Flatiron First Date Ideas

She's in fashion in the Garment District. You're turning comments in Midtown East.
Flatiron offers tight spreads: good drinks, good food, low volatility. Just what you need on a Wednesdsay.

Best First-Date Bars in Flatiron

Be wary soldier, it's a first date

Casual first drink 🍸

The Ivory Peacock: Website

Address: 38 W 26th St

Happy Hour: No HH

Expected Check: $50-70 (2 drinks each)

Reservations: Resy

Move to light bites? 🥟

Lulla: Website

Address: 113 W 24th St

Happy Hour: Aperitivo Hour Daily 3-7pm

Expected Check: $70-90 (1 drink/pp + apps)

Reservations: Recommended - Resy

Ditch 'n Drink 🍺

Store House: Website

Address: 757 6th Ave

Happy Hour: No HH

Expected Check: $40-60 (2-3 drinks each)

Reservations: Not necessary

📍 Venue Locations & Walking Directions

Hinge match out of my league, step it up

Fancy dinner 🍽️

Borgo: Website

Address: 124 E 27th St

Happy Hour: No HH

Expected Check: $130-200 (dinner + drinks)

Reservations: Recommended - Resy

Seal the Deal

Bar Calico: Website

Address: 23 Lexington Ave, 2nd Floor (Freehand Hotel)

Happy Hour: No HH

Expected Check: $60-80 (2 drinks each)

Reservations: Recommended - Resy

📍 Venue Locations & Walking Directions

Walkable First-Date Flows

🔮 Flatiron date vibes

Polished but not stuffy. She's in fashion, you're in finance—Flatiron is the neutral ground. Tight spreads: good drinks, good food, low volatility. Perfect for Wednesday dates when you both have early meetings.

💸 How much will this neighborhood set me back?

Mid-range with options. Borgo dinner can hit $150-200 for two, but you can also do The Ivory Peacock for $50-70 in drinks. Store House keeps it reasonable. Lulla has Aperitivo Hour 3-7pm daily with $12 cocktails and $10 wine.

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