The intent of this monologue was to bring emotional depth and realism to a moment many people have experienced—the uncertainty of turning a friendship into something more. While the name Colonel Steve Wilkinson is fictitious, the story is based on real events. A close friend of mine, a retired Air Force officer, lived this moment, and I had the privilege of meeting him while deployed in Afghanistan. His journey from hesitation to commitment was something that stuck with me—a reminder that even the strongest men can find themselves vulnerable when it comes to love.
Steve’s story is one of hesitation, self-doubt, and the fear of stepping beyond the comfort of friendship but he also demonstrates some confidence too. After months of small talk and social media interactions with a charismatic waitress twenty years younger, he faced the question so many struggle with: How do you tell someone you have feelings for them?
This wasn’t easy for me to perform because, by nature, I’m a very confident person. I had to deliberately act as if I was stumbling—not just in words but in body language. That meant throwing in “um’s” and “you knows”—the kind of hesitation that naturally happens when someone is nervous. That’s not something I’m used to at all, but it was essential to capture the realism of a romantic confession. Because in real life, when you’re standing in front of someone, putting your heart on the line, the words don’t always come out perfectly.
This monologue captures that raw uncertainty—the nerves, the weight of the moment, and the hope that maybe, just maybe, she felt the same way. And in real life? That moment of courage led to a beautiful marriage that still stands strong today.
Feedback and criticisms are welcomed! I’d love to hear your thoughts on the performance, the realism, and what you think makes a romantic confession feel truly authentic.
https://youtu.be/gukQp3aNsyc?si=s3MTH72w6ZQHdLnV