Mike and I had been planning this Paradise Island surprise proposal for at least two months. From the start, he made it clear—this had to be perfect. Every little detail mattered to him. And then came the twist… he didn’t just want beautiful still photos, he wanted the emotions captured on video. This was going to be tricky—nailing the setup, the photography, and the video without giving the surprise away.
I knew right away I’d need help. That’s when I recruited Tonya. She’s sharp, quick on her feet, and I trusted her to help keep the whole thing running smoothly.
One major part of the plan was getting clearance and permits from the Warwick. That alone could have been a headache, but planning went surprisingly well. Imani at the Warwick was fantastic—helpful, cooperative, and she understood the importance of keeping everything under wraps. On paper, the execution was airtight. But we all know how life works—sometimes it likes to throw you a curveball.
Fast forward to the big day. Tonya and I arrived early—way early—just in case something unexpected popped up. And wouldn’t you know it, the first hiccup hit before we even got started. The concierge at the front desk had no idea what was happening. Apparently, Imani hadn’t passed along the details. Because this was a surprise, we’d intentionally kept the plan to a small circle, but without Imani there to confirm, the front desk was skeptical.
I had to call Mike to come down and help smooth things over. But that created another problem—Mike was gone longer than expected, and Kelly started wondering where he went. Next thing we know, she’s heading for the lobby looking for him. Mike had to literally hide. I sent Tonya over like a secret agent, telling her, “Compliment her sunglasses, say something nice, stall her.” And it worked. They chatted briefly while Mike and I ironed out the new plan.
Originally, the idea was simple: Mike and Kelly would have a complimentary dinner on the pier. I’d walk up, offer them a free photo session, Mike would initially say no, I’d insist, and he’d finally agree—cue the setup for the proposal. But the deck area was crowded with Warwick guests, so that idea went out the window.
Time for Plan B. I approached Mike “as a hotel staff member” offering a voucher if they participated in a quick video survey. Mike did his part, acting resistant. The only hitch? Kelly was also resistant—“No, we’re on vacation, we just want to relax.” But my guy Mike knew what to do. He turned to her and said, “You know what, baby? Let’s do it.” Smooth.
We walked them over to the pier, pretending to set up for the “interview.” Mike was nervous—I could see it in his eyes—but he kept his cool. I got Kelly focused on the lens, giving her instructions to keep looking at it while Mike quietly positioned himself behind her. Then came the moment of truth.
“Okay Kelly, just turn around real quick,” I said. She turned slowly, confused, like Where’s Mike? Then she looked down… and there he was, on one knee, ring in hand, smiling with a proposal so heartfelt I almost forgot to keep filming. Kelly was speechless, tears welling up, and the people nearby caught on fast. The pier erupted in cheers. She finally said “YES!” And then someone in the crowd yelled, “You guys are gonna be making love tonight!”—which, for the record, was none of my business.
The only little hiccup? The ring didn’t fit quite right, so they’d have to get it adjusted. And Kelly, now all teary-eyed, wasn’t prepared for a photo session without makeup. No problem—we agreed to meet again two days later for the official engagement shoot.
Mike, thanks for letting me be part of your love story. Another surprise proposal pulled off… and my undefeated streak lives on.
