Employees Only is a good idea. Their cocktails are great, and if you decide to eat, you can always get a table in back. They have a good food menu, both for a full dinner or just snacks (cheese plate, charcuterie). You could also go to Turks & Frogs on W 11th st. They only have beer and wine (a lot of interesting turkish wines), but also have a good menu of snack foods and it's an easy spot to hang out in for a lingering night.
As for the Spotted Pig, the crowds could be a problem, since it can be extremely tough to get a bar seat while you're waiting (sometimes up to an hour and a half or two hours) for a table, though if you can manage to get a bar seat or a table it would certainly be a fun date.
The Spotted Pig is cool and won't make it seem like you're trying too hard....
What you could do is have a cocktail at Employees Only and have food contingency plans at nearby places like Little Owl (reservations neccessary) or The Spotted Pig (there's a guaranteed 45 minute wait but you can have another drink while you're waiting for the table).
There's also Mary's Fish Camp, which takes walk-ins.
Lived in the WV for 2 yrs, but was at Mary's Fish Camp on Friday night for the first time...was great for a date. I like places that are interactive, or where the rest. can easily start off a conversation, i.e. decor, people, etc. Sat at the counter with view of the kitchen, waitstaff very friendly. Very fresh. The wait was 20 mins when everything else on West 4th was at least 45.
If you like fish, want something lite, simple, and easy...go for Mary's.
Spotted Pig great if you go a little later at night...but always crowded. If you think it's the kind of girl (assuming u r a guy) that can eat at the bar...would recommend the nudi, fries, and brugers are good. Grt bar upstairs...way to go
Barbuto nothing too fancy and great on a nice night like this when they have all of the doors open
Extra Virgin is also simple and clean, and have a good bar while you wait for your table