Quartiere on Bank Street is cute!

New York Comedy Club is opening a Stamford location tomorrow, could be fun!

Park downtown go to Mecha put your name in for a table then if it’s a wait head across the street to Towne Parlor for a drink it’s generally pretty quiet earlier in the night. When mecha let’s you know your table is ready head back across the street and eat there.

Bonus: Avon theater is right there and there is a little park/ 16 handles to keep the date going.

Kouzina is a lot of fun! Plenty of action to distract from those awkward quiet moments in between convo.

Barcelona. You can go just cocktails, just wine, just apps or full meal. Need reservation on Friday/Saturday nights though. You'll see full families there with kids and a busy bar at the same time...it kind of does everything. Also this might sound weird but seeing how a stranger handles ordering shared plates can give you some insight into who they are.

Mecha, Flinders Lane and Kouzina are all solid restaurant choices too. You can go the Wheel for a more expensive option, but its pretty dam good. I'm not a fan of going hudson grill or Towne Parlor or any of those type of spots for a first date...they're basically bars that happen to have 'elevated' pub food.

During the summer Cisco brewing has s little outdoor setup with food trucks n music right on the water.

Lorca is perfect spot for coffee with plenty of lunch spots around if it goes well.

Nature center is great when its warm, its good excuse to 'walk n talk'. The Maritime Aquarium in Norwalk works for this too though it is packed with families on weekends. The Aquarium is also walking distance from the main drag in Norwalk so plenty of food options after.

Plenty of other parks you can go walk at in the area...Mianus in Stamford, Cranberry park in Norwalk Devils den in Weston, Ward in pound ridge.

EDIT; went to The Turning point's new downtown location this weekend. This is perfect space for a first date. Cool vibes. Lots of different types of seating set ups so it can be as casual as as you want it to be. Generally quiet. It has the typical millennial coffee shop Expensive-for-what-+it-is-but-pretty-tasty cafe food items and absolutely the best coffee in Stamford. Downside is you have to park at the mall if your driving and even though the rest of DT is close by, it's not a nice walk.

The Mecha suggestion is good in terms of keeping the casual "tone" but you'll have to slurp noodles in front of someone you don't know that well. I'd say Flinder's Lane on Summer Street has a similar vibe but more varied menu items (burgers, salad, pasta). The drinks are good too, but you can always leave and walk somewhere else. Depending on how things go you could walk through Mill River Park before choosing how to continue the evening.

As always, Third Place has a very casual vibe. They have a food truck rather than real dinner items, but it's a safe bet imo.

How about Third Place for a drink then T’s Wine Bar next door for dinner if the date is going well?

Had my first last date at Barcelona. Now we are married. It’s a fun, lively spot. Can’t go wrong.

Teff

Take her to colony, Brennan’s in shippan, vinnies on hope st. Walk in mill river, walk in myanus

Downtown has Lucky’s and Zaza which are both pretty good restaurants. You could go walk around the mall, although you’d be better off going to the Norwalk mall and maybe the aquarium over there. There’s the Avon theatre or majestic which are usually showing some cool stuff. That’s all I can think of off the top of my head

Hudson Table

Third Place - best casual first date vibe in town