A first date can be incredibly hard to pull off. Plan it out too much and it comes off as creepy, but flying by the seat of your pants is almost a guarantee for disaster.

We recommend a loose plan, so you don’t end up driving aimlessly. Ideally, the setup is dinner, event, scenery and the potential for a nightcap.

Beach
Taco Lu
Taco Lu
Bar area inside Taco Lu
Taco Lu 10 Dollar Taco
Taco Lu Bangin Shrimp Taco
Mural outside Taco Lu
Players by the Sea
Players by the Sea

Start the night off at Taco Lu (tacolu.com). Although they don’t take reservations, they can text you when your table is ready. They have a fantastic outdoor area with several open bar areas. There’s a massive mural splayed on the side of the building that is great for breaking the ice and the whole restaurant explodes with color. Their tacos are big enough to share, but small enough to get a variety. You order each taco individually and they have an interesting menu. The Baja Fish taco is deliciously crunchy: the beer battered mahi-mahi is mild and gives the flavor a great background. The Bangin’ Shrimp taco is great for people who love sauces. Many restaurants do some variety of the “Asian fried shrimp,” but Taco Lu has it down to a delicious, tortilla-wrapped science. Finally, their Ten Dollar taco doesn’t really cost ten bucks, but, with slices of tender filet mignon and two different kinds of cheese, you’ll know how it got its name. Once you’ve impressed your date with your culinary adventurism, without dripping sauce down your chin, you know you’ll make it to a second date.

After dinner, head over to Players by the Sea (playersbythesea.org) for some community theatre. This class act local company was founded in 1966 and hasn’t stopped bringing down the house since then. From Broadway revivals and comedies to political dramas and tragedies, Players by the Sea is a mainstay in the Jacksonville theatre scene. Their main stage is cozy enough to make you feel like you are part of the scene while still maintaining a classy theater experience.

Once you have eaten and been entertained, there’s nothing better than a moonlit stroll down the beach. Be sure to find one of the public access points and shuck your shoes because there’s nothing better than the cool rush of seawater between your toes. Take a little time to appreciate both the moment and the company.

Not ready for the night to end? Check out these additional nightcap options.