"When your ideal date night involves a few excellent pours of fermented grapes, head to Easy Does It in Logan Square. It’s unpretentious and casual, so even if you have no clue what "terroir" is, it’s still a fun place to drink and hang. They have a fantastic wine selection, with approachable descriptions like “It’s Clementime” or “Earth Jam.” Easy Does It has plenty of seating whether you’re a table and booth person, or would rather sip on orange wine while sinking into a comfy chair. Weekdays are a bit more relaxed with occasional live jazz, but if dancing is also part of your ideal date, come for a late-night weekend DJ set." - adrian kane, john ringor