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.