Ben and Cassie

17 Nov, 2012

by Jenna Kashou

Ben and Cassie know a thing or two about weddings. On their second date, they DJed a wedding. Combined, they have been to over 250 weddings. As you can imagine, they had a pretty good idea of what they wanted for their own wedding before Ben even popped the question.

Cassie is the sister-in-law of Ben’s good friend. They met when she started working for Sound by Design and they hung out for about year while DJing before Ben asked her out.

Cassie and Ben blissfully happy

So here is the part you all want to know – how did he propose? It was an intricate cat and mouse chase that sent Cassie on an “errand” for her boss delivering a package to the Anaba Tea Room. Little did she know,  Ben would be there waiting on the rooftop and her engagement ring was actually inside the package she was supposed to be delivering.

“We knew we wanted to get married almost right away, it was just a matter of timing. We had been talking about it. I held on to the ring for a month before I decided the perfect way to propose because I wanted to surprise her,” admits Ben.

Anaba shut down the rooftop so Ben could light some candles and be alone with her when she arrived.  “She found me up there and knew right away what was going on,” he said. Of course, Cassie said yes.

The plan almost didn’t work though when a coworker offered to drop off the package for her since she was going that way. Luckily the boss intervened and insisted Cassie hand deliver the package.

Ben took her to dinner at Bacchus that night and  surprised Cassie again by arranging for her family and friends to meet them at Blu for a celebratory drink.

“It was a super overwhelming day. I was so anxious and nervous. This is the best part of the day now that she said yes – I can finally relax,” Ben exhales.

Now all they have to do is worry about finding a date and a venue for a June wedding in Puerto Rico. Something tells me wedding planning will be cinch for these two.


About the author

Jenna Kashou

A Milwaukee native and freelance writer, Kashou has published in local publications such as Milwaukee Magazine, M Magazine and the Shepherd Express. Find her weekly adventures of city life as's ‘Girl About Town.’ Kashou earned a bachelor’s degree from the University of Iowa in mass communications and Spanish, and a graduate certificate in digital storytelling from Marquette University. By day, she is a grant writer for Radio Milwaukee and has worked in the nonprofit sector in arts and education for 10 years. In her spare time, she enjoys dabbling in everything from being a DJ and photography to do-it-yourself deco, yoga and rock climbing.

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