Boys Don't Cry
In their instagram bio they call themselves an "elevated dive"... and that feels appropriate. Their well priced drinks and awesome Chinese snacks make this a solid LES spot. Oh, and if the date goes badly, remember Boy's Don't Cry (jk cry as much as you want, but actually don't because it was just a first date).
Seemingly designed for dates. they have 2 for $10 beer and 2 for $14 wine. Also reasonably priced cocktails.
Chinese bites from Nom Wah, hot dogs from Brooklyn Hot Dog and buttery popcorn.
Smallish space with bar seating, a few booths and a high top communal table. Not a ton of seats, but usually not too crowded so you should be good most nights.