Grace, 21, Far Northwest Side

“Pizza was the subject, and his strong opinions won me over. Right off the bat, I knew that we had a few things in common—school in Connecticut for one—and that he had a good sense of humor. He suggested we test out Chicago’s new claim to fame, Great Lake Pizza, recently named the best pizza in the country by GQ magazine. I appreciated his enthusiasm and original date idea and agreed to meet him on a warm Wednesday night. He was charming and thoughtful, making sure we didn’t have to wait and that we got a seat outside (a hot commodity at a restaurant that has only a few tables). Conversation flowed, and the more we spoke the more I realized that maybe this blind-date thing wasn’t so weird. Even at the end of the date I was still a little wary of the whole dating via Time Out, but when he declared Great Lake not quite as good as our Connecticut faves, I couldn’t help but laugh and forget about the unusual way we met. Future dates were planned and executed, and we may even have a New York pizza date in the works. I owe Time Out big thanks for finding me the perfect summer fling!”

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Grace | Lindsay | Matt | Phillip | Jonathan | David | Elizabeth | Christina | Michael | Monica | Fling sting | Paging doctor drunkard