Making a lasting Connection

Our NEW ANONYMOUS DATING SERIES follows two individuals on their quest to make a match

One thing Savannah isn’t short on is date-night ideas. The city is full of great food to eat, beautiful streets to stroll and local artists to see perform. But between tourists only in town for the weekend and Savannah’s small-town, everyone-knows-everyone feel, finding someone to date may be harder than it sounds. 

In hopes of relating to, entertaining, and inspiring our readers, Connect Savannah is following along as two singles navigate dating in the Hostess City. 

We’ve partnered with Prestige Connections, a private matchmaking service for professional singles. Founder and CEO Amanda Rose is a nationally recognized matchmaker, and her business has been featured in Glamour, Forbes, Elite Daily and other national media.

“We represent clients nationwide to help them find the highest quality, exceptional dates,” Prestige Connections said. “All dates are pre-screened, hand selected and matched based on factors that create a long-term relationship.” 

From here, Prestige Connections will get to know Reagan and Juan a little bit better, give them dating advice and styling tips and hopefully find them a match. Stay tuned this month as Connect Savannah follows their journey. We figure there’s only two possible outcomes: our team gives an awesome speech at a wedding one day, or everyone leaves with a really good new dinner-party story.

Our singles will be anonymous, under the names Reagan and Juan. So far, they’ve each taken the first step and filled out their Prestige Connections profiles. Let’s get to know them: 

Meet Reagan

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Age: 43
Gender Identity: Woman
Interested in: Men 

The Highlights: 
Independent, hardworking, likes to have fun, travel and laugh. Interested in special needs advocacy and community outreach, hiking, movies, game nights. Mother to one college student with special needs. Divorced. Christian. 
Relationship Goals: 
A loyal, but not constant, companionship. Someone who is extremely independent like she is with a good sense of humor. Open to a long-term partner. Not interested in marriage. 

CS: How are you feeling? 

R: Nervous. Nervous, curious, anxious.

CS: What are you looking for in a partner? 

R: I need somebody that can match my sarcasm. Somebody that can be both playful and serious; somebody who can be a bit childish at times. I also like to be the boss. That’s my personality all the way around. While I like to be in charge, in a relationship I’d like for it to be an equal playing field. 

CS: What was the easiest question to answer on the application? 

R: My name! It was challenging to fill out the stuff about me, but not as challenging to fill out the stuff about what I want. 

CS: And the hardest question? 

R: “Tell me a little about you.” You have to figure out - in three or four sentences - how do I describe myself? What descriptive words are right for me? You don’t typically think about yourself in a descriptive way.

CS: Tell me a little about your dating history. 

R: In the past 20 years, it’s been very casual. Nothing serious, just dinner here and there. There’s been several first dates and several second dates, but then I usually bail. I bailed because I was focused on my child. Over the last 20 years, I haven’t had a whole lot of experience because of that.

CS: How did you meet people you have dated in the past? 

R: A lot of referrals from friends and clients, some in bars. Now, I don’t want to meet people in bars. That’s for people in their 20s. No dating apps. 

At my age, you hang out with girlfriends who have husbands. And they hang out with other couples. In my younger years, my friends set me up on dates, and it’s not that way anymore. It’s kind of intimidating.

CS: Why do you think your past relationships haven’t worked out? 

R: Honestly, as the parent of a special needs kid, you cocoon everything. You keep a tight knit group to protect your child. If you ask my daughter right now if I’ve ever dated since she’s been alive, she will tell you, ‘No, my mom has never been out on a date.’ That’s what you do. You protect them. I would never let it work out. I would never let anybody in, on purpose.

CS: Looking ahead, if you met the right person, would you want them to be in your life long-term? 

R: Right now, my daughter and I are at the beginning of both of our lives. Marriage is completely off the table; it’s not my thing. But we are just beginning our own separate lives. We’ll have to figure it out.

Meet Juan

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Age: 35
Gender Identity: Man
Interested in: Women

The Highlights: 

Outgoing and extroverted. Interested in fitness, socializing, non-profit work, movies, video games and the outdoors. No children. Never married. Catholic. 

Relationship Goals: 

A partner who wants to try new things with him. Someone funny and adventurous. Hopes to get married and have children one day. 

CS: What did you think about the application? 

J: The easiest question to answer was about what I want. Thinking about yourself can be hard. I’ve never done something like this before, so I was nervous going through it. But those questions do open your eyes to what you expect from somebody and what you really want.

CS: What are you looking for in a partner? 

J: I know that I want to get married and start a family. I know that’s what I want eventually. I’m looking for someone who has a bubbly personality like me. Someone who wants to be outside. I know what I like, but I also want someone who can teach me new things. No one can complete you, but I think I want someone who can add to me and my life. 

CS: Tell me about your dating history.

J: It’s been casual, just trying to find the right person. I’ve also been working on myself and my goals. I’ve wanted to accomplish some things for myself, so that I can focus on finding someone I want to spend the rest of my life with.

CS: What is your love language? 

J: Acts of service, quality time and physical touch. I like to make someone feel special, and I like to feel wanted as a partner.

CS: How have you met dates in the past? 

J: I’ve met people out with friends. I’ve never, ever been on the apps. I tried Tinder for like a week and said ‘I’m done.’ I like the old school way of meeting someone usually.

CS: Why do you think that your past relationships haven’t worked out? 

J: I think it’s because I felt guarded. I put a wall up. I’ve learned that if you go into a relationship with the mentality that it will fall apart one day, then it will crumble. People change, too. In past relationships, we’ve grown to want different things. People can change, and I’ve been on both sides of it.

CS: Do you think that you are open and willing to let that guard down? 

J: Of course. I think everyone wants to find someone that makes them happy, and I’m open to that. This whole process is exciting. You never know what will happen. I think that’s the fun part about it. It’s fun and also serious. Relationships are important to human life. Meeting somebody new is always exciting.

Are you dating in Savannah? How do you meet people and do you run into any problems? We want to hear about all kids of couples! Send me an email at Learn more about Prestige Connections at