Jessica and Michael

How We Met

We met via OkCupid in 2010. I had written on my profile that my guilty pleasure was binge watching Cash Cab. It turns out, he was a contestant on Cash Cab (and even nailed the red light challenge!). It was a match made in a Ben-Bailey-hosting, OkCupid algorithm heaven.

How He Asked

I grew up my whole life competing in pageants. As I got older and began my career, I often joked about starting a pageant called “Little Miss Business” where corporate women would compete and celebrate their workplace accomplishments in a Miss America style extravaganza.

Where to Propose in Hill Country BBQ, New York City

Last June, under the guise of participating in live band karaoke with friends, I arrived at Hill Country BBQ in New York City. As soon as I came down the stairs, he jumped on stage (in a full suit) and began singing, “There she is, Little Miss Business” to the tune of the Miss America theme song. With my friends and family hid in the corner of the restaurant, I didn’t immediately realize what was happening! When I saw his mom peek out from behind a pillar, I realized that this was the moment.

Jessica's Proposal in Hill Country BBQ, New York City

As the host, he brought me on stage for a hard-hitting question and answer portion, which included asking my thoughts on climate change, the current political climate, and world peace. The final question was, “Will you marry me?”. As the winner of the first annual Little Miss Business pageant, I was crowned with a tiara, custom sash, bouquet and, of course, an engagement ring.

The night followed with actual live band karaoke with all of my friends surrounding me (fully decked out in cowboy hats and bandanas) to celebrate our engagement.

Special Thanks

Michael McWeeney
Photographer