Date Night in Downtown Indy: Your Ultimate Guide

Cocktails, Cozy Vibes & a Little Friendly Competition

Planning a date night that’s equal parts stylish, laid-back, and memorable? Whether you're trying to impress someone new or just shake up your usual routine, this downtown Indy itinerary delivers a full evening of connection, conversation, and fun — no awkward planning required.

🍸 First Stop: Cocktails at The Oakmont

555 Massachusetts Ave, Indianapolis, IN 46204
Happy Hour: 4–6 PM | Reservations Recommended

Kick off your night at one of the chicest spots in the city, The Oakmont. It’s trendy without trying too hard — and the cocktail game is strong. Grab a seat at the bar or on the covered patio and sip something smooth like the Oakmont Old Fashioned or a Lavender Lemon Drop. The happy hour menu features shareable small plates that are perfect if you want to nibble without spoiling dinner.

Pro tip: Ask for a corner table near the windows for cozy people-watching and great lighting if you're snapping a selfie.

🍽️ Main Course: Dinner at Vida

601 E New York St, Indianapolis, IN 46202
Dinner Service: 5–10 PM | Reservations Required

From the moment you walk in, Vida sets the tone with a warm, romantic ambiance and exceptional service. As one of Indy’s only AAA Four Diamond restaurants, it strikes that rare balance between upscale and inviting. You’ll have space to chat without shouting, and the menu — featuring locally-sourced, seasonal dishes — is perfect for sharing bites and savoring flavors together.

Choose the tasting menu if you want the full experience or order à la carte for a more flexible pace. Either way, don’t skip the bread service or the wine wall.

Vibe Check: It’s elevated without being stuffy. Dress like you care, but no need to go full black tie.

🍨 Sweet Stop: Dessert at Lick Ice Cream

Bottleworks District – 850 Massachusetts Ave, Indianapolis, IN 46204
Open Until 10 PM | No reservation needed

Indulge in handcrafted small-batch ice cream at Lick, just steps away from your final stop. Their bold flavors (like Goat Cheese & Cherry or Whiskey Hazelnut) are creative without being gimmicky — and their waffle cones are made fresh daily. Grab your treat and take a short stroll around the Bottleworks District for a sweet intermission before the grand finale.

Insider Tip: Split a flight of mini scoops to sample more flavors together — it’s a built-in excuse to share.

🎯 End the Night: Games & Laughter at Pins Mechanical Co.

856 Carrollton Ave, Indianapolis, IN 46202 (Bottleworks District)
Open Until 2:30 AM Fri & Sat | No reservation required

Wind down the night with a little friendly competition at Pins Mechanical Co. This retro-inspired arcade and duckpin bowling spot is packed with nostalgia, laughter, and good vibes. Whether you're battling it out in a game of skee-ball, trying to impress with pinball skills, or teaming up for duckpin bowling, it’s the kind of fun that brings out everyone's playful side.

Grab a boozy slushie or a local craft beer and keep the energy going with a side of silliness.

Bonus: Since Lick and Pins are both in Bottleworks, there’s zero time wasted getting from dessert to fun.

How to Book It All

• The Oakmont: Reserve on OpenTable

• Vida: Book your table here

• Lick Ice Cream: Walk-in friendly

• Pins Mechanical: Walk-in friendly, but weekends fill fast

Final Thoughts

This curated date night is designed to keep the energy flowing — no awkward lulls, just a blend of ambiance, flavor, and fun. Whether you're rekindling something special or just starting something new, Indy’s downtown scene makes it easy to impress. All you have to do is show up.