With a friendly neighborhood vibe and an extensive wine and beer list, Fat Angel will let you show off your wine or beer knowledge without adding to the first-date pressure. And, assuming things are going nicely, a nice menu of charcuterie and small plates will keep the two of you at the table long enough to split another bottle.

The bustling vibe and clean, modern decor make Jane an inviting place for getting to know each other over a pastry or two. Grab one of the banquette tables near the front, or stake out an intimate spot in the loungy mezzanine and talk about how ridiculous it is that toast is still a thing.

If date two feels like it should be more low key than spendy, this rustic but unpretentious neighborhood spot will have you covered in the pizza and beer department, without skipping straight to Netflix & chill mode. Chef Nick Pallone moved down the street from his former post at Florio, and his emphasis on local ingredients, housemade charcuterie, and Neapolitan pies hits all the right notes without breaking the bank. A well-rounded lineup of craft beers and a modest, but nicely affordable wine list certainly doesn't hurt, either.

A hidden gem in Laurel Heights, Nico's inventive, five-course prix fixe menu changes nightly but always feels like a special occasion. Intimate and familiar, yet always fresh — the perfect spot to show you're serious about somebody, without adding the unnecessary gravitas of a big destination dinner.

Pizza makes for an unimpeachable date night standby, and Delfina makes inarguably solid Neapolitan-style pies. The vibe is nice enough to feel like a night out, but just neighborhood-y enough to feel comfortable. Get an extra salsiccia pie for bedtime snacking later.

The mid-century-inspired lobby bar at the Laurel Inn has a low-key vibe that will give you the Don Draper-sized ego you need to break the harsh news. Be forewarned though: The martinis here are voluminous and would look very dramatic being thrown in someone's face.