Short answer: Jacksonville date nights work in pairs: dinner plus a walk, show plus a nightcap, sunset plus whatever follows. The trick is picking one neighborhood and staying, because the city is too big to cross twice in an evening.
The classic. Dinner in Riverside or San Marco, then a slow walk through streets built a century ago. Both neighborhoods keep their evenings close together: restaurants, dessert and a last drink all within a few blocks, all findable under /directory/?cat=Food+%26+Drink.
The riverfront play. Downtown's riverwalk at dusk is the city's most underrated backdrop. Time it right and the bridges light up over the water while the day cools off.
The beach version. An early dinner at the Beaches, shoes off at sunset, and the long walk where the crowd thins. In summer, the after-storm evenings are the secret: cool, clear and empty.
The wildcard. Trivia night, a pool table, live music: /directory/?cat=Bars+%26+Nightlife carries the loose end of the evening. Check /events before you go; the good nights book up.
Keep score gently. Save the winners in your /become-insider account and rotate. A city of a million people should never give you the same date twice.