A Local's Guide to Date Night in Winston-Salem

Finding time for a little romance in a new city can be fun and exciting if you know where to go and what to do. Who better to curate that experience for you than the people who live, work and date there themselves? Six local couples share their favorite places and inspiration for visitors looking to spice up their romantic lives and try some Winston-Salem treasures.

CLOCKWISE FROM RIGHT: Maddie & David Bowen, Stephanie Tyson & Vivian Joyner, Greg & Molly Keener, Jacinta White & Everette Funches, Joy & Jasper Thomas, Bria Stark & Nikitas Adamopoulos

David Bowen and Madeline Fox

Where do you go when you own the spot where so many couples like to on their date nights? Bowen and Fox, owners of easytalk, an all-day beverage joint (think coffee by day and cocktails by night) are used to crafting date night experiences for others. But what about when they need couple time for themselves?

“As bar owners, we enjoy having our weekends land on Tuesdays and Wednesdays, when some of our favorite spots downtown are a bit quieter and offer some great specials,” says Bowen. “Picking up a pizza at Brothers Pizzeria and sipping our way through the extensive whiskey collection and $5 whiskey sours at Tate’s Craft Cocktails checks all our boxes.”

And when they are feeling fancy, their favorite thing to do is catch a movie at a/perture cinema and dinner at Sweet Potatoes.

Jacinta White and Everette Funches

It’s not surprising that date nights for this creative power couple is as adventurous and multifaceted as their artistic endeavors and interests. White is a poet, editor-in-chief of Snapdragon: A Journal of Art & Healing, and certified corporate trainer and facilitator. Funches is a mixed media artist, jazz percussionist, and a supervisor at Winston-Salem State University.

For a chill night or day out, they frequent arts events like ART CRUSH and Gallery Hops in the Downtown Arts District and opening exhibits at SECCA. They’re also regulars at downtown restaurants and bars like 6th and Vine, Whisky Box, Tate’s Craft Cocktails, and Top of the 4th, a rooftop bar at the Courtyard by Marriott on Fourth Street.

Their unexpected date night option is Burlesque at Camel City Playhouse for an “entertaining, talented and sexy show.”

Bria Stark and Nikitas Adamopoulos

This couple relocated to Winston-Salem in 2022 from Chicago for Stark’s job as a pelvic floor occupational therapist. Adamopoulos, a design engineer for Honda Aircraft Company, is Greek. Sometimes their favorite date spot is home. They like to hit up the Greek Village Market for authentic ingredients to make his family recipes. “Food is his love language,” Stark says. “We get freddo espressos (similar to frappes) every time. It reminds my husband of his childhood in Greece, and they are addictive!”

For a night out, they enjoy Theodore’s Bar & Market for drinks and apps. “We love their eclectic vibe, and the drinks are pretty good.” They also frequent Lesser-Known Beer Co. and East of Texas after antique shopping at Stone Soup Vintage or L’Avenue Boutique.

Stephanie Tyson and Vivián Joiner

As proprietors of Sweet Potatoes, a popular restaurant in the Downtown Arts District, Stephanie and Vivian don’t get the chance to do too many date nights. The couple opened Sweet Potatoes along Trade Street in 2003, and they’ve spent most of their days and nights there over the past two decades, with Joiner managing the front of the house and Stephanie, a two-time semifinalist for the James Beard Award, running the kitchen.

“We’re kind of boring, we know,” laughs Joiner. “But after 38 years [together], the fact we still enjoy talking and spending time together is huge after working together for so many years.”

That said, “We have found a couple of places that are comfortable, easy, and fit our schedules,” Joiner says. Their regular spots include OH’ Calcutta for dinner, easytalk for drinks, and the Downtown Strollway for walks.”

Joy Nelson Thomas and Jasper Thomas

As parents of a young son, date nights are often a family affair for these busy parents. Joy is the founder and executive director of LEAD Girls and CEO of New Journey Management Group. Jasper is owner of EVO Wellness and Nursery LLC. As entrepreneurs and community leaders, they like to spend their downtime together. “We love lake time at Belews Lake,” Joy says. “And since we have a 4-year-old we spend a lot of time in kid-friendly environments — anywhere with arcades."

If they’re able to snatch a few hours as a couple, they’ve got a few evening and daytime spots. Their romantic night-out spot for two? Bernardin's Restaurant, an upscale spot in the historic Zevely House with one of the best patios downtown. As for daytime dates? “Sometimes our dates look like me shopping and him saying ‘Yes, that looks good' at local boutiques. Sometimes it's a lunch date at Yama's Mediterranean Street Food while JT (their son) is at school.

Toni Tronu and Robert Pennington

When they’re not parenting their lively toddler, Iris, and their 11-year-old basset hound, Merlin, this creative couple is in the throes of juggling family life with their careers and art and musical interests.

Pennington is a marketing professional with Deloitte, and Tronu is the owner operator of the downtown gallery Visual Index and the founder of ART CRUSH, monthly block party in the Downtown Arts District. sometimes keep their dates hyper local — just steps from Tronu’s gallery on Trade Street. They love Chad’s Chai for day dates. “I get a pot of Finnegan's Wake-up, and Robert loves their Chai Latte,” Tronu says. “The ambiance is so nice and inviting.”

Special date nights are for nice meals and cocktails. They might go for an upscale dinner spot like Mozelle’s or enjoy the casual vibes of Finnegan’s Wake. And depending on the amount of time they have and their mood, they might go for a classy cocktail at Joyner’s Bar or opt for the dive bar scene at a place like Silver Moon Saloon.

“This stage of our collective family life is so busy, so dates might just be grabbing a drink somewhere quick so we can take a breath and catch up,” Tronu says. “But if our amazing babysitter can stay late, we might catch a movie at a/perture cinema or see a show at a place like Monstercade."

Molly and Greg Keener

These food and culture enthusiasts love that Winston-Salem is large enough for diverse dining options and cultural events, but small enough to feel like they’re part of the community. Molly, a director at Wake Forest’s Z. Smith Reynolds Library, is a Winston-Salem native. Greg, program officer at the Shallow Ford Foundation, moved to the city in 2002 after several years in Greensboro.

“We go on a fair amount of day dates, often spontaneously, to just knock about and enjoy being together,” Molly says. “We might browse books at Bookmarks or pop in and out of galleries along Trade Street.” (They add that Visual Index and Piedmont Craftsmen are two favorites).

They also like to go treasure hunting along Reynolda Road at spots like Elizabeth's at Hanes Park, Idlewild Interiors, and The Boho Depot to accent their eclectically styled home. (Another favorite spot for vintage finds, they say, is Your Home Marketplace, a multi-vendor mall off Stratford Road.) For special occasions, the River Birch Lodge is their go-to for birthdays, anniversaries, and holidays.

Looking for other places to explore? Check out the Things to Do section of our website for trip ideas, events, and other experiences.

 THINGS TO DO