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Where to meet halfway between Midtown South, Flatiron & Union Square and Midtown & Times Square

Midtown South, Flatiron & Union Square and Midtown & Times Square are about 1.1 miles apart. The fairest first date spots are around Midtown & Times Square, roughly 0.5 miles from each of you. For a drink, try The Ragtrader Bo Peep NYC; for coffee, Fork & Spoon.

For drinks

Ordered so neither of you has the longer trip by much. Miles are as the crow flies.

  1. The Ragtrader Bo Peep NYC

    Cocktail bar

    0.5 mi from Midtown South, Flatiron & Union Square · 0.5 mi from Midtown & Times Square

    ~3 min from 34 St-Herald Sq (B D F M N Q R W)MapWebsite

  2. SkyLawn Bar

    Cocktail bar

    0.5 mi from Midtown South, Flatiron & Union Square · 0.5 mi from Midtown & Times Square

    ~4 min from 34 St-Herald Sq (B D F M N Q R W)MapWebsite

  3. Habanero Blues

    Cocktail bar

    0.5 mi from Midtown South, Flatiron & Union Square · 0.5 mi from Midtown & Times Square

    ~4 min from 34 St-Herald Sq (B D F M N Q R W)MapWebsite

  4. Top of the Strand Rooftop Bar

    Cocktail bar

    0.6 mi from Midtown South, Flatiron & Union Square · 0.5 mi from Midtown & Times Square

    ~5 min from 34 St-Herald Sq (B D F M N Q R W)MapWebsite

  5. The Ginger Man

    Beer bar

    0.5 mi from Midtown South, Flatiron & Union Square · 0.6 mi from Midtown & Times Square

    ~6 min from 33 St (6)MapWebsite

For coffee

  1. Fork & Spoon

    Café

    0.5 mi from Midtown South, Flatiron & Union Square · 0.6 mi from Midtown & Times Square

    ~5 min from 34 St-Herald Sq (B D F M N Q R W)MapWebsite

  2. Cafe 37

    Café

    0.6 mi from Midtown South, Flatiron & Union Square · 0.5 mi from Midtown & Times Square

    ~5 min from 34 St-Herald Sq (B D F M N Q R W)MapWebsite

  3. Toast Cafe Brasserie

    Café

    0.5 mi from Midtown South, Flatiron & Union Square · 0.6 mi from Midtown & Times Square

    ~2 min from 34 St-Herald Sq (B D F M N Q R W)MapWebsite

  4. New City Cafe

    Café

    0.5 mi from Midtown South, Flatiron & Union Square · 0.6 mi from Midtown & Times Square

    ~3 min from 34 St-Herald Sq (B D F M N Q R W)MapWebsite

  5. W Cafe

    Café

    0.5 mi from Midtown South, Flatiron & Union Square · 0.6 mi from Midtown & Times Square

    ~5 min from 34 St-Herald Sq (B D F M N Q R W)MapWebsite

Or meet on one side

If one of you doesn’t mind the trip, each neighborhood has its own list.

Midtown South, Flatiron & Union SquareManhattan · 133 bars · 59 coffee spotsMidtown & Times SquareManhattan · 234 bars · 103 coffee spots

Questions

People also ask

Where is halfway between Midtown South, Flatiron & Union Square and Midtown & Times Square?

The two are about 1.1 miles apart as the crow flies. The spots where both of you travel about the same distance are mostly around Midtown & Times Square.

What’s a good first date spot between Midtown South, Flatiron & Union Square and Midtown & Times Square?

The Ragtrader Bo Peep NYC is 0.5 mi from Midtown South, Flatiron & Union Square and 0.5 mi from Midtown & Times Square. SkyLawn Bar is another fair choice for drinks. For coffee, Fork & Spoon works for both of you.

Why meet in the middle for a first date?

Neither person carries the whole trip, so it reads as considerate rather than convenient for one side. Suggest the place with both travel times in mind, and offer to swap it if it doesn’t suit them.

More places to meet halfway

East Village ↔ Midtown South, Flatiron & Union Square1.3 mi apart · fair spots in betweenGreenwich Village ↔ Midtown South, Flatiron & Union Square1.0 mi apart · fair spots in betweenMidtown South, Flatiron & Union Square ↔ West Village1.1 mi apart · fair spots in betweenHell's Kitchen ↔ Midtown South, Flatiron & Union Square1.4 mi apart · fair spots in betweenEast Midtown & Turtle Bay ↔ Midtown South, Flatiron & Union Square1.4 mi apart · fair spots in betweenMidtown & Times Square ↔ Murray Hill & Kips Bay1.0 mi apart · fair spots in between

How this list is made: spots are open, independent cafés, bars and restaurants, chosen for being close to the subway and on blocks with plenty of other places nearby. Nobody pays to be listed. Distances are straight-line and walking times are estimates, so check opening hours before you go. Updated 2026-10-13. Data: Places: Overture Maps Foundation (CDLA-Permissive-2.0); 2020 Neighborhood Tabulation Areas, NYC Department of City Planning (NYC Open Data); MTA Subway Stations (data.ny.gov); Parks Properties, NYC Parks (NYC Open Data).