I Let My Dad, My Boss, and a Dating Expert Dress Me for a Date

"It will be easy," my boss said. "Just put yourself out there." I spent six and a half of the past seven years in a serious relationship, and dipping my toe back into the dating pool has been painful. So when I found out I was being tasked with going on not one—but three—first dates, I inwardly cringed (no surprise there). But luckily I had a team in my corner to help me conquer one major task: figuring out what to wear.

In the name of journalism, I enlisted the help of my father, my boss, and a dating expert to break down their ideas of the ideal first-date look. But before you draw comparisons to Kate Hudson's character in How to Lose a Guy in 10 Days, I want to make one thing clear: This experiment was more about gauging my own internal reaction to what I wore. Yes, the way the date progressed was important, especially when my outfit picked up a compliment or two. But at the end of the day, my goal was to find the date-night look that best impressed me and my date. 

With admitted hesitation, I got busy navigating the murky waters of dating apps and friend-of-friend setups—all of which actually went pretty smoothly (and I'm sure most of you could have told me that, dear readers). In total, two margaritas, three sauvignon blancs, and one fancy, fruity cocktail were imbibed, and this dating-world rookie learned a lesson or two along the way (thanks to my mentors, of course).

So with three dates down (thanks to Tinder and the friends who set me up), how did things play out? After testing three very different looks, I learned that even though what you wear is important, it's mostly about how you feel in what you're wearing that counts. If I was confident in my ensemble, that is what my date really noticed. Still, let's not pretend testing out three mystery outfits wasn't tons of fun. 

Read on to see how it all went down.