. And it was the first time I’d ever allowed myself to dwell on how it made me feel.

My Lesson: Like many, I have a healthy fear of rejection. I’m always bitching about how hard it is to date, but honestly, I have to lay claim to at least 45% of the blame. (Yes that’s all I’m claiming, lol.) The fear of rejection has taken over me countless times throughout the years, and I can’t help but feel I’ve missed out in the past by letting it paralyze me. How many of us have allowed fear to cripple our interactions? How many of us are alone because we’re waiting on someone to talk to us, who are probably just as nervous as we are? I know beautiful women that go into a club looking fantastic, and walk out thinking they are not up to snuff. No honey, you were just as fine walking into the club, as you were walking out. There are just a lot of scared people out there.

I believe there are at least 5 nervous people for every 1 Lothario. Drunken hookups exist for a reason. It’s HARD to walk up to someone and go for it—period—let alone sober. I’ve been nervous to ask out a woman that I KNEW liked me. Imagine someone new, or someone you really don’t know well, or someone you may believe would never date you. Absolutely frightening.

And it’s even harder if you’ve offended her at any point. Yeah. I’m prone to that. But I digress…

I fell for someone HARD in college. Whew. I still might marry that girl. Anywho, to keep a long story short, I was always too afraid to take that leap and display my true affections. As such we remained in that weird friend limbo many are so unnaturally fond of. It would be years before we actually hooked up. And by then, life was moving for both of us and we’ve never been quite able to align our stars. It remains to this day, one of my greatest regrets. Today, I’m ready to admit that I’ve yet to break this cycle of fear. For every one date I’ve had, how many more could I have had if I wasn’t over thinking it all? Snakes are scary, and they can kill you. Rejection is not a snake. Case closed. I am over being fears hostage.

Sometimes you have to take a leap, even if you think you’ll fall hard on your face. That lingering ball of self-doubt pooled in the pit of your stomach may very well keep you from the love of your life. Have you ever seen a busted chick with a really fine woman? I’m talking bout, she’s looking like death runneth over with a school bus and holding the hand of a grinning Beyonce? Yeah, she probably had the cajones to ask her out while you were standing there drooling and not speaking. Ultimately, I’d rather be rejected than miss out on a good thing. You remember the rejection for a few days, but a great hookup/relationship lasts a lifetime. I’m proud to say I ignored my fear. And I should hope I can remain so fearless in the future

Now, I just have to figure out how to recognize the RIGHT woman to leap for. Haven’t quite figured that one out yet…LMAO! Hey, I’m a work in progress ok? This shit like chinese arithmetic! The rent too damn high. The gas too damn high. The women too damn difficult. I need a freakin lesbian GPS over here!

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