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Holiday Cocktail Lounge
Holiday Cocktail Lounge
Nick Solares

19 Reliable First Date Spots in Manhattan

Places that come off as effortlessly cool for get-to-know-you conversation

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Holiday Cocktail Lounge
| Nick Solares

A solid first-date spot has to hit some stringent requirements: It must be laid-back, yet impressive; casual, yet cool; and full, yet not crowded. These are the places in Manhattan that will always come through for first-date needs — trust.

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Note: Restaurants on this map are listed geographically.

1. Ruby's Vintage Harlem

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2340 Adam Clayton Powell Jr Blvd
New York, NY 10030
(212) 234-1833
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This hot and happening Harlem cocktail and wine bar is an ideal place to meet a date in the neighborhood. The mid-century chic space has both bar and banquette space, and there is some food such as hummus or mac and cheese if things are going well.

2. The Dakota Bar

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53 W 72nd St
New York, NY 10023
(212) 787-0700
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Lots of seating at both a large bar and high-tops surrounding, plus a full cocktail list make Dakota Bar a go-to first-date spot on the Upper West Side. On warm evenings, the wraparound windows are thrown open.

Dakota Bar Dakota Bar [Official Photo]

3. The Penrose

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1590 2nd Ave
New York, NY 10028
(212) 203-2751
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One of the better bars on the Upper East Side, the Penrose is sure to be bumping on weeknights. Plus, there are plenty of small food options for sharing (or not sharing). It can get pretty crowded, so have Bondurants a few blocks up as a backup.

4. Lillie's Victorian Establishment

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249 W 49th St
New York, NY 10019
(212) 957-4530
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There are plenty of drink options in this classy yet fun, and very long, Victorian-style bar. Like the Union Square original, Lillie’s in Hell’s Kitchen is an easy meeting spot in an area where there aren’t many.

Lillie’s Lillie’s [Official Photo]

5. Empellon Al Pastor (Murray Hill)

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145 E 39th St
New York, NY 10016
(212) 865-5800
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Alex Stupak’s lively restaurant is a fun and casual pick for a first date bar, with margaritas and tacos to match. It’s ideal if both people work or live in Midtown and want something that isn’t an Irish bar.

6. Oscar Wilde

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45 W 27th St
New York, NY 10001
(212) 213-3066
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The owners of Lillie’s use a similar formula at Oscar Wilde of over-the-top decor, tons of seating, and reliable cocktails to lure in everyone from birthday parties to dates. It’s a huge place, so it’s easy to find a spot and blend into the crowds while getting to know someone new.

Oscar Wilde Oscar Wilde [Official Photos]

7. The Tippler

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425 W 15th St
New York, NY 10011
(212) 206-0000
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Arrive in the early evening at this bar underneath Chelsea Market to snag a pair of barstools. If the date is going well, head upstairs for tacos from Los Tacos No. 1. Note that the phone service here is spotty, in case there is a friend who is going to call for last-minute help feeding her dog.

The Tippler The Tippler [Official Photo]

8. Pete's Tavern

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129 E 18th St
New York, NY 10003
(212) 473-7676
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A casual bar near Union Square isn’t easy to find, but Pete’s Tavern is it. It’s been open since 1864, so there’s plenty of history to fall back on if conversation isn’t flowing. There’s also plenty of beer.

Pete’s Tavern Pete’s Tavern [Official Photo]

9. Katana Kitten

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531 Hudson St
New York, NY 10014
(212) 243-3007
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There are two disparate spaces to choose from at this Japanese-inflected West Village bar. Upstairs find a more refined cocktail lounge area, or head down for a more raucous, basement-style experience. Cocktail fiends will find plenty to love about this place, like a shiso gin and tonic.

Katana Kitten has a bar to the right with stools and lights hanging above Katana Kitten [Official Photo]

10. Wilfie & Nell

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228 West 4th Street
New York, NY 10014
(212) 242-2990
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Pub-like Wilfie and Nell will be full of other first dates to blend right into. It’s casual and comfortable, yet easy for observing other couples and their body language. If it happens to be too full, there are plenty of other options in the immediate vicinity: Bar Sardine, Fairfax, Due West, and While We Were Young.

11. Holiday Cocktail Lounge

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75 St Marks Pl
New York, NY 10003
(212) 777-9637
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This longtime East Village dive got a facelift back in 2015, but the laid-back spirit of the place remains. Drink options are plentiful, while the bartenders are friendly, but not too chatty. The buzzy bar offers a mixed bag of bar food — burger, disco fries, wings — if all goes well. Here’s a fun fact to get convo flowing: One of the bar’s owners created the Pirate’s Booty snack.

Holiday Cocktail Lounge Nick Solares

12. Swift Hibernian Lounge

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34 E 4th St
New York, NY 10003
(212) 260-3600
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At its core, Swift Hibernian Lounge is an Irish pub, but everything at this Noho spot is just a little bit better than the average, with a solid beer selection, $13 cocktails, and warm, historic decor (seating is reclaimed church pews and a pulpit from a church in Ireland). The magic formula is that it’s casual, always bustling, and charming. This is the Eater go-to first date winner.

