Part V: A six hour first date

Connect Savannah has followed along for weeks as two anonymous singles have dated in our city with the help of professional matchmaker Amanda Rose of Prestige Connections. After styling, date coaching, and extensive interviews; Juan has gone on a first date, and Reagan has one planned for next week. 

As we told ou last week, Juan was set up to meet his date Emily at Artillery in Downtown Savannah. What Juan expected to be one or two cocktails turned into a nearly six hour date. Yes, you read that right. Six hours! 

Juan took Rose’s advice and arrived a little early. He sat at the bar and waited for a woman in a green dress to arrive.

“Waiting for her to get there was a little nerve-racking,” Juan said. “When I first saw her, I was like ‘Wow, she’s really pretty’ and she sat down and we started chatting. We were both nervous.”

Juan said like most first dates, it was a little bit awkward at first. He ordered a gin cocktail, and she ordered a Prosecco drink. Once they laughed about neither of them being set up by a matchmaker before, Juan said the conversation picked up. 

The two talked about their pets, their families and their hobbies. They joked about Emily being a picky eater. They even talked about their past relationships.  

“She told me she does the Irish goodbye,” Juan said, laughing. “She said if she doesn’t like something or somebody, she’ll just leave. So I guess that was good news. She stayed for a second drink and we kept hanging out!”

Juan and Emily stayed at Artillery for hours and eventually got hungry. Juan said he wasn’t ready to say goodbye, so they decided to walk over to Hitch for some late dinner together. 

After dinner, Juan dropped Emily off at home. It was nearly six hours since the two began their date at the bar. The two did not share a goodnight kiss (we know you were dying to know), but they did exchange phone numbers. Juan texted Emily later on to tell her he had a great time and hopes to see her again. 

“She’s a very independent woman,” Juan said. “I like that.”

Juan said while the two had similarities, they also had some differences. Juan wears his heart on his sleeve, while Emily admits she isn’t a very emotional person. The two’s social habits don’t align perfectly either. 

However, Juan said he “wouldn’t change a thing” about the date and said he still hopes to see Emily again. 

“I don’t really judge a first date too hard,” Juan said. “There’s no way until you get to know them a little more later on. You don’t tell your whole life story the first time you meet somebody. I would like to have a second date.”

Emily texted Juan back and said she would be interested in seeing him again, but he hasn’t heard from her since. Rose advised Juan to follow up again and see what she says about planning a second date. 

“A six hour first date is almost unheard of,” Rose said. “I’m really impressed.”

Meanwhile, Rose has narrowed down her first date finalists for Reagan to one man. We’ll call him Thomas. Rose said after the final round of interviews, she had no doubt that Thomas was her top pick.

“I was super excited,” she said. “He was telling me about where he is in life and a little about himself, and his answers were so much like Reagan’s. I think they will have a great connection.”

Just as she didn’t for Juan, Rose didn’t give Reagan too many details about Thomas ahead of her date. All Reagan knew is that Thomas moved to Savannah years ago from another state, he has grown children, and he’s divorced. 

Thomas is slightly over the age range that Reagan stated in her profile preferences, but Reagan said that isn’t a problem.

“I’m a little nervous, but mostly excited,” Reagan said. “Amanda is so excited, so I’m into it.”

Reagan is hoping Rose sets up a date with some kind of activity, like a cooking class or axe throwing. Next week, we’ll update you on what Reagan and Thomas did on their date, if there was a connection, and if they’ll see each other again. We’ll also update you on if Juan and Emily will have a second date. 

What activity around Savannah would you set up Reagan and Thomas to do on their first date? Tell us on social media @connectsavannah!

About The Author

Lauren Wolverton

Lauren Wolverton is self-described storyteller, fashion addict and lover of lattes. At Connect Savannah, she is a journalist and a strategic marketing consultant. Wolverton grew up between Georgia and Mississippi, then went on to graduate from Mississippi State University. A job as a news producer at a local television...
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