Part IV: It's a Date!


After weeks of interviewing, styling and headhunting, matchmaker Amanda Rose of Prestige Connections has found a date for each of our anonymous singles, Reagan and Juan. 

Reagan’s match is still being finalized. Rose has narrowed it down to three potential matches and has chosen one to interview for a final time and hopefully set up a first date with. 

By the time this story gets in the hands of our readers, Juan will have already been on his first date with his chosen match. We won’t get to hear about it until next week. However, we did sit down this week with Juan and Rose ahead of the date for a little pre-date pep talk. 

Juan’s date, we’ll call her Emily, was found by Rose on LinkedIn. Rose said she and Juan have similar personality traits and similar goals in a relationship. 

“I picked her because she is super friendly and bubbly,” Rose said. “Since this is Juan’s first experience with a matchmaker and he’s really not sure what to expect, I thought she would be perfect to ease the evening. She’s so easy to talk to. They’ll have fun, no matter what.” 

Rose decided to keep things nice, yet casual for the pair’s first date, so she set them up to meet for cocktails at Artillery in Downtown Savannah. She said she chose Artillery because it has a swanky, historic, romantic atmosphere. 

“Nothing too serious, no dinner,” Rose said. “If they hit it off, they can keep the date going.”

Ahead of the date, Juan only knew Emily’s first name, a vague idea of her job, and the fact that she has a pet. Rose said she purposely leaves out details about all of her matches because she hopes the two ask lots of questions about each other. She also said she “doesn’t want people to overthink things.”

Juan and Emily hadn’t even seen a photo of each other, so Rose suggested that Juan bring flowers or the book he’s currently reading on the date so that Emily can easily spot him. Juan decided to bring Jay Shetty’s “Think Like a Monk” for his name tag. 

Rose also advised Juan to go into the night with an open mind. 

“Y’all both have great personalities,” Rose said. “I suggest going into it thinking, ‘What can I learn that’s great about this person?’ Instead of fear or any negative thoughts.”

Juan seemed to have no problem keeping a positive attitude ahead of the date.

“I’m excited,” he said. “In the beginning, I was nervous. I’ve never done this before. Now I’m fully confident and I’m excited about it. This whole process has been really awesome.”

He joked, “If it goes south for any reason, I’ll somehow find a way to have fun!”

Next week, Connect Savannah will sit down with Juan after his first date with Emily and get all the details. We’ll learn if the two hit it off, if they exchanged phone numbers, and if they plan to see each other again. We’ll also have more details on Reagan’s final match and her upcoming first date. 

Where’s your ideal first date spot around Savannah? Let us know on social media @connectsavannah!