Follow up from my OOTD this morning. The proposal went just as planned! She was caught off guard just enough. The gold band is a placeholder for the custom ring we just ordered last week. Plus she said she loved my outfit. Thanks again to all of you for support!

I am a data nerd. I log my outfits every day and developed an AI tool to build an outfit for the next day, including ensuring I don’t wear the same outfit in front of clients or key vendors for the past 5 meetings. I also try to avoid style faux pas. Wearing two watches is an oddity, but I love the data from an Apple Watch and the fit of a nice looking watch. After some simple research, I learned that I could wear the Apple Watch on my ankle. I previously had one of those stretchy elastic bands from Apple, so using that band I put it on and was getting all of the data as if we’re on my wrist. Here’s the crux. The band was not well fitted unless one likes a tourniquet. After a few days, my ankle and foot swelled up. When that didn’t recede after removing the Apple Watch for a few days, my podiatrist sent me to the ER. The ER found that I had developed a blood clot and required a 24-hour stay to break it up and 9 months of follow up treatment with medication. The lesson is not don’t let fashion kill you. It is absolutely don’t be an idiot… oy vey.