13. Joyface

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104 Loisaida Ave
New York, NY 10009
(917) 261-2166
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This ’70s-styled Alphabet City bar has plenty of intimate seating and conversational pieces — namely, the water bed, old pin-ups on the wall, and a jar with cocktail names on pieces of paper that one can pick at random. Bop across the street to Loverboy if a second venue is in the cards.

14. Mother's Ruin

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18 Spring St
New York, NY 10012

Sweet & Vicious and Mother’s Ruin are two Spring Street bars that pack them in during weekends, but are found to be much quieter for a weekday first date. At the latter, a food menu is on hand if the date goes so well that it’s now 1 a.m. and hunger strikes.

15. Casa Mezcal

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86 Orchard St
New York, NY 10002
(212) 777-2661
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On the quiet side of Orchard Street, this cantina provides a fun and vibrant setting for a first date with moody lighting and playful decor. There’s a big bar and high-top seating to choose from. Linger for hours over a flight of mezcal, if the attraction’s there.

16. Weather Up

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159 Duane St
New York, NY 10013
(212) 766-3202
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A long and often very busy Tribeca bar with friendly and engaging bartenders, Weather Up has a cocktail list that is sure to get the evening going. Post-work, the place is likely to be filled with bankers, but it’s a solid choice for later evening meet-ups.

Weather Up Weather Up [Official Photo]

17. Whiskey Tavern

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79 Baxter St A
New York, NY 10013
(212) 374-9119
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The unassuming digs at this Chinatown dive are an unpretentious setting for a first date, plus there are games and it closes at 4 a.m., so there’s no rush to part ways. If the date is going well, head to nearby Great NY Noodletown for classic late night eats.

Whiskey Tavern Whiskey Tavern [Official Photo]

18. 169 Bar

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169 E Broadway
New York, NY 10002
(646) 833-7199
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There are no dull moments at this divey bar that has chosen palm trees and leopard prints as its decor. No matter the day, the vibe at 169 is laid-back yet bustling. Plus, ordering a bag of popcorn to the table is an option. PBR is the beer of choice here, and pickleback the shot. Warning: It can get loud.

19. The Dead Rabbit Grocery and Grog

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30 Water St
New York, NY 10004
(646) 422-7906
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It’s been called the world’s best bar, and it’s a memorable first-date spot. Whether in the casual taproom or the upstairs parlor, enjoy more than one of the Dead Rabbit’s always-stellar cocktails. Be prepared for crowds.

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1. Ruby's Vintage Harlem

2340 Adam Clayton Powell Jr Blvd, New York, NY 10030

This hot and happening Harlem cocktail and wine bar is an ideal place to meet a date in the neighborhood. The mid-century chic space has both bar and banquette space, and there is some food such as hummus or mac and cheese if things are going well.

2340 Adam Clayton Powell Jr Blvd
New York, NY 10030

2. The Dakota Bar

53 W 72nd St, New York, NY 10023
Dakota Bar Dakota Bar [Official Photo]

Lots of seating at both a large bar and high-tops surrounding, plus a full cocktail list make Dakota Bar a go-to first-date spot on the Upper West Side. On warm evenings, the wraparound windows are thrown open.

53 W 72nd St
New York, NY 10023

3. The Penrose

1590 2nd Ave, New York, NY 10028

One of the better bars on the Upper East Side, the Penrose is sure to be bumping on weeknights. Plus, there are plenty of small food options for sharing (or not sharing). It can get pretty crowded, so have Bondurants a few blocks up as a backup.

1590 2nd Ave
New York, NY 10028

4. Lillie's Victorian Establishment

249 W 49th St, New York, NY 10019
Lillie’s Lillie’s [Official Photo]

There are plenty of drink options in this classy yet fun, and very long, Victorian-style bar. Like the Union Square original, Lillie’s in Hell’s Kitchen is an easy meeting spot in an area where there aren’t many.

249 W 49th St
New York, NY 10019

5. Empellon Al Pastor (Murray Hill)

145 E 39th St, New York, NY 10016

Alex Stupak’s lively restaurant is a fun and casual pick for a first date bar, with margaritas and tacos to match. It’s ideal if both people work or live in Midtown and want something that isn’t an Irish bar.

145 E 39th St
New York, NY 10016

6. Oscar Wilde

45 W 27th St, New York, NY 10001
Oscar Wilde Oscar Wilde [Official Photos]

The owners of Lillie’s use a similar formula at Oscar Wilde of over-the-top decor, tons of seating, and reliable cocktails to lure in everyone from birthday parties to dates. It’s a huge place, so it’s easy to find a spot and blend into the crowds while getting to know someone new.

45 W 27th St
New York, NY 10001

7. The Tippler

425 W 15th St, New York, NY 10011
The Tippler The Tippler [Official Photo]

Arrive in the early evening at this bar underneath Chelsea Market to snag a pair of barstools. If the date is going well, head upstairs for tacos from Los Tacos No. 1. Note that the phone service here is spotty, in case there is a friend who is going to call for last-minute help feeding her dog.

