#FearlessFebruary: Just Say “Yes,” Please?

12 Feb

For this month’s Calendar of Courage challenge, I decided to ask a close friend of mine out on a date. I know what you’re thinking “Oooh Maddie, no dating in the friend group”! I’ve been told this about a thousands times by my closest girlfriends but I was willing to give it shot!

I’ve known him for quite some time now and I can admit I’ve developed a little crush on the guy. I thought about the repercussions in asking him out, and my fear and anxiety grew by the second.

dont freak out

Then came the what ifs…

What if he says no and I have to grin and bear it?

What if he thinks I’m weird and we won’t be as close anymore?

Should I text him? What if I ask him face-to-face?

What if I have something on my teeth and he won’t pay attention to what I’m saying and I have to ask him again?!


Okay, so the what ifs didn’t help. For a week I thought of ways to ask him. They ranged from calling him during a random time (you know, the casual approach), texting him a cheesy quote and then casually asking, or setting up a time we just so happen to run into each other at 1:15 on a Friday afternoon…

Now if you haven’t noticed already, I’ve thought this through for quite some time.  My words had to be precise and clear. I was stuck between saying “date” or “hangout”. I didn’t want to scare the dude by labeling it as a date (although I was leaning towards it). But at the same time I didn’t want him to think it was just a casual night where we go get greasy, delicious food.

Time definitely  was not on my side. I had to act and think fast, before that one “lovable” holiday came around.

V-day Urkle

The big day finally came around, the day I was going to ask him out and do it flawlessly. My hair was on point, and so was my outfit. I even saved some gum to avoid stank breath.

Once I build up the courage I texted him asking him where he was and if he could meet me by Modern Languages. Preciseness, my friends, preciseness.

I waited…


Finally a response! We talked about nonsense for awhile then I popped the big question… I asked him where he was and when I could meet up with him in person.

Long story short we kept rescheduling a time when to meet but couldn’t cross paths. Although I wanted to ask him in person, I ended up texting him again later on that night and asking if he’d like to go out on Saturday for some sushi.

Luckily he answered quickly. Not so lucky, he politely denied my request. At first I was a little salty, but then I realized our friendship is worth more than a bitter moment.

I must say I wasn’t upset over this experience. In fact I was pleased with myself for having the guts to ask him out in the first place. Rejection is not always a bad thing, believe me. You have to push your limits sometimes to see how far you’ll go.

As for my Valentine’s Day plans, let’s just say Brooklyn’s Pizza should be expecting an extra large order of pizza and garlic knots.

Until next time,

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