Behind the scenes of the CHScupid blind dates

Screen Shot 2019-02-13 at 10.20.47 AM

Photo by Prohibition Charleston

Table of Contents

Happy Valentine’s Day, Charleston! With today being all about making a love connection, we know y’all are on the edge of your seats wondering how the #CHScupid blind dates went.

The Bachelor .gif via giphy

If you’re just tuning in– last month, we asked our readers to send us the most eligible bachelors + bachelorettes in Charleston. After sifting through nearly 100 applications, three couples were chosen by y’all’s votes to meet for a blind dinner date– courtesy of Prohibition.

So how did the dates go, you ask? We met each couple at the door to help introduce the pair– then left them to take it from there.

After their date, we followed up with a short Q+A asking how the evening went. Here are their post-date reactions.

The pairs:
💕 Shayna + Tim
💕 Kelsey + Juan
💕 Jessica + Andrew

Did you Google your date before meeting? If so, did you tell them once you met?

Shayna: Nope, I kept it all a surprise!
Tim: No.

Kelsey: I did not google them. All my friends tried to, but had no luck finding him. I did tell him that!
Juan: No.

Jessica: Nope.
Andrew: No and no

What was your first impression of your date?

Shayna: Nice smile, dressed well, kind.
Tim: She’s independent.

Kelsey: He was very chivalrous. He immediately complimented the way my outfit complimented me.
Juan: Attractive.

Jessica: I was pleasantly surprised! I didn’t go into it with high expectations, but he was handsome and warm which put me at ease when we first met.
Andrew: Attractive and sociable.

Describe the person in which you were matched in three words.

Shayna: Friendly, engaging, reserved.
Tim: Educated, talkative, foodie.

Kelsey: Gentleman, confident, affable.
Juan: Athletic, personable, and ambitious.

Jessica: Genuine, kind, easy-going.
Andrew: Beautiful, humble, caring.

How would you rate the evening on a 1-5 scale, 5 being the best date of your life?

Shayna: 3
Tim: 3

Kelsey: 4
Juan: 4

Jessica: 4
Andrew: 4

What happened at the end of the date– did you exchange numbers? Go anywhere together afterward?

Shayna: Exchanged numbers.
Tim: We exchanged numbers.

Kelsey: We exchanged numbers.
Juan: Exchanged numbers, walked with her, she went home and then I went to eat pizza haha.

Jessica: We exchanged numbers.
Andrew: Paid for dinner but stayed for another drink. Kiss on the cheek once we left.

Would you consider going out on a second date? If yes, do you already have plans to see each other again?

Shayna: Sure! No plans right now.
Tim: I would consider going out again.

Kelsey: I would consider another date.
Juan: Sure.

Jessica: Yes, for sure. I really enjoyed talking to Andrew and learning more about him. He’s a great guy.
Andrew: Yes.

How was your experience at Prohibition? Was it a good place for a first date? How was the food/service?

Shayna: Prohibition was excellent– food and service were awesome!
Tim: Great drinks, food, and service. It was a wonderful experience.

Kelsey: Prohibition was a great first date place. Food was delicious, service was great and the live music was a great touch to end the evening!
Juan: Great first date location– food was delicious, and service was pleasant.

Jessica: For sure, you guys did a great job– everything was on point and the food and drinks were amazing. Thank you very much for the opportunity! I’ll definitely be going back.
Andrew: Prohibition was great all around.

While all three couples said they had a fabulous time, some did disclose that they weren’t sure if there was a romantic connection. So while we won’t hold our breath for any wedding invitations– we’re glad to have at least help spark a potential flame.

P.S. If you haven’t already been to Prohibition– make sure you head to 547 King St. and check them out… you may just find love there waiting for you (and if not– at least a great cocktail and delicious bites). 💋😋

More from CHStoday
Hit the road and head to Savannah — we’re sharing all the details about what to do and eat, plus where to stay.
The concept is taking over South Korea’s capital city. We’re thinking about where we’d copy it in the Holy City.
Ever spotted the Holy City on the silver screen? We have.
Charleston is among the hottest real estate markets heading into 2026, so we wanted to investigate.
A grassroots effort is helping Lowcountry properties become part of a nationwide habitat network.
Our readers have spoken — here are the best local spots our city has to offer, from the best coffee shop to the best apartment complex to the best dentist.
Bookmark this guide for a curated list of events taking place each month that we’re most looking forward to.
Directly north, east, south, and west, the world awaits.
The 16th annual edition of Small Business Saturday falls on November 29 — the perfect time to help you add a local sparkle to your holiday shopping.
We’ll get it started with a family road trip along Route 66 to Charleston in the 1970s.