425 W 15th St
New York, NY 10011

8. Pete's Tavern

129 E 18th St, New York, NY 10003
Pete’s Tavern Pete’s Tavern [Official Photo]

A casual bar near Union Square isn’t easy to find, but Pete’s Tavern is it. It’s been open since 1864, so there’s plenty of history to fall back on if conversation isn’t flowing. There’s also plenty of beer.

129 E 18th St
New York, NY 10003

9. Katana Kitten

531 Hudson St, New York, NY 10014
Katana Kitten has a bar to the right with stools and lights hanging above Katana Kitten [Official Photo]

There are two disparate spaces to choose from at this Japanese-inflected West Village bar. Upstairs find a more refined cocktail lounge area, or head down for a more raucous, basement-style experience. Cocktail fiends will find plenty to love about this place, like a shiso gin and tonic.

531 Hudson St
New York, NY 10014

10. Wilfie & Nell

228 West 4th Street, New York, NY 10014

Pub-like Wilfie and Nell will be full of other first dates to blend right into. It’s casual and comfortable, yet easy for observing other couples and their body language. If it happens to be too full, there are plenty of other options in the immediate vicinity: Bar Sardine, Fairfax, Due West, and While We Were Young.

228 West 4th Street
New York, NY 10014

11. Holiday Cocktail Lounge

75 St Marks Pl, New York, NY 10003
Holiday Cocktail Lounge Nick Solares

This longtime East Village dive got a facelift back in 2015, but the laid-back spirit of the place remains. Drink options are plentiful, while the bartenders are friendly, but not too chatty. The buzzy bar offers a mixed bag of bar food — burger, disco fries, wings — if all goes well. Here’s a fun fact to get convo flowing: One of the bar’s owners created the Pirate’s Booty snack.

75 St Marks Pl
New York, NY 10003

12. Swift Hibernian Lounge

34 E 4th St, New York, NY 10003

At its core, Swift Hibernian Lounge is an Irish pub, but everything at this Noho spot is just a little bit better than the average, with a solid beer selection, $13 cocktails, and warm, historic decor (seating is reclaimed church pews and a pulpit from a church in Ireland). The magic formula is that it’s casual, always bustling, and charming. This is the Eater go-to first date winner.

34 E 4th St
New York, NY 10003

13. Joyface

104 Loisaida Ave, New York, NY 10009

This ’70s-styled Alphabet City bar has plenty of intimate seating and conversational pieces — namely, the water bed, old pin-ups on the wall, and a jar with cocktail names on pieces of paper that one can pick at random. Bop across the street to Loverboy if a second venue is in the cards.

104 Loisaida Ave
New York, NY 10009

14. Mother's Ruin

18 Spring St, New York, NY 10012

Sweet & Vicious and Mother’s Ruin are two Spring Street bars that pack them in during weekends, but are found to be much quieter for a weekday first date. At the latter, a food menu is on hand if the date goes so well that it’s now 1 a.m. and hunger strikes.

18 Spring St
New York, NY 10012

15. Casa Mezcal

86 Orchard St, New York, NY 10002

On the quiet side of Orchard Street, this cantina provides a fun and vibrant setting for a first date with moody lighting and playful decor. There’s a big bar and high-top seating to choose from. Linger for hours over a flight of mezcal, if the attraction’s there.

86 Orchard St
New York, NY 10002

Related Maps

16. Weather Up

159 Duane St, New York, NY 10013
Weather Up Weather Up [Official Photo]

A long and often very busy Tribeca bar with friendly and engaging bartenders, Weather Up has a cocktail list that is sure to get the evening going. Post-work, the place is likely to be filled with bankers, but it’s a solid choice for later evening meet-ups.

159 Duane St
New York, NY 10013

17. Whiskey Tavern

79 Baxter St A, New York, NY 10013
Whiskey Tavern Whiskey Tavern [Official Photo]

The unassuming digs at this Chinatown dive are an unpretentious setting for a first date, plus there are games and it closes at 4 a.m., so there’s no rush to part ways. If the date is going well, head to nearby Great NY Noodletown for classic late night eats.

79 Baxter St A
New York, NY 10013

18. 169 Bar

169 E Broadway, New York, NY 10002

There are no dull moments at this divey bar that has chosen palm trees and leopard prints as its decor. No matter the day, the vibe at 169 is laid-back yet bustling. Plus, ordering a bag of popcorn to the table is an option. PBR is the beer of choice here, and pickleback the shot. Warning: It can get loud.

169 E Broadway
New York, NY 10002

19. The Dead Rabbit Grocery and Grog

30 Water St, New York, NY 10004

It’s been called the world’s best bar, and it’s a memorable first-date spot. Whether in the casual taproom or the upstairs parlor, enjoy more than one of the Dead Rabbit’s always-stellar cocktails. Be prepared for crowds.

30 Water St
New York, NY 10004

Related Maps