I've never been the smoothest guy in the world.
In high school I accidentally told a girl I loved her and then said I was kidding to cover up my embarrassment.
I've unintentionally made a joke about a girl's recently deceased grandfather.
I've attempted to ask a girl on a date from a stage in front of 1,500 people only to find out that she wasn't even in attendance.
And one time I even emailed my niece's math teacher under the pretence of asking her 'a math question' in hopes of getting her number so I could ask her out. Let me tell you: there's no challenge quite like sending an email to someone you've only met once in passing, asking for their phone number so you can ask them out on a date . . . talk about tiptoeing the fine line between friendly and creepy.
But it’s awkward
I was talking to my nephew* recently about a girl. This is a girl that he goes to school with, and more importantly, a girl that he thinks is really cute. I asked him if he had talked to this girl or was going to talk to her in the near future. He just responded, 'No, that would be awkward.' He liked this girl, but he wouldn't talk to her because of a fear that their first conversation probably wouldn't go that smoothly.
This isn't just about dating; I think that a lot of us guys have become so afraid of awkwardness that we never take risks. We're not sure how we might appear if we take a stand for our faith, so we keep silent when the Church is mocked. We know that we're not perfect ourselves, so we feel too hypocritical to challenge someone else for something that they're doing or saying that is wrong.
The road to greatness is paved with awkwardness.
We've got to be willing to take risks, we must be ready to put ourselves out there if we want our lives to count. Imagine if the early Church had kept silent for fear that they would be shunned by society for preaching the Gospel. Imagine if the Saints had let the fear of being different keep them from radically living out their unique vocations. Who knows how many souls wouldn't be saints if they let their fear of looking weird overshadow their desire to follow God.
The fear of failure
I wish I could say that every risk has a good ending, but that's not reality. The good news is that really awkward experiences make for the best stories later on (if you're really lucky, someone caught the mishap on video).
But don't let the fear of failure hold you back from taking risks. Ask God for the courage to stand up and remember that nothing worthwhile comes without taking a risk.
Trust me, sometimes those risks really turn out well. Despite a weird introduction, that math teacher emailed me back. We got married in April and we're expecting a little girl in February. Thank God for awkwardness.
*At last count, I have approximately 18 nephews. To protect the anonymity of this one, we'll just call him Matthew.